Vol 31 Photochemistry

Contents
Introduction and Review of the Year By Andrew Gilbert Part I Physical Aspects of Photochemistry Photophysical Processes in Condensed Phases By Anthony Harriman
1
13
15
15
1 Introduction
2 General Aspects of Photophysical Processes 3 Kinetic and Theoretical Considerations 4 Photophysical Processes in Liquid or Solid Media 4.1 Detection of Single Molecules 4.2 Radiative and Non-radiative Decay Processes 4.3 Amplitude or Torsional Motion 4.4 Quenching of Excited States 4.4.1 Electron-transfer Reactions 4.4.2 Energy-transfer Reactions 4.5 Photophysics of Fullerenes
5 Applications of Photophysics
15
17
18 19 19 20 21 21 22 23
24 26
28
6 Advances in Instrument Design and Utilization
References
Part I1 Organic Aspects of Photochemistry
45 47
Chapter 1 Photolysis of Carbonyl Compounds By William M. Horspool
1 Norrish Type I Reactions

Photochemistry, Volume 3 1 0The Royal Society of Chemistry, 2000
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47
vi
Contents
2 Norrish Type I1 Reactions 2.1 1,5-Hydrogen Transfer 2.2 Other Hydrogen Transfers 3 Oxetane Formation 4 Miscellaneous Reactions 4.1 SET Processes 4.2 Decarbonylation and Decarboxylation 4.3 Reactions of Miscellaneous Haloketones and Acid Chlorides 4.4 Other Fission Processes
References
50 50 55
57 61 61
64
67 69 71
75
Chapter 2 Enone Cycloadditionsand Rearrangements: Photoreactions of Dienones and Quinones By W l i m M. Horspool ila
1 Cycloaddition Reactions 1.1 Intermolecular Cycloaddition 1.1.1 Open-chain Systems 1.1.2 Additions to Cyclopentenones and Related Systems 1.1.3 Additions to Cyclohexenones and Related Systems 1.2 Intramolecular Additions 1.2.1 Intramolecular Additions to Cyclopentenones 1.2.2 Additions to Cyclohexenones and Related Systems
2 Rearrangement Reactions 2.1 a,P-Unsaturated Systems 2.1,l Isomerisation 2.1.2 Hydrogen Abstraction Reactions 2.1.3 Rearrangement Reactions 2.2 P,y-Unsaturated Systems 2.2.1 The Oxa Di-n-methane Reaction and Related Processes
3 Photoreactions of Thymines and Related Compounds 3.1 Photoreactions of Pyridones 3.2 Photoreactions of Thymines etc. 3.3 Miscellaneous Processes
75 75 75 76 80 81 83 83 86 86 86 86 87 88 88 89 89 90 93
Contents
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4 Photochemistry of Dienones 4.1 Cross-conjugated Dienones 4.2 Linearly Conjugated Dienones
93 93 95 96 96 99 100 101 103 104 104 104 106

112
1,2-, 1,3- and 1,4-Diketones 5.1 Reactions of 1,2-Diketones and other 1,2-Dicarbonyl Compounds 5.2 Reactions of 1,3-Diketones 5.3 Reactions of 1,4-Diketones 5.3.1 Phthalimides and Related Compounds 5.3.2 Fulgides and Fulgimides
6 Quinones 6.1 o-Quinones 6.2 p-Quinones References Chapter 3 Photochemistry of Alkenes, Alkynes and Related Compounds By William M. Horspool 1 Reactions of Alkenes 1.1 cis,trans-Isomerisation 1.1.1 Stilbenes and Related Compounds 1.1.2 The Dithienylethene System and Related Compounds 1.2 Miscellaneous Reactions 1.2.1 Addition Reactions 1.2.2 Electron Transfer Processes 1.2.3 Other Processes 2 Reactions Involving Cyclopropane Rings '2.1 The Di-n-methane Rearrangement and Related Processes 2.1.1 The Aza-di-n-methane Rearrangement and Related Processes 2.1.2 SET Induced Reactions 2.2 Miscellaneous Reactions Involving Three-membered Ring Compounds 3 Reactions of Dienes and Trienes 3.1 Vitamin D Analogues 4 (2+2)-Intramolecular Additions
112 112 113 116 120 120 122 122 124 124 125 125 127 128 132 133
Vlll
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Contents
5 Dimerisation
6 Miscellaneous Reactions 6.1 Reactions Involving Cations and Radicals 6.2 Miscellaneous Rearrangements and Bond Fission Processes References Chapter 4 Photochemistry of Aromatic Compounds By Alan Cox
1 Introduction
134 137 137 138 140

145
145 145 154 163 165 171 175 176 182
2 Isomerisation Reactions
3 Addition Reactions
4 Substitution Reactions
5 Cyclisation Reactions
6 Dimerisation Reactions
7 Lateral Nuclear Shifts 8 Miscellaneous Photochemistry
References Chapter 5 Photo-reduction and -oxidation By Alan Cox

1 Introduction
193
193 193
2 Reduction of the Carbonyl Group

3
Reduction of Nitrogen-containing Compounds Miscellaneous Reductions
202 205 209 21 1

217
5 Singlet Oxygen
6 Oxidation of Aliphatic Compounds
7 Oxidation of Aromatic Compounds
Contents
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8 Oxidation of Nitrogen-containing Compounds

9 Miscellaneous Oxidations
References
220 225 226
Chapter 6 Photoreactionsof CompoundsContaining Heteroatoms Other than Oxygen By William M.Horspool and Albert C. Pratt
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234 235 235 238 244 244 245 245 25 1 256 27 1 277 277 280 283 285
1 Introduction 2 Nitrogen-containing Compounds 2.1 E,Z-Isomerisations 2.2 Photocyclisations 2.3 Photoadditions 2.3.1 Intramolecular Processes 2.3.2 Intermolecular Processes 2.3.3 Other Addition Reactions 2.4 Rearrangements 2.5 Other Processes 3 Sulfur-containing Compounds 4 Compounds Containing Other Heteroatoms 4.1 Silicon and Germanium 4.2 Phosphorus 4.3 Other Elements
References
Chapter 7 Photoelimination By Ian R Dunkin

1 Introduction
2 w
297 297 299 299 300 302
2 Elimination of Nitrogen from Azo Compounds and Analogues 3 Elimination of Nitrogen from Diazo Compounds and Diazirines 3.1 Generation of Alkyl and Alicyclic Carbenes 3.2 Generation of Aryl Carbenes 3.3 Photolysis of a-Diazo Carbonyl Compounds
Contents
4 Elimination of Nitrogen from Azides and Related Compounds 4.1 Aryl Azides 4.2 Heteroaryl Azides
303 304 307

307
5 Photoelimination of Carbon Monoxide and Carbon Dioxide 5.1 Photoelimination of CO and CO;! from Organometallic Compounds
6 Photoelimination of NO and NO;! 7 Miscellaneous Photoelimination and Photofragmentations 7.1 Photoelimination from Hydrocarbons 7.2 Photoelimination from Organohalogen Compounds 7.3 Photofragmentations of Organosilicon and Organogermanium Compounds 7.4 Photofragmentations of Organosulfur and Organoselenium Compounds 7.5 Photolysis of o-Nitrobenzyl Derivatives 7.6 Other Phot ofragmentations
309 312 3 14 314 314 317 3 19 321 322 324
References
Part 111 Polymer Photochemistry By Norman S. Allen
1 Introduction
333
335 335 336 340 345 346 357 357 358 359 359 359 360 360 360
2 Photopolymerisation 2.1 Photoinitiated Addition Polymerisation 2.2 Photocrosslinking 2.3 Photografting 3 Luminescence and Optical Properties 4 Photodegradation and Photooxidation Processes in Polymers 4.1 Polyolefins 4.2 Poly(viny1halides) 4.3 Poly(acry1ates) and (alkyl acrylates) 4.4 Polyamides and Polyimides 4.5 Poly(a1kyl and aromatic ethers) 4.6 Silicone Polymers 4.7 Polystyrenes and Copolymers 4.8 Polyurethanes and Rubbers
Contents
xi
4.9 4.10 4.1 1 4.12
5
Polyesters Photoablation of Polymers Natural Polymers Miscellaneous Polymers
360 360 36 1 36 1 362 363 364 393 395 395 396 398 399
400 400 403
Photostabilisation of Polymers
6 Photochemistry of Dyed and Pigmented Polymers
References
Part IV Photochemical Aspects of Solar Energy Conversion By Alan Cox
1 Introduction
2 Homogeneous Photosystems
3 Heterogeneous Photosystems
4 Photoelectrochemical Cells
5 Biological Systems
6 Luminescent Solar Concentrators
References Author Index
Part III
Polymer Photochemistry
By Norman S. Allen
Polymer Photochemistry
BY NORMAN S. ALLEN
Introduction
The eld of polymer photochemistry continues to play a major role in photochemistry with many new areas of academic interest and industrial development. Photolithography continues to be developed particularly with regard toward designing systems for molecular devices. Interest in active ionic initiators and radical/ionic processes continues while the photocrosslinking of polymers is attractive in terms of enhancing the physical and mechanical properties of materials. The optical properties of polymers, particularly the use of probes and excimer formation continues to be an active area as a means of studying their macromolecular structure, energy migration and molecular mobility. Polymer interactions and behavioural features in micellar media provide a valuable probe for determining molecular sizes and forces in surfactant systems. In fact, over fty articles have been devoted to this topic in the last review period. In terms of growth, interest in polymeric light emitting diodes has increased at a phenomenal rate, since there are obvious commercial implications. Within the last review period there have been over eighty articles dealing alone with this topic. Further developments in terms of expansion have seen a major shift toward photochromic materials and liquid crystalline polymers. The photooxidation of polymers on the other hand continues to decline in attention although there is special interest in natural cellulosic-based materials. Bio- and photodegradable plastics are important for agricultural usage although interest here is again in decline. The same applies to polymer stabilisation where commercial applications dominate very much with much emphasis on the practical use of stabilisers. For dyes and pigments stability continues to be a major issue. 2 Photopolymerisation
Activity in a eld is often a reection of the number and variety of papers that have appeared of a topical or review nature. This last year has seen less than twenty articles to date, slightly less than the previous review period. An extensive review has appeared on the function of different types of photoPhotochemistry, Volume 31 # The Royal Society of Chemistry, 2000 335
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Photochemistry
initiators and their future development1. A number of articles have targeted interest in photosensitive polymers2, novel highly catalytic systems3, cyclisation systems4, vinyl ether materials5, stereolithography6, organometallic7 and redox initiators8. Ring opening metathesis by ruthenium complexes9 has been reviewed for the formulation of positive tone high resolution microresists10 as have electron photoejection processes11 and volatile initiator fragments12. Cationic photoinitiation has been covered in depth13 as have vinyl polymerisations14, sulfonium initiators15 and polymeric initiators with benzophenone side groups16. 2.1 Photoinitiated Addition Polymerisation Many new photoinitiator systems continue to be developed. Three novel water soluble copolymers with pendant benzil groups have been synthesised and characterised17. The polymeric systems were found somewhat more reactive for photoinducing polymerisation than the corresponding monomeric structure. Ketyl radical formation by hydrogen atom abstraction was the prime mechanism with the radical anion being formed through a triplet exciplex in the presence of an amine cosynergist.
CO CO O CH2 CH2 O CO MBz Me CH2 C O CH2 CH2 O Bz Me CH2 C O CH2 CH2 O Bz Me CH2 C O CH2 CH2 O Bz co CO AAm CO
n n n
C Me
CH2
CH2 CH COO
Me CH2 CH2 N+ Me, Cl Me
C O
CO co Cl
CO
CH2 CH
Me C Me CH2 SO3, Na+
C O
CO NH
CO co SO3Na
CO
CH2 CH NH2
C O
C O
III: Polymer Photochemistry
337
Novel structural derivatives of thioxanthone continue to be developed with a number of 1-chloro-4-oxy derivatives having been synthesised.18 Alkoxy subsitution in the 4-position of the molecule enhances the rate of photoinduced polymerisation in visible light with the 4-hydroxy derivative exhibiting least activity. The 1-chloro group was also implicated in the photoreactions in undergoing direct photolysis and forming active chlorine radicals. This gave rise to high polymerisation activity in the presence of oxygen. A number of novel water soluble derivatives of thioxanthone have also been developed19,20. Those with hydroxyethylaminopropoxy groups were found to be effective in the absence of an amine co-synergist. A series of novel alkyl and phenylthio derivatives of benzophenone have been found to be highly effective photoinitiators through side chain scission to give alkyl and thio radicals21,22. Those with sulfoxide groups, however, were found to be less effective. Dialkyldithiocarbamate derivatives have been found to give rise to living free radical polymerisations23 using butyl acrylate as an example while a series of thiobenzoate derivatives show high activity dependent upon the nature of the substitution24. A series of polymer bound hydroxamic dithiobenzoic anhydride compounds have been found to be very effective heterogeneous photoinitiators25. The photopolymerisation of vinyl monomers has been successfully carried out using a two-phase solvent system with tetrabuylammonium chloride-KSCN system in carbon tetrachloride26. In the solid phase on the other hand vinyl monomers can be photopolymerised on photocatalytic surfaces with CDS27. In the camphorquinone initiated polymerisation of acrylates oxygen has been found to accelerate the rate possibly through some type of oxidation complex assisting the process28. Thionine requires an amine for photoinducing polymerisations29 with a maximum rate at 0.3 M. Mixtures of benzophenone with hexachloro-p-xylene exhibit powerful synergism for photopolymerising styrene30 while an a-hydroxyketone system has been described which is not only a powerful initiator but also gives little odour31. Phenothiazine initiators have been found to graft onto the polymerising chains32,33 as did the use of TEMPO to provide stable polymeric radicals34. The use of 4-[diphenyl(trimethylsilyl)methyl]benzophenone also gives rise to grafted polymers with two types of silyl moieties35. At low initiator concentration a living polymer was obtained. Carbonate radicals generated by light from sodium carbonate have been found to successfully polymerise pyrrole36 while in polar media the application of a magnetic eld has been found to inuence the molecular weight and yield of poly(methyl methacrylate)37. Phenylazotriphenylmethane gives trityl radicals on irradiation formed by electron transfer38 that are apparently capable of inducing the polymerisation of cyclohexene oxide. Dye aggregation inuences the photoinitiation activity of Rose Bengal39 while morpholine-sulfur dioxide40 and bromine41 complexes initiate the photopolymerisation of methyl methacrylate. Camphorquinone is claimed to photoinduce the ring opening polymerisation of 4-methylenedioxolanes42 while carbocyanine borate salts induce photopolymerisation via an electron-transfer step43. Irradiation of polybutadiene with o-tolualdehyde has been shown to produce random copolymers44 whereas
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Photochemistry
xanthates induce the photopolymerisation of methyl methacrylate to give polymers with a narrow polydispersity45. The polydispersity was found to be independent of initiator concentration and the polymer chains were found to be capped with reactive `macroiniferters'. Oligooxypropylene-p-(benzoyl)benzoyl chloride copolymers with benzophenone end groups have been synthesised46 as have photoredox systems based on N-(4-benzoylphenyl)itaconimide and N,N-dimethylaminoethyl methacrylate47. The latter is claimed to be a powerful photointiator system that also grafts into the polymer chains. Macroazo initiators have been found to induce short chain photopolymerised fragments when compared to an equivalent thermally induced polymerisation48 while correlations have been established between the photochemical activity and electronic structure of aromatic azides49. Polystyrenes with a narrow molecular weight distribution have been made using a surfactant photointiator based on [4-(4'-tert-butyldioxycarbonylbenzoyl)benzyl]trimethyl ammonium chloride50. Here initiation occurs at the interface with the latex via the perester radicals. Pyridinium chlorochromate forms a complex with vinyl monomers51 giving free radicals on irradiation which induces vinyl monomer polymerisation with non-ideal kinetics. Titanocene is also an effective photointiator in visible light52 whereas ruthenium complexes give low yields of polymer at low pH53. Tetrahydrofurfuryl acrylate monomer has been photopolymerised using butyltriphenylborates as initiators54. Aromatic carbonyl initiators were found to act as effective sensitisers via an electron-transfer process with the borates. Iodonium butyltriphenylborate salts have been found to be more effective visible photointiators than the corresponding tetraphenylborate salt55. Bis(cyclopentadienyl)titanium dichloride has been found to give poly(methyl methacrylate) on irradiation with mixed solubility characteristics56 while organocobaloximes give rise to living polymers with different end functionalities57 having star or block architectures. Attempts have been made to identify the nature of the active species formed in metathesis polymerisation using tungsten hexacarbonyl58. Some studies have appeared on photoiniferters. Tetraphenylbiphosphine has been used as a photoiniferter with methyl methacrylate monomer59 where termination still occurred through the diphenylphosphine radicals. Benzyl phenyl selenide induces the photopolymerisation of styrene giving a and o chain ends60 while with methyl methacrylate the use of a piperidino-dithiocarbamate iniferter with a disulde transfer agent increased the living character of the growing chains61. Block copolymers of epichlorohydrin with styrene and methyl methacrylate have also been made using HBF4 as the initiator and N,N-di-ethyldithiocarbamate as the terminator62. A polymer with thiuram disulde end groups was obtained. Some aspects of the photopolymerisation kinetics of different monomers have been investigated. The photopolymerisation rate of methyl methacrylate is accelerated in the presence of oxygen when triethylamine is present63,64. This enhanced rate is associated with the usual oxygen-amine complex which can form a variety of species such as oxygen radical anions or hydrogen peroxide to give reactive hydroxyl radicals. The rate of photopolymerisation of methyl
339
methacrylate has been controlled using N-cetylpyridinium thiocyanate to give only oligomers65 whereas with furfuryl methacrylate degradation chain transfer has been observed via the furan ring66. Here activation energies were found to be higher where allylic radicals were concerned. Free radical propagation rate constants have been measured for different cycloalkyl methacrylate monomers67. The lowest rate using a pulsed laser system was observed for isobornyl methacrylate. A suitable procedure has been developed that allows calculation of the chain length distributions of polymers prepared by periodic modulation of the initiation process taking into account concomitant continuous initiation68. During the laser pulse the contribution from thermally induced reactions was found to be minimal at peak chain length distributions. In related work pulsed lasers have been used to ascertain the chain length dependence of the termination rate during styrene polymerisation69. Microscopic ows of liquid polymer during laser exposures have also been measured70 as have the growth of spherical polymeric microparticles71. Various new monomers include those for space applications72, photonic crystals73, suspension grade C6074, monlayers of azobenzene on 10,12-pentacosadiyonic acid75 and multimonomers of poly(acryloyloxyethyl methacrylate) and poly(methacryloyloxyethyl methacrylate)76. Polymers of a-methoxy-3,6endomethylene-1,2,3,6-tetrahydrophthaloyl-5-uorouracil have been found to exhibit anti-cancer activities77. Radicals produced in the solid state photopolymerisation of octadecyl sorbate are long-lived due to the production of allyl radicals78. In the solid state 5,4 structures only were obtained whereas in chloroform both 5,4 and 5,2 structures were produced. Fumarate esters with abstractable hydrogen atoms have been found to copolymerise on irradiation in presence of electron donor monomers79. Mixtures with N-vinyl formamide had higher exotherms than those with N-vinylpyrrolideone and vinyl ethers. In the photocopolymerisation of maleimides with vinyl ethers electron transfer occurs to give both cis and trans conformers80. Triplet states have been identied via laser ash photolysis for N-maleimides81,82. The same workers have also shown that planar N-arylmaleimides are ineffective initiators compared to ortho substituted twisted structures83. N-Substituted maleimides have also been found to form highly effective complexes with thioxanthone and benzophenone initiators84. The properties of a number of novel polymers have been described including biodegradable polyanhydrides85, hyperbranched polyesters86, dimethacrylatesilicate composities for yarns87, thermally stable polydihydrofuranyl compounds88, light stabilised systems89, gold-polydiacetylene nanocomposities90, evolutive dissipative structures in polyacrylate lms91, and photopolymerised microspheres92. The cycloaddition of 2,3-dimethyl-1,3-butadiene (DMB) to acrylonitrile was found to be independent of an initiator93. A 1:1 adduct was obtained consisting mainly of cyclobutane moieties. The triplet state of the DMB is supposedly involved. Copolymers of furfuryl methacrylate and N,Ndimethylacrylamide have been made94 as have copolymers of methyl acrylate with vinyl acetate using an aniline-benzophenone initiator mixture95. The acetate groups were then subsequently hydrolysed to give a PMMA-vinyl
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Photochemistry
alcohol copolymer. The template polymerisation of methacrylic acid in the presence of poly(vinyl pyrrolidone) has been studied96 and bulk copolymers of acrylamide with maleic anhydride have been made using benzoyl peroxide as the initiator97. The copolymerisation rate in the latter case was found to increase with increasing acrylamide and benzoyl peroxide concentration. Cationic photoinduced polymerisation continues to attract some interest. The oxidative quenching of a pyrrole-substituted ruthenium complex by a diazonium salt results in the formation of a metallopolymer98. Electron transfer within the complex oxidises the pyrrole moieties. Two novel a-terpineols have been photopolymerised via diaryliodonium salts99 as has 2,7dioxabicyclo[3.2.1]octane via N-ethoxy-2-picolinium hexauorophosphate100. The radical reaction of trimethylphosphite with 4,4'-di-tert-butyldiphenyliodonium hexauorophosphate gives trimethoxyphosphonium cations that can bring about the polymerisation of vinyl ethers101. Phenothiazine with antimony hexauoride anions is highly effective for the polymerisation of cyclohexene oxide101. The photobleaching of the salt was a good indicator of the polymerisation rate. The inuence of the counterion type has been examined on the initiation activity of diphenylamine diazonium salts102,103 and polyacrylamide has been prepared via a methylene blue/sodium toluene sulfonate/diphenyl-iodonium chloride complex104. An electron-transfer reaction between an excited uorane leuco dye and a diaryliodonium salt resulted in the formation of a ring-opening colourant to give active radicals capable of inducing the polymerisation of epoxy acrylate monomers105. Colour formation was a good measure of the conversion rate. A linear relationship was found between the conversion rate and Mn for the cationic induced polymerisation of THF by iodonium salts106. This reaction produced a living polymer that could add further monomer units such as N-2-(hydroxyethyl)ethylenmeimine. In the presence of 1,2-ethandiol the cationic polymerisation of 1,2-epoxy-6-(9carbazolyl)-4-oxahexane proceeds via the activated monomer mechanism107. Acylferrocene derivatives induce the photopolymerisation of ethyl-2-cyanoacrylate108,109, butyl glycidyl ether110 and cyclohexene oxide111. The latter workers have also found that the reaction promotes the activity of organic peroxides112. Styryl dyes with dimethylphenylacylsulfonium butyltriphenyl borate form donor-acceptor complexes that induce the visible laser photopolymerisation of acrylate monomers113. Crystal violet lactone undergoes a ring opening reaction to form the coloured cation in the presence of a phenyliodonium salt114. The reaction is induced by the acid release mechanism which breaks the lactone ring. Butenyl and pentenyl ethers have also been cationically photopolymerised115 while the anionic polymerisation of butyl acrylate has been undertaken with phosphazine base116. 2.2 Photocrosslinking A number of novel initiator systems/packages have been developed for photocuring. The vapour deposition of p-benzoquinone onto o-acryloylacetophenone oxime-styrene copolymers induced crosslinking117 while a covalent type microgel has been formed by treating a divinylbenzene-dimethylaminomethylstyrene-styrene copolymer with 3-chloro-
341
2-hydroxypropyl methacrylate and methacryloxyethyl sulfonate118. Microgels having a high number of cation groups on the particle surface showed high sensitivity due to the formation of exciplexes with the amino groups. Covalent type microgels were also found to be more reactive than ionic types. Photoinitiators have also been successfully grafted onto resin structures in order to minimise volatility and migration119 while the photolysis of acyloxyimino groups pendant in a styrene copolymer gives rise to amino capped chains120. An a-hydroxyketone photointiator, Esacure KIP 150, has been found to give no volatile aldehyde photoproducts after curing121. Monoacylphosphine oxide initiators have been found highly effective for initiating the photocuring of pigmented coatings122,123. A range of novel amine co-synergists have been made with poly(ethyleneoxy) groups124 with high reactivity and low extractability. Amine complexes with p-nitroaniline125 and ruthenium bipyridyl complexes126 have also been reported. In the latter case the rate of photopolymerisation is independent of initiator concentration and only participates in the actual initiation step. a-Alkylaminoacetophenone initiators have been found to be highly effective for photocuring pigmented inks when used with a longer wavelength absorbing initiator of the same structure127. Apparently, the hydrogen atom abstracting photoinitiators were not complementary. Copolymers with epoxy and oxime urethane groups have been synthesised128 that can cure through the evolution of photogenerated amines. This has interesting possibilities but may not be acceptable from a commercial point-ofview in terms of toxicity. Polymers bearing imino sulfonate groups generate acid upon irradiation that causes crosslinking129 and again, in a similar way, some borate esters have been made that release amine on irradiation130. Poly(3- and 4-vinylphenyl selenocyanates) have been synthesised and found to undergo crosslinking upon 254 nm irradiation131. Diphenyldiselenide was the main photoproduct along with phenylseleno and cyano radicals formed from the SeCN groups. Fullerene C60 has been used to polycondense furan132 rings that are attached to a methacrylate backbone. The light absorbing characteristics of tetraphenylborates have been enhanced through the substitution of chromophoric groups133. Cationic photocuring has also attracted interest. For cyclic enol ethers substitution of an a-methyl moiety enhances reactivity while methyl groups in b positions decreases it134. The addition of triethylene glycol divinyl ether has been found to enhance the reactivity of epoxy resin curing with an iron-arene complex135 while the crosslinking of disiloxanes via iodonium salts is dependent upon the media and sensitiser structure136. Crotyl glycidyl ether undergoes a regioselective cationic ring opening polymerisation to give a polyether137 and epoxidised castor oils have been found by the same group to form excellent low cost resins for cationic photocuring138,139. Epoxy functionalised polyisoprene has been crosslinked via cationic intiation140. Vinyl ethers were found to accelerate the process with inter and intramolecular interactions taking place. Polyepoxyacrylates have also been prepared via cationic photocuring with triphenylsulfonium141 and iodonium142 salts. Dihydrofuran and pyrans have also been photocured using iodonium salts143. Low conversions
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Photochemistry
were observed at rst that slowly increased in the dark due to the presence of living polymer. New cationic initiators for silicone release coatings have been prepared by reacting diaryliodonium salts with lithium tetrakis(pentauorophenyl)borate144. They induce fast cure for paper coating productions. Diazonium resins form complexes with sodium dodecyl sulfate and retain their high photointiation activity for coatings145. Diphenylamine aryl cations have been found to be the dominant intiation species in the photocuring of a condensate formed from a diphenylamine-4-diazonium salt and paraformaldehyde146. 3-Methoxydiphenylamine-4-diazonium salts have also been prepared and their activity examined in diazo resins147. Solid state photocuring and (2+2) cycloaddition processes have important applications in resist technologies. Hydropolysilanes have been made where the aryl derivatives undergo slower photobleaching than the corresponding alkyl derivatives148. For different functionalities photobleaching rates were found to be in the order p-cyanophenol > p-chlorocinnamic acid > pnitrophenol. Muconic acid derivatives on irradiation in the solid state gave essentially the (E,E)-isomers or tritactic polymers while ammonium derivatives were found to have very high photoreactivity149. Phthalimido chalcones undergo a (2+2) cycloaddition150 while in mixtures of poly(vinyl cinnamate) with poly(vinyl phenol) it has been possible to measure the separate types of non-bonded and hydrogen bonded double bonds151. Crosslink distribution in poly(vinyl cinnamate) has been examined152 while functionalised vinyl cinnamate monomers have been prepared with hydroxyethyl acrylate groups153. The anisotropic photo-orientation behaviour of poly(vinyl cinnamate) derivatives are inuenced by the chemical nature of substitutents at the ends of the side chains154. On the other hand the face to face stacking interactions between phenyl and peruorophenyl groups in (2+2) cycloaddition reactions is emerging as a common noncovalent interaction155. Changes in surface morphology have been determined in the (2+2) cycloaddition of poly(vinyl-4-methoxy cinnamate)156. The method of preparation controls the size of di-Et-(Z,Z)muconate crystals157 while crystal-crystal interactions have been observed in the polymerisation of bis(benzylammonium muconate)158. The solid state polymerisation of the dimethyl ester of p-phenylenediacrylic acid is heterogeneous and does not form a solid solution159 and various (2+2) cycloaddition reactions have been discussed160. Photocrosslinking of solid thermoplastics is also a subject of some interest. Blends of poly(2-chlorostyrene) and poly(vinyl methyl ether) have been successfully crosslinked through the photodimerisation of anthracene moieties labelled on the polymer chains161. It was found that the reaction kinetics approximate to the mean eld kinetics inside the spinoidal region, resembling the behaviour of the crosslink-reaction performed in the miscible region at relatively low crosslink densities. EPDM has been photocrosslinked using buckminsterfullerenes162 as has PVC using a triacrylate resin and diphenylketone photoinitiator163. Remaining with PVC, the chlorine atoms have been partially replaced with dithiocarbamate groups that undergo photocrosslinking in order to reduce the migration effect of
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the plasticisers164. Poly(ethylene oxide)has been photocrosslinked using a tetraalkylammonium salt165 and a triacrylate/benzophenone mixture166. Polystyrene with pendant benzoyl groups undergoes photocrosslinking to give resins with variable porosities dependent upon their concentration167. Photocrosslinked polyethylene becomes severely oxidised on the near surface layers168. Photocuring to produce enhanced property requirements for polymers and coatings is a wide topic of interest. These include bre-reinforced composities and laminates169 171, photomoulding of polyesters172, abrasion resistant polyester acrylates173, enhanced poly(vinyl alcohol) resists174, degradable networks175, production of nanoparts176, composite membranes177 179, microparticle encapsulation180, polyelectrolytes181, hot melts182 and optical lters183. Several studies have appeared dealing with polyimide systems. These include uorine containing derivatives184 186, polysiloxane derivatives187, chalcone derivatives188 and resist sensitivity189 191. Electro-optical devices have been made through doping of coatings192 as have self-assembled diazo resins193. A novel thermal curing reaction has been found for use in photogeneration of free amines, thiols and imidazoles194 as have novel isomerisable 4-vinylphenyl cyanates195. A number of studies have dealt with the properties of resins during and after photocuring for multifunctional methacrylates196 199, epoxy resins200, polyfunctional urethanes201,202, crown ethers203, styrene-maleic anhydride204 and polyesters205. Conductive studies have been undertaken on poly(vinyl ketones)206 and curing studies undertaken on pigmented systems207 and water based coatings208. Amphiphilic diblock copolymers of poly(vinyl alcohol) have been made209 as have cyclised isoprene rubbers with acid labelled tert-butyl carbonate groups210 for negative resists. Silicone polymers have also been made with vinyl211 and carbinol212 terminal groups and phenyldiacrylate derivatives213. The latter exhibit microphase separation of the siloxane and organic phases. Other studies include diacetyleneic-thiol monolayers214, tri-n-butylstannyl methacrylate-allyl chloroacetate copolymers215 and acylphosphine oxides for inorganic pigmented coatings216. Monitoring cure kinetics continues to attract much interest. Fluorescence ranks high on the list for monitoring the cure rates and appears to be growing in interest. Such studies include stilbene, oxazolyl and biphenyl molecules in methyl methacrylate217, pyrenetetrasulfonic acid for microemulsion polymerised polyacrlaonitrile218, pyrene for cyclohexylmethacrylate219, phenyl glyoxylate for diacrylate monomers220,221, phenanthroline organometallic complexes in epoxy acrylates222, phenoxazone in vinyl esters223, Schiff bases in epoxy resins224 and organometallic complexes in aromatic cyanate esters225,226. Other related methods include charge-recombination luminescence227, pigmented inks228, bre optic methods229,230 and general curing apsects231,232. The kinetics of di- and tetra-functional monomers have been studied and postpolymerisation radicals monitored via ESR233 235. The functionality of the resin had a major controlling inuence in the nature of the termination reactions. Dielectric loss has also been found to be a useful measure of cure
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Photochemistry
kinetics236 indicating that the morphology of the resin is a function of light intensity. The kinetics of the 3-dimensional photopolymerisation of dimethacrylate monomers is described237 and different monofunctional monomers give rise to different kinetic responses238. No double gel effects have been observed in the copolymerisation of acrylate and dimethacrylate monomers239 while monomers with several double bonds give heterogeneous networks240. Kinetic cure models have also been developed for dimethacrylate monomers in dental curing241 and stereolithography242. Methods of photocuring are variable. The photocuring of acrylates has been monitored by photoDSC in the presence of alumina suspensions243. Apparently, the ller has no effect on the rate. Of particular interest is the attempt to photopolymerise 4-vinylbenzoate and p-phenylenediacrylates in hydrotalcite interlayers244. Whilst the 4-vinylbenzoate photodimerised to give the polymer the 4-phenylenediacrylates gave only oligomers. The state of aggregation of the monomers in the pores was dependent upon the anion charge in the clay. Monolayers of octadecyl acrylate give stereoregular material on irradiation245 and UV curable composities have been found to be as tough as equivalent thermally cured systems246. The photomoulding of resins is not without problems in terms of release247 as are hot melt adhesives248. Conductivity methods have been found useful for measuring the photocuring of resins249 while ion mobility spectrometry has been found useful for measuring extractable components in UV cured coatings250. Deep photocuring in lled composities has been overcome251 as have temperature variations during cure252. Carboxylate counterion interactions have been monitored in diacetylene carboxylate monolayers via reective infrared spectroscopy253. In the presence of certain divalent ions the coordination mode changes from a bridging state to a bidentate state. Standards in rates of UV polymerisations have been assessed by using visible laser systems with little success254. Hydrogen sesquioxane has been rendered photopatternable by spinning onto glass surfaces255 and ring opening mechanisms for epoxypolyamides have been examined by FT NMR256. Ink curing processes have also been monitored257. The photopolymerisation of liquid crystals is attracting signicant interest. The liquid crystal phase and the temperature have been found to markedly inuence the photopolymerisation kinetics if acrylate monomers258. For ferroelectric liquid crystal possessing a chiral moiety polymerisation has been found to be highest in the smectic phase in the absence of an applied external electric eld259. Thus, in the initial polymerisation stages molecular alignment was more important whereas during the later stages diffusion rates dominated. The application of an electric eld immobilised the smectic phase. Similar studies have been undertaken on reverse mode polymer stabilised cholesteric textures260. The photopolymerisation of triphenylene acrylates in the mesophase has been found to be inuenced by small amounts of residual initiator261. Defect sites are created reducing the carrier mobility by one order of magnitude. Divinyl ether networks have also been prepared by cationic polymerisation262 while the retention of molecular orientation during curing
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of liquid crystalline systems is crucial for the optimisation of anisotropic mechanical and physical properties263. The solid state polymerisation of diethyl cis,cis-muconate gave crystals, the size of which depended upon the molecular weight of the polymer264. A model has been developed to dene growing spherulites during the irradiation of polymer dispersed liquid crystals265. Under intense UV liquid crystal droplets are formed while under low intensity irradiation the growth of spherulites occurs in a circular shape to give 3D plates. A nematic liquid crystal has been made with a high birefringence from mercapto and olenic compounds266, while large amounts of a liquid crystalline polymer have been found to reduce the photopolymerisation rate of a mixture of a divinyl ether and a bismaleimide267. Benzanthrone derivatives have been utilised as luminophores for liquid crystals268 whereas the pretilt angle of photoreactive polymers is inuenced by exposure to polarised light269. Second order non-linear optical activity has been observed in photocrosslinked polymers of glycidyl methacrylate with 4-nitro-4'-hydroxy stilbene270. The anisotropic properties of discotic liquid crystals are stabilised by in-situ photopolymerisation271. However, using X-ray diffraction studies diacrylate systems showed a decrease in order with increasing polymerisation temperature. Similar studies have been undertaken on difunctional reactive Schiff bases whereas Cu(II) ions inhibited their polymerisation272,273. Photocrosslinkable polymers have been developed based on cinnamoylethoxybiphenyl where anisotropy increases with increasing irradiation temperature274 276. Intramolecular photoreactions dominated at the smectic temperature. Other work on biphenyl containing polymers has developed phase diagrams for the various transitions277 whereas cholesteric polyesters based on cinnamic acid undergo (2+2) cycloaddition causing stabilisation of Grandjean textures278. 2.3 Photografting The photografting of monomers onto polymer substrates continues to attract interest for property modications. A review using Ce(IV) ions has appeared279 while the hydrophilicity of polysulfone membranes has been enhanced through photografting of poly(ethylene glycol) with 4-azidobenzoyl-methoxy groups280. Polyacrylonitrile has also been successfully photografted onto poly(sulfopropyl acrylate)281. Reactive maleic anhydride sites have been photografted onto both polypropylene powder282 and polystyrene surfaces283. For polyolens successful photografting has been performed with methyl methacrylate vapour284, hydroxypropyl acrylate285 and acrylamide286. Poly(N-isopropylacrylamide) has been photografted onto poly(vinyl alcohol)287 while acrylonitrile has been photografted onto starch288. A new process of photografting has been developed through dentritic polyesters289 while cellulosics have been photografted with N-isopropylacrylamide290 and 4-vinylpyridine and iso-butyl methacrylate291. Polyester bres have been photografted with acrylic acid292 whereas Fe-Si bonds have been grafted onto oligoorganosiloxanes293. N-Isopropylacrylamide has been photografted onto glass294 and acrylic acid onto PTFE to improve adhesion295,296.
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Luminescence and Optical Properties
The eld of polymer luminescence and general optical properties continues to grow at an alarming rate. Signicant interest centres on polymers for LED applications and photochromic materials. This last year has seen an exponential growth in papers in both areas with much emphasis on the poly(phenylene vinylenes) for LEDs. A number of specic and general reviews of interest have appeared. Topics of interest include conjugated polynitriles297, polymer blends298, interfacial membranes299, memory effects in polymers300, dentrimers301, chemical sensors302, femtosecond studies303, rare earth polymers304, chemiluminescence of elastomers305, `glo polymers'306, photoprobes for microstructural analysis307, polymer degradation308,309 and chemiluminescence for monitoring degradation310,311. A general review312 has appeared while another author questions whether or nor `polarons' exist313. Three reviews have appeared on isomerism with azo polymers314 316 while others show that luminescence is a valuable tool for monitoring the molecular behaviour of polymers317,318. Several reviews have appeared on LED conjugated polymers319 324. Chemiluminescence analysis continues to attract much interest in the eld especially with regard to polymer oxidation processes. Studies on polyamides have shown that the chemiluminescence source is primarly associated with cyclic hydrogen bonded lactam hydroperoxide with the o-aldehyde of the amide325 while thermoluminescence has associated the emission with electron detrapping and recombination processes326. Imaging chemiluminescence continues to be reported as a valuable method for examining the hetergeneous oxidation of polymers such as rubbers327. Other workers have clearly shown the usefulness of the methods for monitoring the performance of stabilised polymers328. Here it has been found that the migration of the stabilisers inuences the chemiluminescence intensity. For lled rubber a direct correlation has been found between DSC analysis and chemiluminescence329. The chemiluminescence of different polyolens has been related to the methyl group content330. One can assume that this relates to the ability of reactive hydroxyl radicals to abstract labile tertiary hydrogen atoms generating more hydroperoxides in the polymers. In g-irradiated polymer the chemiluminescence is associated with free hydroperoxides331 while in another study various additives were found to prevent the g dose effects332. Other studies on polyolens include kinetic irregularities333 and combined stress334. The use of chemiluminescence for monitoring the stability of coatings is not yet viable although can be used to screen clear coats335. In polysilanes the electroluminescence is associated with energy transfer and carrier generation processes336,337 while other studies has dealt with the chemiluminescence of wood338, polymeric uorophores339 and free radical measurements340. In terms of general polymer luminescence there have been a number of novel reports. Colour contaminants have been identied in the manufacture of terephthalic acid as a precursor to polyester341. Using uorescence analysis the primary contaminant formed by oxidation was 4-carboxybenzaldehyde. This
347
product gives rise to biphenyl, uorenone and anthraquinone products on further degradation. The luminescence from chitosan is associated with an intramolecular hydrogen bond342 while photostimulated emission from poly(methyl methacrylate) is dependent upon chain mobility343. Mirror imaged uorescence is associated with the rod like structure of polysiloxanes344 while a tetraphenylsilane polymer is signicantly more uorescent than a hexaphenyl structure345. Fluorescent plasma polymers have been made from aromatic hydrocarbons346 as have uorescent poly(aryl ether ketones)347, aromatic polyamides348, oligomeric esters of 3-thienylglutaric acid349 and polysulfones350. The uorescence from wood and paper pulps is complex. Thus, whilst the emission from solid wood is independent of excitation wavelength, extracts show a dependence indicating the presence of many, possibly hidden components351. Fluorescence is also claimed to be useful in identifying the pulp source352 354 while uorescence from biphenyl components has been found to be highly dependent upon the torsional angle of the molecules in the pulp355. Polysiloxane lms give yellow luminescence, the intensity of which is dependent upon the energy uences of He, C or Au ions356. For a series of diethynyl-2,2'-bipyridineRe(CO)3CI polymers the uorescence has been found to decrease with increasing Re content along the chain357. It is possible that the Re atoms are acting as exciton traps. A novel electron transporting polymer has been synthesised from mesitylene borane and 1,9-dicyanoanthracene358. The polycyclodiborazane emits strongly at 494 nm and is highly thermally stable. The plasma induced luminescence from polypropylene is found to be dependent upon its crystallinity359 while the electroluminescence for crosslinked polyethylene is dependent upon its state of degradation360. Photochromic polymers have seen a major growth especially those based on azobenzene and spyropyran chromophores. New photochromic polymers have been developed based on the spyropyran unit with polymerisable groups361. The groups were found to be sensitive to the heterogeneity of the polymer and had potential for the development of optical storage information media. Metal ions bound to photochromic naphthoxazines gave highly uorescent species362 while the presence of zinc 1-hydroxy-2-naphthoate has been found to markedly improve the lightfastness of spyropyrans363. Azobenzene bound to poly(methyl methacrylate) (PMMA) exhibited gas permeation changes when light switched from the trans to the cis form364 while solvent dilation changes have been similarly observed in azo tagged poly(vinyl alcohol)365. Polyacetylene derivatives with phenylazo groups exhibit smectic liquid crystalline properties366 while photoinduced alignment in azobenzene-methacrylate copolymers decreased with increasing367 strength of donor-acceptor groups attached to the 4,4' positions of the azo chromophore. This was associated with the higher enthalpic stability of the mesophase and the decreased concentration of cis-azo groups. The ferroelectricity of surface stabilised aligned lms of photochromic azo-benzene polysiloxanes is reversible on UV/visible light irradiation368. Polarised absorption spectroscopy indicates that this light switching controls the degree of order, orientation and EZ photoisomerism of the chains. Chiral
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Photochemistry
inductions have been reversed in isocyanate-azo polymers369,370 and optical switching in vinyl copolymers with crowned azobenzene groups has been found to induce changes in ionic conductivity371. Ionene polysoaps bearing azobenzene groups can be optically switched to adsorb polyelectrolytes at different layers372 while cationic stilbene amphiphiles can be optically switched to control microviscosity effects373. Copolymers with polar ester and azobenzene groups can be switched to control birefringence374,375 while orientation effects in Langmiur-Blodgett lms of azobenzene tagged polyamic acids have been studied via second harmonic generation376. The time dependence of photoinduced isomerism in azobenzene doped PMMA has been monitored via real time infrared377 whereas a novel palladium catalysed homocoupling process has been developed for preparing azocoulped polymer materials378. Strongly visible absorbing naphthopyrans have been developed379 along with copolymers with diphenylthiocarbazonylmercury groups380, bis-spiropyrans via ultrasound381, poly(2-methyl-oxazoline)382, polymers of azobenzene and cholesterol383,384, photochromic bres385, crown ether styryl dyes386, amphiphilic phenylazonaphthalenes387, azobenzene PMMA systems388, bis-spironaphthoxazines389, dithienylethene pendant polyacrylics390, polypropylacridine spyropyrans392, poly(S)-4-(2-methacryloyloxyviologens391, 393 propanoyloxy)azobenzene and spyran doped PMMA394. A general overview on many types of structures has also been presented395. Cis-trans isomerism in polyamides provides information on molecular constraints396,397 while photomechanical motions have been measured in azo doped poly(vinyl alcohol) lms at air-water interfaces398. A mean eld model of photoinduced surface reliefs in dye substituted polymers has been developed399 as has the dynamic properties in azo doped acrylics for optical storage data400. Urethane substituted diacetylene lms have been grown onto Ag lms and found to exhibit a dielectric constant comparable to those of orientated lms401. Polyesters with norbonadiene units have been made and found to undergo highly efcent photosensitised transformations yielding large amounts of thermal energy402. Azobenzene-succinimide polymers on the other hand gave rise to optical birefringence403 whereas photochromic hybrid organic-inorganic materials have been developed that undergo marked changes in refractive index404. Poly(aryl ether ketones) have been made with azobenzene groups and the cistrans isomerism dependence on molecular weight measured405. Spyropyrans have been grafted onto PMMA and found to exhibit useful solvent permeation effects on isomerism406. Polymers with benzylidenephthalimidine side chains undergo (2+2) cycloaddition407 while the cis-trans isomerism of Disperse Red 1 dye doped in PMMA can be tted to the time dependence of the macroscopic chain dynamics408. A stochastic model has been developed for azo side chain polymers409 and random association processes have been measured in polymers with spirobenzopyran molecules410. Here an increase in solvent quality or screening by co-ions suppresses photoassociation. A common feature in this process was the formation of large clusters with short irradiation times followed by a plateau when the photostationary state is achieved. The kinetics of cluster dissolution were, in fact, found to be twice as slow as the relaxation
349
time of the spontaneous photochromic conversion of the spyropyran moieties. Spiroindolinonaphthaloxazine groups have been incorporated into ormocer groups via the sol-gel route and found to be relatively thermally stable411 while 2-phenylphenanthroimidazole dimers exhibit piezochromic behaviour412. Following on from this there are numerous related articles on liquid crystalline materials with a major review on optical storage media413. Poly(Nvinylcarbazole) doped with amino-dicyanostyrene is a high performance photorefractive polymer414 as are functionalised acrylate composities with 1,4,:5,8-naphthalenediimide groups415. Photopolymerisation of this medium creates an anisotropic gel like material in which the liquid crystal is free to reorientate in the presence of a space-charge eld. Transient periodic stripe domains have been observed in copolymer vesicles416 and the effect of various dyes examined on the properties of liquid crystalline materials for colouration purposes417. The uorescence dynamics of cyanobiphenyl in a liquid crystalline composite has been examined418. Here surface excitation was undertaken at 266 nm while bulk excitation was performed at 320 nm. In the former case short-lived excimers were formed while in the bulk long-lived excimers dominated the decay prole due to nematic molecular associations. Fluorescence shifts have also been monitored from polyesters containing 4,4'-biphenyldicarboxylate moieties419. Various uorescence patterns are observed during the heating cycles. Fluorescence analysis has also been used to examine the aggregates in rod-like polyesters420 formed from pyromellitic anhydride and 4,4'-biphenyl units. Ground-state charge-transfer complexes are formed between both moieties having an alternating lateral alignment inside a layer. Two layered crystals are seen with different lateral packing distances which are shown to match exactly the electron-donating and electron-accepting units in the adjacent chains. It is suggested that these types of charge-transfer interactions contribute to the organisation of the spatial arrangements of the different phase structures. Metal(II) p-styryl octadecanoates have been found to form an inverted hexagonal lyotropic phase at ambient temperature with the exception of Cu(II) ions421. Photochemical crosslinking of these monomers gives rise to polymer networks with phase retention. Photoinduced `command' effects have been designed as a new method for the development of planar or homeotropic alignment of photochromic polymers422 and three types of uorescence emission have been observed from substituted benzanilides in the crystalline state associated with different states423. The level of photoinduced LC alignment in polymethacrylates with benzylidenephthalimidine side chains has been found to be enhanced by p-methoxy substitution at the benzylidene residue424. With these polymers photodimerisation under controlled polarised light irradiation markedly enhanced the thermal stability of the LC alignment due to the formation of the crosslinks. Diethyl (Z,Z)-2,4-hexadienedioate undergoes polymerisation to give a high molecular weight, highly stereoregular polymer425 while poly(vinyluorocinnamate) undergoes liquid crystal alignment perpendicular to the direction of polarisation426. Several cholesteric polysiloxanes have been synthesised that can be racemised427,428 as have smectic diacrylates429, thiophenes430 and poly(2,5-didecyloxy-1,4-phenylenebu-
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Photochemistry
tadiynylene)431. Several azo polymers have also been made with liquid crystalline textures. These include polymethacrylates with p-nitroazobenzene groups432 435 as well as azobenzene groups436 441 and 1,4-butanediol diacrylate-4-(2-acryloyloxyethoxy)azobenzene copolymers442. The technique of time resolved photomodulation has been used to examine the excitation dynamics in luminescent Si-bridged polythiophene443 as has the luminescence in cyclosiloxanes444. Electropolymerised indole monomers gives a cyclic trimer polymer445 with long wavelength shifted uorescence while polyimides give excimer uorescence due to head-to-tail intermolecular overlap446,447. Ground state complexes were also observed due to various packing conformations. The application of an electric eld has been found to decrease the luminescence from polymer blends448. This is due to intra- and intermolecular dissociation processes. Quantum mechanical calculations have been used to investigate the inuence of interchain interactions on the absorption and emission spectra of p-conjugated systems449. These data have enabled guidelines to be established in terms of maximising the parameters that control the luminescence intensity from solid lms. Electronic relaxation processes in polydiacetylenes have been found to be sensitive to changes in chain conformation450 whereas 3D photoplasticity studies have been undertaken on polycarbonate451. Lasing action in conducting polymers has been examined452 while UV induced changes have been examined in poly(pyridinium salts)453. Articles dealing with LED polymers based on poly(p-phenylene vinylene) (PPV) have grown exponentially in the last year. Polymer modication has been undertaken through various routes in order to enhance the LED properties in relation to the emission quantum efciencies, electrical conductivity and photoconductivity. PPV with peruoro groups exhibit maximum emission in the blue region454 while uorinated oligomers of PPV exhibit a reduced emission efciency with increasing solvent polarity455. PPV with aromatic amine groups exhibit red-orange uorescence456 while material with sulnyl oxidation centres have restricted conjugation but increased emission intensity457. Alternating poly[(p-phenyleneethynylene)-alt-(2,5-thienyleneethynylene)] has been made and found to exhibit uorescence quantum yields of between 0.40.5 with relatively good solvent solubility458 as have polymers with 2,6-pyridylene groups459 for green and blue emission. Cyano substituted PPVs gave emissions that are dependent upon the excitation wavelength460 whereas polymers of 2,2'-bipyridine and phenyldiacetylene have an emission quantum yield of close to unity461. PPV with in-chain and pendant 9,10diphenylanthracene groups have been synthesised and found to exhibit combinations of spectra in electro and photoluminescence that are dependent upon the nature of the chromophore462. For example, PPV with in-chain and pendant chromophores exhibited electroluminescence only from the in-chain chromophores whereas the uorescence originated from the pendant groups. Blue emission has been observed from silicon containing PPVs463 while PPVs with diphenyl substitution are more stable since these groups act as conjugation breaks464. Dioctyloxy and didodecyl-PPVs exhibit aggregates and reduced
351
emission intensities465,466 while a number of soluble phenylate PPV's have been made that emit strong green emission467. Polymers with 2,5-dialkoxy groups have also been made and exhibit strong emissions468,469 while alkylated products are reported to give an emission intensity of 65%470. The alkyl chain length has an important bearing here471 with non-aromatic substitutions giving polymers with blue shifted emission spectra472. PPV has been prepared by CVD473 and has also been examined by ultrafast spectroscopic techniques474 478 including time-of-ight474 for carrier mobility, picosecond laser ash photolysis475 to determine the excitation intensity dependence of the emission, femtosecond spectroscopy to measure excited state dynamics476,477 and the use of PPV's themselves as polymer laser diodes478,479. The prospects for producing electric pumped solid-state polymer diode lasers using PPVs is discussed in the context of low-threshold gain narrowing in sub-micron thick lms. Structural effects on luminescence efciency are important. Apparently, an increase in the exible components in the PPV chain enhances the uorescence efciency480 while two annihilation processes have been identied that hamper the emission481. Electron withdrawing substitutents apparently reduce the uorescence482 of PPV's whereas fast uorescence decays are observed at high excitation densities which apparently disappear at low uences483. Here dipoledipole interactions between spatially extended photoexcitations is suggested as a mechanism for the observed bimolecular decay. Liquid crystalline PPV's exhibit uorescence with a dependency on chain length484 as do phenylene polymers under pressure485. Vinylene bonds also inuence the oscillator strengths in PPV's486 while blends of PPV with a red emitter poly(perylene-codiethynylbenzene) undergo effective energy transfer processes487. Triplet state efciency can be examined by time-resolved thermal lensing488 while a general strategy has been developed for the construction of ordered nanaocomposities with hexagonal symmetry using polymerisable lyotropic liquid crystals489. Using ion-exchange procedures amphiphilic polymers are obtained with signicantly different emissions from that of bulk PPV. Poly(1-phenyl-1butene) has been found to be more emissive than poly(phenylacetylene)490 whereas the emission from PPV is signicantly reduced on photodegradation491. Dopants also inuence the emission processes from PPVs. Improved red dopants have been based on pyran dyes492 while C60 doping appears to be variable493 496. Doping with electron transport materials such as oxadiazoles give polymers with balanced properties for hole transport497. The avoidance of low molecular weight material in the synthesis of cyano based PPVs is important498 as are head to head and tail to tail chain sequences in thiophene based polymers499. Head to tail tetramer sequences were the most uorescent. Metal ion doped PPV's are claimed to be good chemosensors500 and broad emission is observed from titania doped PPV501. Electron rich dopants enhance the emission in the red region502 while electro and photoinduced infrared bands from PPV are similar503. Electric eld induced uorescence quenching on a series of poly(p-terpheny-
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Photochemistry
lene vinylenes) follows a strictly quadratic dependence on the applied eld amplitude504. Here quenching occurs predominantly at higher emission energies, causing a distinct blue shift between the electro modulated and photoinduced spectra. In a pair of coupled donor-acceptor conjugated polymer chains it is possible for an exciton which is photoexcited on either polymer to decay into a hole in the donor polymer's valence band and an electron in the conduction band of the acceptor polymer505. A processable PPV has been developed via m-phenylene units506. Here the chains are able to adopt a coil like conformation. Unfortunately, a second emissive band is observed in the red region. Photochemically converted PPV has been characterised507 while those with biphenyl units are stacked and exhibit LC properties508. Head-totail sequences in poly[(p-phenylene ethynylene)-alt-(2,5-thienylene ethynylene) give rise to enhanced uorescence509 as do alkoxysulfonated PPVs which can be self-assembled into LED's510. A number of other LED polymers have been made such as poly(1,4naphthalene vinylenes)511, polymers with 2-benzylidene-4,5-dicyano-1,3dithiole512, coordinate silicon units513, poly(alkylphenylacetylene)514 all exhibiting strong green emission. Poly(benzimidazole-4,7-diyl)s are highly electroluminescent but also exhibit electrochromism515. Fluorene is a strong excimer quencher516 in LEDs while poly(p-pyridine)517, poly(4,4'-biphenylene pyromellitimide)518, arylethylene disylylene polymers519, polymers of distyrylbenzene520, polyamides from tetra(4-biphenylyl)-4,4''''-diamino-pquinquephenyl521 and poly(cyanoterephthalylidene)522 exhibit strong blue emissions. Polymers with boron atoms are highly rigid structures with an intense blue emission523 as are those based on poly(amic acids)524. There has also been a surge of interest in thiophene polymers. Dual luminescence from polythiophene lms has been assigned to exciton trapping at different local environments525 while binaphthyl526 and oxadiazol527,528 thiophenes exhibit a variety of coloured emissions. Poly(alkyl esters) exhibit orange emission529 while tetra and sexithiophenes exhibit blue emission530. The kinetics of luminescence decay in hexamethylsexithiophenes are controlled by excess energy redistributions via vibrational and torsional coupling531,532. Polythiophenes with aniline units exhibit high electrical conductivity533 while quinquethiophenes exhibit long-lived emissions due to aggregates and physical defects534. In poor solvents the emission characteristics of poly(3-hexylthiophene) are similar to those of the solid lm535. Silylene polymers also exhibit dual emissions536 whereas poly(dialkylthiophenes) with 4,4'-dicarboxylate groups exhibit chain twisting with an orange uorescence emission and red electroluminescence537. Relaxation processes have been examined in transpolyacetylene538 540 showing that relaxation processes are twice as fast as charge-transfer. High excitation energies also gave rise to the formation of neutral long-lived states absorption edge excitation leading to a higher probability of chain relaxation into a deformationally neutral state with a long lifetime. Polymer blend studies have attracted much less interest. Strong excimer formation in blends of polystyrene with 1,4-bis(4-a-cyano-styryl)-2,5-dio-
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ctyloxybenzene correlates with enhanced photoconductivity541 whereas morphological changes during the phase separation of polyamide/polysulfone blends are effectively measured via a uorene probe542. Excimer uorescence can also be used to measure miscibility in polyolen/polymethacrylic acid blends543. Shear force microscopy can also measure topographical differences between blends of conjugated polymers544 while photoisomerism has been used via trans-stilbene moieties for blends of polystyrene-vinyl methyl ether545. In the latter case variations in reaction and annealing rates results in elastic stress caused by reaction inhomogeneities which play a role in the formation of lamellar like morphology. Polystyrene size is measured in blends of polystyrene and poly(vinyl methyl ether) using co-2-vinylnaphthalene probes546 while for blends of poly(vinyl alcohol) with poly(vinyl acetate) phase separation via uorescence microscopy was evident by the use of anthracene and uorescein547. Here the rich poly(vinyl alcohol) phase was evident through green uorescein emission while for the poly(vinyl acetate) the blue anthracene emission dominated. Polyamic acid and polyimide mixtures are monitored via perylenetetracarboxydiimide uorescence548. The aromatic amide groups in the polyamic acid were found to function as quenchers. A few articles have appeared dealing with dendrimers. A four generation dendrimer has been made with a rubicene moiety549 that contains two emitting conformations. Here dentrons close to the core exhibit a different decay process to that on the outer sphere. Dendrimers with a crown ether receptor moiety and a hydrophobic dentritic sector can be optically switched via a photoresponsive azobenzene group550. Electron-transfer quenching in dendritic macromolecules has been found to exhibit an unusually large quenching constant with DABCO551. Here ground-state charge-transfer complexes and exciplexes were formed with the higher generation dendrimers. Dendrimers with a calix[4]arene core and azobenzene skeletons has been synthesised552 as have dendrimers with central azobenzene linkers553,554. Metallic based dendrimers have also been synthesised as multielectronic catalysts555. Energy transfer and excimer formation continue to attract widespread interest in terms of molecular dynamics. The mobility in polystyrene-poly (ethylene glycol) microbeads has been ascertained through a pyrenebutyric acid probe556. Excimer to monomer intensity ratios were found to be in accordance with the solvation capacity of a liquid phase. Only in the solid dry beads is aggregated excimer emission observed. The addition of anionic surfactants has been found to control the interpolymer aggregation in naphthalene labelled styrene/N,N-dimethyl maleimido propylammonium sulfate copolymer557. The pH induced expansion of polyacrylic acid labelled with pyrene and naphthalene has been followed by a reduction in excimer formation558. The energy transfer distance between the chromophores also increases. Poly(n-vinylcarbazole) and its copolymers exhibit two types of traps559. The rst is associated with a conventional sandwich structure of overlapping aromatic rings while the second type is due to species involving two partially overlapped carbazole substituents. In the copolymer intermolecular interactions are high even when the carbazole content is low. At low
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Photochemistry
temperatures the contribution from the second type of trap increases. Implicit in this work is the nding that the high concentration of excimer forming traps mitigates against signicant energy migration between the carbazole groups which might otherwise populate the excimer traps. In free radical polymerisation the rate of photoelectron transfer has been found to be much lower than the rate of diffusion controlled processes560. Thus, for processes controlled by diffusion, the reactivity of free radicals formed as a result of electron transfer limits the rate of initiation. For a series of vinyloxy polymers and copolymers with benzonitrile groups substitution with electron rich groups caused signicant quenching561 563. Spectral broadening was also caused by interaction chromophores whereas isolation on the chain resulted in spectral narrowing. Mixed systems of polyhexyl and diphenylsilanes exhibit intermolecular energy transfer the efciency of which is dependent upon the mixing ratio564,565. Complex triplet energy migration has been observed in methacrylate copolymers with 9-phenanthryl groups566 as have relaxation processes in benzophenone doped polystyrene567. No evidence for excimer formation has been found in carbazole containing oligomeric ethers568. Intramolecular energy migration was shown to occur in these systems but trapping was inefcient. Interfacial interactions at blends of latexes have been monitored through the use of donor-acceptor chromophores569. Here interfacial contact and surface area controlled the efciency of the energy transfer process. The presence of a surfactant reduced the energy transfer by increasing the interfacial barrier. The presence of pendant benzophenone groups enhances the isomerism of norbornadiene groups tagged to epoxy resins570 while hole recombination at dimeric sites gives delayed exterplex emission in perylene doped polystyrene571. Polyelectrolyte chemistry and micellar interactions continue to attract widespread interest. The dynamic anisotropy of Sulforhodamine 101 at a water/ phthalate ester interface has been found to be restricted to the X-Y plane572. This was explained in terms of different adsorption modes of the dye on the interface and the chemical structure of the ester. In ethylene-methacrylic acid ionomers using pyrene as a hydrophobic probe the critical micelle concentration (CMC) was determined to be 0.02% w/w573. Below the CMC unimeric micelles were identied that are in equilibrium with the larger aggregates. For a naphthalene tagged copolymer of poly(dimethyl sulfate acrylamide/N,Ndimethylaminopropylmaleimide) the hydrodynamic diameters were found to decrease with increasing salt concentration due to chain coiling574. Enhanced compartmentalisation of the naphthalene labels were observed at high salt concentrations. Fluorescence decay proles have been generated by the Monte-Carlo technique during the interdiffusion of donor-acceptor spheres for mimicking latex lm formation575. Microdomains in amphiphilic monomers of N,N-diallyl-N,N-dialkylammonium chloride have been found to be ordered576 while non-radiative energy transfer from naphthalene to pyrene groups has been found useful for detecting hydrophobic associations in copolymers of sodium 2-(acrylamido)-2-methylpropanesulfonate and N-dodecylmethacrylamide577. Discrepancies between different techniques for measuring CMCs
355
have been ascertained578 while in methyl methacrylate-methacrylic acid fractions with vinylanthracene groups Ca(II) and Tb(III) ions have been found to bind strongly and enhance the uorescence of the chromophore579. An ethylene oxide-propylene oxide-ethylene oxide triblock copolymer does not micellize at concentrations below 5% w/w580 whereas amphiphilic cationic porphyrins are stabilised by polyallylamine at pH values close to the pKa of the amine581. Dansyl labelled polyanions exhibited a high response to alkali metal cations582 while photoassisted poling and depoling has been measured in biaryl tagged zwitterion polymers583. The viscoelasticity of micellar cetyltrimethylammonium bromide is reduced by the addition of ionene polyelectrolytes due to the shortening of the worm like micelles584. Excitation energy migration in micellar pores has been modelled585 and amphiphilic ruthenium(II) polypyridine complexes have been investigated on interfacial surfaces586. Microviscosity effects in Naon-Na+ membranes have been measured through pyrene probes587 indicating that the probes themselves are located at the uorocarbon/water interface. Hydrophobic microdomains have been measured in modied polyelectrolytes588 592, vinyl polymer latexes593, cetyl pyridinium chloride with metal complexes of 8-hydroxyquinoline-5-sulfonic acid594 poly(dimethylamino)alkyl methacrylate-block-sodium methacrylate595, poly(benzyl glutamate)/poly(ethylene oxide) copolymers596, azo initiated poly(dodecyltrimethylammonium bromide598, methyl methacrylate)597, 599 poly(ethylene-co-methacrylate) and non-ionic cellulose derivatives600. In the latter case, using pyrene and perylene probes, microviscosity effects were dependent upon the CMC with increasing polymer hydrophobicity giving rise to an increase in the rigidity of the polymer-surfactant aggregates. The nanosecond dynamics of molecular complexes have been discussed in depth601 while J-aggregates in dyes have been examined by pressure dependent absorption and uorescence measurements602. Other studies on polymer labelling include the use of pyrene labelling for methyl methacrylate latexes where the excimer emission is related to annealing effects603. The polymerisation rate of hydroxyethyl methacrylate has been measured in the presence of triethylamine and excited pyrenebutyltrimethylammonium ions604. Electron transfer was found to be highly dependent upon the nature of solvent used in the polymerisation process. In the case of pyrene labelled poly(ethylenimine) excimer emission increases with decreasing pH due to chain coiling605. The absorption and uorescence characteristics of perylene tagged poly(ethylene oxide) have been found to be independent of the polymer chain length in dilute solution606 whereas the uorescence of a new Schiff base of o-phenylenediimidocellulose is highly dependent upon pH607,608. Fluorescent probes have been found useful for the determination of the functionalisation of atactic polypropylene609 while C60 has been covalently linked to alkylsulfonate groups610. The relaxation time of anthryl groups on a poly(ethylene oxide) (PEO) chain increases with increasing chain length611 up to a maximum of 4000. The PEO chain has a much higher local mobility than vinyl polymers such as styrene. The uorescence properties of dialkylamino modied polysiloxanes depended upon the crosslink density612 whereas the
356
Photochemistry
uorescence of poly(N-isopropylacrylamide) shows that the polymer undergoes a conformational transition from a exible coil to a globular structure, followed by collapse to give aggregates613. The uorescence from porphyrin tagged methacrylate copolymers decreases with increasing porphyrin groups614 while the same chromophore exhibits marked changes in absorption when polymerised into poly(N-isopropylacrylamide)615. Polymer doping experiments continue for various applications with emphasis on dye chromophores. Tetraphenylporphene has been used as a dissolved oxygen sensor in plastic bres616 while the uorescence quenching of 1,2benzanthracene in poly(vinylbutyral) has been described by a fractal cluster model617. Coumarin 6 has been observed to form aggregates and is also highly sensitive to the pH of the environment618. This molecule was able to detect Lewis acidity in certain types of zeolite that were otherwise thought to be nonacidic. The kappa number in single wood bres has been measured using Acridine Orange as a molecular probe619 while acridine has been found to be a useful molecular probe in polyamines620. Using 9,10-diphenylanthracene as a molecular probe in PMMA the effective thickness of a degradation front is greater and radical propagation rate slower in glassy polymers621. Benzonitrile derivatives have been used as molecular weight detectors622, static quenching observed in polysilanes623, molecular alignments determined in PMMA624 626, colourants determined in Japanese woodblock prints627 and the association of uorocarbons measured in poly(N-isopropylacrylamide)628. Dimethylketene has been identied as the photoluminescence precursor in plasma polymerised lms of methyl methacrylate with tetramethyl-1,3-cyclobutanedione629. Rhodamine 6G in PMMA changes from isolated dye molecules to nanocrystallites at high concentrations on plasma irradiation630. Rhodamine B in poly(acrylic acid)631 and benzylidenemalonitriles in PMMA632 exhibit pressure sensitive uorescence while Rhodamine 6G has been found useful for measuring spherical polymer particles633. Temperature proles are claimed to be measured during processing634 as are melting and crystallisation processes in pyrene doped polyethylene635. Dyes which have geometrical asymmetry in their molecular structure are useful for anisotropy measurements636. A novel route has been developed to tunable emission in smart gels637 while chitosan self-association has been monitored through a avone molecular probe638. Rhodamine B has different conformers when grafted to cellulose639 while 9-methylanthracene is an effective dye for monitoring internal stresses in coatings640. The reaction kinetics of 9-hydroxymethyl-10-[9-(naphthyl methoxy)methyl]anthracene reects the rearrangements of local free volume in PMMA641 whereas surface concentrations of rhodamine 6G have been measured on derivatised silica642. Fluorescence studies show that divinylbenzenestyrene gels continue to grow after gellation643 while the presence of metal ions interfere with the measurement of dyes on bres644. Dyes based on pyrene and perylene has measured temperature proling in the curing of resins645 as have scalar behaviour in bulk uids646. The compound 1,1-dicyano-4-(4'-dimethylaminophenyl)-1,3-butadiene is a valuable rotor for polymers647. Gellation effects in PMMA were easily monitored. The botanical source of amylose can
357
be measured by tagging the sugar with 2-aminopyridine648 and N-phenyl-Nnaphthylamines can measure probe depths in poly(N-isopropylacrylamide)649. The local dynamics in heterogeneous polymerisations have been measured using pyrene probes where termination was noted by an enhanced excimer emission650. Perester initiators, however, were powerful quenchers. Pyrene has also been used to measure gellations in methcarylate polymers651,652, cholesterol-methacrylates653, and polybutadienes654. Micrometric measurements have been undertaken on labelled polysiloxanes cast onto steel surfaces655, charge-transfer processes in amino-substituted boron dipyrromethane dyes656, dimethylaminophenylphenanthrene probes in thermosensitive N-isopropylacrylamide657 and polyelectrolyte behaviour using fullerene probes658. Rare earth complexes have been investigated in some depth. The electrochemical redox processes for europium complexes can be switched in PEO giving rise to different types of uorescence659. Europium complexes with polyacrylic acid are different when compared to those in copolymers660,661 and cellulose662 where the uorescence is higher. Europium(III) ions form complexes with CMCs, the uorescence intensity of which is higher in the solid state than in solution663. Europium naphthoate complexes give intense red emission in polystyrene664 and highly conductive uorescent metal-porphyrazines have been made665. Strong uorescence has been observed from Tb(III) complexes in poly(N-oxides)666 as do samarium complexes in PMMA667. Europium ternary complexes have also been made with triphenylarsine and triphenylstilbene668 and photochemically induced charge separation has been electrostatically constructed in organic-inorganic multilayer composities669. Silver ion complexes have been observed in ethanol following g-irradiation670 while alkyl substituted porphyrin polymers are useful optical sensors671. Tb salicylate complexes exhibit strong uorescence in PMMA672 while the time resolved emission from polypyridylruthenium derivatised polystyrene is dependent upon the Ru(II) content673. 4 Photodegradation and Photooxidation Processes in Polymers
The photooxidation and photodegradation of polymers continues to attract some interest but is not as widespread as in previous years. Review articles have appeared dealing with poly(2,6-dimethyl-1,4-phenylene oxides)674, photocatalyst bres675, polymers with azo links676 and accelerated weathering specications677. Other articles of interest include the design of an integrating sphere for repeatability in polymer ageing678 and the use of FTIR for monitoring the photostability of clearcoats679. 4.1 Polyolens An Arrhenius model has been developed for lifetime prediction of the light stability of polypropylene680. Photooxidation processes in blends of polypropylene with poly(butylene terephthalate) (PBT) are complicated by the thermal sensitivity of the polypropylene and the screening effect of the terephthalate ester681. This effect is shown in Scheme 1.
358
h
Photochemistry
*
PP/PBT
O C O
C O O PBT
(CH2)4
with
O C O
C O O
(CH2)4
O C O (CH2)4 2
IR absorbing end-groups + O Me CH2 C H PP

hydrogen abstraction
Coloured conjugated structures
CH2
CH (CH2)3
O2, PH
O C O CH (CH2)3 OOH
Me CH2 C CH2
PH O2
O C
HO O O CH (CH2)3
Oxidation products of PBT
Me CH2 C CH2
inhibited reaction
OOH
Accumulation of hydroperoxides
Oxidation products of PP
Scheme 1 Photooxidation mechanism for PP/PBT polymers
Conjugated chromophores develop from the PBT and these will screen the photoinduced decomposition of the hydroperoxides in PP. This effect results in an accumulation of hydroperoxides from the PP. Iron diethyldithiocarbamate has been shown to exhibit an initial stabilisation effect on polyethylene followed by sensitisation682 as does anthraquinone683,684. Trace volatiles have been measured during the photooxidation of polyethylenes685 while ferric stearate/cerium(III) mixtures686 and starch materials are good degradants687. 4.2 Poly(vinyl halides) Photodehydrochlorination occurs in PVC with a foam backing688 as determined by Raman spectroscopy. For PVC stabilised with Zn/Ca stearates phooxidation indicates that dehydrochlorination dominates over oxidation at the inner layers beyond 100 microns689 692. The effect of polyene formation also appears to be a function of light intensity as well as oxygen diffusion rate.
359
4.3 Poly(acrylates) and (alkyl acrylates) Fluorinated acrylics are inherently photostable693 while the vacuum UV photolysis of PMMA results in de-esterication and double bond formation694. The stereostructure of PMMA also has an important inuence on the product distribution695. X-Ray and UV exposure of PMMA was ngerprinted via FT NMR analysis696. 4.4 Polyamides and Polyimides The photodegradation of a polyamidehydroxyurethane is dependent upon the light ux697 and is sensitised by the addition of Fe3+ ions698 and riboavine699. The latter indicated the possible role of singlet oxygen in the photooxidation although this was not substantiated. Carbonyl and hydroxyl products have been monitored in the photooxidation of nylon 6,6700 and dye xation is reduced701. Fractal kinetics have also been applied to the photooxidation of polyamides702,703 allowing an estimation of homogeneous and non-homogeneous factors. 4.5 Poly(alkyl and aromatic ethers) Using laser ash photolysis poly(2,6dimethyl-1,4-phenylene oxide) undergoes scission at the phenolic link to give phenoxy radicals704. Poly(vinyl methyl ether) has been shown to undergo a complex series of photoprocesses as shown in Scheme 2.705
H CH2 C OMe OOH CH2 C OMe 3290 cm1
h,
h, O2
Autoxidation
OH R + CH C OMe 1650 cm1 (trans) 1670 cm1 (cis) O CH2 C CH2

1
O
RH
CH2 C OMe 3440 cm1
CH2 C OMe + OH
CH2 +
O CH2 C OMe 1737 cm1

O2, RH
H2O
1718 cm + OMe
O
C
CH2 + CH2
CH2 OH 3440 cm1
CH2 OOH 3290

+ RH
+ R
cm1
h,
RH
CH2 O O + R C OH + OH
MeOH
1707 cm1 1754 cm1 Scheme 2 Photooxidation mechanism of PVME
360
Photochemistry
The major product is the ketodiester with methanol as a major volatile. The photoyellowing is associated with polyconjugation formed via the dehydration of hemiacetals. 4.6 Silicone Polymers Laser ash photolysis of poly(methylphenylsilylene) gives a transient absorption associated with exciton states706 while fullerene reduces bond scission in polysilanes707. 4.7 Polystyrenes and Copolymers Rates of singlet oxygen reactions in polystyrene have been examined by time resolved spectroscopy708. Solute diffusion coefcients were considered to have an important inuence on the rate constants and these, in turn, varied with the type of reactant. Irradiation of styrene-butadiene-styrene block copolymer gave alcohols and epoxides as products which were not observed to be formed in high impact polystyrene709. The presence of sulfur dioxide and nitrogen dioxide signicantly accelerate the photodegradation of polystyrene710 while ESR has identied the formation of allyl and alkyl radicals711. The photodissociation of peroxide in polystyrene is primarily associated with the evolution of water and CO2712. 4.8 Polyurethanes and Rubbers The photooxidation of polyether-polyurethanes exhibits sensitivity due to the ether segments713. Formates were the primary products of photorearrangement. The addition of styrene-butadiene copolymers to polyolens signicantly enhances their susceptibility to photooxidation via the butadiene component714. Horizontal attenuated FTIR spectroscopy has been found useful for detecting the products of photooxidation of rubbers715. 4.9 Polyesters Aliphatic polyesters undergo rapid outdoor degradation and are claimed to be viable as environmentally friendly716. The photodegradation of polyester coatings has been investigated in depth717 while for poly(butylene succinate) depth proling on photooxidation to 312 nm irradiation showed a gradual decrease in chromophore concentration whereas for poly(ethylene terephthalate) chromophore development did not go beyond 10 microns718. 4.10 Photoablation of Polymers Laser ablation remains a topical subject. Phenylhydrazine has been found useful in aiding the excimer ablation of PTFE719 as are bithiophene compounds720. An anomalous increase in the spectral diffusion of hole burning in PMMA samples has been observed when doped with Zn tetrabenzoporphyrin721 while large and small changes in microenvironments have been noted when hole burning PMMA and polyethylene722. Excimer laser ablation of polysilane lms has been successfully carried out723 as has PTFE using amine based charge-transfer complexes724. The photochemical hole burning in poly(vinyl alcohol) gave more stable holes when doping with unimolecular micelles than with tetraphenyl-
361
porphyrine725 while polymers with photolabile azo links undergo microexplosions on laser ablation726. Vacuum UV excimer laser ablation of a uorinated polymer lm gave good wettability727 whereas a polyurethane lm has been ablated in the presence of a polysaccharide for hydrophilic packaging applications728. 4.11 Natural Polymers Amino acids are shown to participate in the photoinduced oxidation of silk with protein yellowing being inhibited by the presence of a UV absorber729,730. Monomeric o-quinones are considered to be the major chromophores responsible for the photoyellowing of paper pulps731. In another study, the formation of p-stilbene-phenols are found to be the major yellowing chromophores732. In sapwood various resinols have been identied and formed via quinonemethide intermediates733. Transient radicals produced from a-guaiacoxy-b-propioveratrone are intermediates in lignin photoyellowing734 and these have been monitored via ESR735. The colour changes in softwoods have been monitored736 while the production of peroxyformic processes in the production of pulps has been improved737 and their effects examined on photoyellowing738,739. Phenoxy radicals have been measured in situ on paper following laser ash photolysis740 and biotreatment of spent liquors examined for bleaching741. The photoinduced formation of enzymic polymers produced from coniferyl alcohol form large assemblies called `supermodules'742. Other studies include the photodegradation of populus grandis743, thiol stabilisation of hardwood744 and photodegradation of milled wood lignin745. Using Raman spectroscopy the rate of S-S cysteine bond scissions can be monitored in wool bre746. 4.12 Miscellaneous Polymers The photooxidation of an epoxy cured resin increases through the layer at a constant rate747 while photobiodegradable starches have been synthesised by grafting vinyl ketone monomers748. Vinyl ketone copolymers give vinyl end groups and crosslinking on irradiation749. A new method has been developed for monitoring the out-door ageing of dispersed coatings750 and anhydride cured epoxy resins have been monitored via FTIR analysis751. Iron doped poly(ethylene-co-acrylic acid) acts as a sensitiser752 while the decay of radicals has been measured in PMMA glasses753. Bivoltine silk bres undergo an initial process of chain scission followed by extensive crosslinking on irradiation754. The photoyellowing of coatings has been measured755 as has the photodegradation of clear coats756 and polymer metal complexes757. The bio and photodegradation rates of poly(hydroxybutyrate-co-hydroxyvalerate) have been measured and controlled758 as have organotin macromolecules759. Poly(alkylaryldiazosuldes) undergo photorearrangement from the E to the Z form760 while thermal blankets have been made for spacecraft from a peruoropropylene-tetrauoroethylene copolymer761. Using laser desorption mass spectrometry triterpenes undergo polymerisation762. Polyperoxides degrade energetically763 while the photodegradation of a 4'-nitrostilbene polymer is highly wavelength dependent764. New ndings into the yellowing of coatings have been made765 and the
362
Photochemistry
water barrier of paints examined by FTIR766. Polydiacetylene undergoes random chain scission followed by depolymerisation on irradiation767 whereas polyanhydrides undergo rapid crosslinking768. Polyphenylene ether only undergoes surface degradation protecting its bulk through self screening769 while the incorporation of side groups into PPV's enhances their photolytic stability770. Nitro groups have been found to be particularly effective in this regard. Chain scission reactions in different acrylic melamine clearcoats have been examined771 as have photoreactions in peruorinated polymers772 and nanosized polyacrylates773. 5 Photostabilisation of Polymers
A number of reviews on polymer photostabilisation have appeared774 780 as well as the stabilisation of ceramic paints781, clearcoats782, wood nishes783 and car body paints784 786. Hindered piperidine stabilisers (HALS) have also been reviewed in depth787 and the surface stabilisation of polystyrene covered788. The dielectric strength of polyethylene has been measured as a function of additive concentration789 while in stabilised polymers the depth of degradation was found to be uniform790. HALS have been found to be effective stabilisers for UV cured coatings and do not inuence the cure rate791. Bleached wood pulps can be effectively stabilised by ascorbic acid792 and wool by hydroxybenzotriazoles and HALS793. Hydroxybenzotriazole stabilisers also protect wood pulp794 and polyurethanes by co-reaction795. The spectroscopic properties of monomeric and polymeric benzotriazoles have also been compared796. UV absorbers are effective in clear coats797 and when grafted to wood798. Dihydroxybenzophenone stabilisers inhibit the chain scission in the photodegradation of poly(methoxyacrylophenone)799 while tin stabilisers have also been found to photostabilise PVC800. Several studies have dealt with HALS stabilisers. A number of novel naphthyl and naphthoate-HALS derivatives have been synthesised and evaluated as thermal and light stabilisers in polyolens801. The naphthalene moiety is found to induce good thermal and light stability with the tertiary structures operating more effectively in the latter case. In another study it was found that naphthalene adducts with HALS are less effective as stabilisers802. Polymer bound HALS have been found to be more effective than either the monomeric or polymeric types in stabilisation803. The g-ray grafting of HALS to polyolens gives rise to improved performance804 as did partially grafted HALS to polyurethanes805. Polymeric HALS are also effective when grafted into PMMA806 and other polymers807,808 as well as when doped into polysiloxanes809. The time evolution of nitroxyl radicals produced in the photo-oxidation of polypropylene has been monitored via ESR810. The migration of HALS during irradiation has been shown to be effective only when oxidation products in the polymer build-up to an effective concentration811.
363
Photochemistry of Dyed and Pigmented Polymers
A review has appeared on the photodegradation of dyes812 and another article on carbon black technology813. Of particular interest is the observation that zinc 1-hydroxy-2-naphthoate photoprotects photochromic dyes814 as does a UV absorber for azo dyed silk815. Benzanthrone dyes enhance the photostability of PMMA816 and testing methods for colour fastness have been assessed for some reactive dyes817. Enzymatic processes for the degradation of dyes have been examined818 while diffuse reectance spectroscopy is useful for examining the triplet states of dyes in situ on polymer fabrics819. Singlet oxygen has been found to be dynamically quenched on cotton bres. The photofading of reactive azo dyes in various bound and unbound forms has been assessed. Dyes with the reactive substituent were more photostable while a methoxy substituent reduced stability820. Covalently xed dyes were also more photostable to perspiration effects821,822. The addition of uorescent brightening agents alters the hue of dyes after washing823 whereas the presence of ferric citrate reduces dye lightfastness824. Photobleaching processes for uorescent rhodamine dyes have been examined under conditions where a two step photolysis is involved825 while methylene blue undergoes photochemical reduction with an amine826. The light stability of triarytlmethane dyes is reduced when bound to bovine albumin and this correlates with an enhanced uorescence quantum yield827. Using ESR dichlorouorescein is shown to undergo a one electron transfer process to give a semiquinone radical that is immediately oxidised on admitting oxygen828. A rhodacyanine dye photofades via a self-sensitised reaction with singlet oxygen829 and photobleaching reactions have been examined for a uorescein dye in cotton830. Much of the work on pigments centres on titanium dioxide pigments. Calcium carbonate has been shown to behave as a stabiliser in polyethylene831. Titanium dioxide ller particles become agglomerated after photooxidation in PVC-rubber mixtures832 whereas in PVC itself titanium dioxide pigment induces subterranean polyene formation833. Stabiliser interactions have been studied with uncoated rutile and anatase pigments in the photooxidation of polypropylene834. Rutile is found to be synergistic with phenolic antioxidants and HALS but antagonistic with hydroxyaromatic absorbers. In the presence of anatase pigment strong antagonism is observed especially in the presence of mixtures of stabilisers. Polymeric HALS are found to perform well against the photocatalytic effect of the anatase pigment. Microwave dielectric spectroscopy has been developed to describe the charge-carrier dynamics in titanium dioxide pigments835. Shifts in the resonant frequency and microwave power are related to the population of free carriers and photocatalytic activity of the pigment. Photoinduced electron transfer from bound anthracene carboxylic acid dye to titanium dioxide (titania) nano-particles depends upon the synthetic method for the particles836. Facile electron transfer was observed for the anatase modication. Apparently, silica alone on the surface of titania particles gives poor coatability whereas mixtures with alumina are superior837. The
364
Photochemistry
surface activity of nanoparticulate anatase was blocked to reduce its activity for acrylic paints838. Degradation processes in PTFE depend on the nucleating efciency of the titania particles839. Wood pulps are effectively bleached using titania pigments840 while carboxylic acid formation has been found to be high in titania lled rubber and atactic polypropylene841. Titania lms have been sputtered onto the surface of polyester lms842 and found to photocatalyse the decomposition of azo dyes843 845 in solution and cotton846. Encapsulating titania particles in crosslinked polymers reduces their photoactivity847. 7
1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15. 16. 17. 18. 19. 20. 21. 22. 23. 24. 25. 26.
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Vol 31 Photochemistry

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Contents

6 Advances in Instrument Design and Utilization

Chapter 1 Photolysis of Carbonyl Compounds By William M. Horspool

1 Norrish Type I Reactions

4 Photochemistry of Dienones 4.1 Cross-conjugated Dienones 4.2 Linearly Conjugated Dienones

93 93 95 96 96 99 100 101 103 104 104 104 106

134 137 137 138 140

145 145 154 163 165 171 175 176 182

References Chapter 5 Photo-reduction and -oxidation By Alan Cox

2 Reduction of the Carbonyl Group

Reduction of Nitrogen-containing Compounds Miscellaneous Reductions

202 205 209 21 1

8 Oxidation of Nitrogen-containing Compounds

220 225 226

Chapter 7 Photoelimination By Ian R Dunkin

303 304 307

309 312 3 14 314 314 317 3 19 321 322 324

Polyesters Photoablation of Polymers Natural Polymers Miscellaneous Polymers

6 Photochemistry of Dyed and Pigmented Polymers

References Author Index

Me CH2 CH2 N+ Me, Cl Me

Me C Me CH2 SO3, Na+

III: Polymer Photochemistry

III: Polymer Photochemistry

III: Polymer Photochemistry

III: Polymer Photochemistry

III: Polymer Photochemistry

Luminescence and Optical Properties

III: Polymer Photochemistry

III: Polymer Photochemistry

III: Polymer Photochemistry

III: Polymer Photochemistry

III: Polymer Photochemistry

III: Polymer Photochemistry

IR absorbing end-groups + O Me CH2 C H PP

Coloured conjugated structures

Oxidation products of PBT

Scheme 1 Photooxidation mechanism for PP/PBT polymers

III: Polymer Photochemistry

OH R + CH C OMe 1650 cm1 (trans) 1670 cm1 (cis) O CH2 C CH2

CH2 C OMe 3440 cm1

O CH2 C OMe 1737 cm1

CH2 OH 3440 cm1

CH2 OOH 3290

1707 cm1 1754 cm1 Scheme 2 Photooxidation mechanism of PVME

III: Polymer Photochemistry

III: Polymer Photochemistry

Photochemistry of Dyed and Pigmented Polymers

III: Polymer Photochemistry

III: Polymer Photochemistry

III: Polymer Photochemistry

III: Polymer Photochemistry

III: Polymer Photochemistry

III: Polymer Photochemistry

III: Polymer Photochemistry

III: Polymer Photochemistry

III: Polymer Photochemistry

III: Polymer Photochemistry 842. 843. 844. 845.

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