Dyes and Chromophores in Polymer Science

Jacques Lalevée, Institut de Science des Matériaux de Mulhouse, France. Jean Pierre Fouassier, ENSCMu-UHA, Mulhouse, France.

• Preface xiChapter 1 Trends in Dye Photosensitized Radical Polymerization Reactions 1Jacques Lalevée and Jean-Pierre Fouassier1.1 Introduction 11.2 A brief overview of dye-based PISs 61.2.1 Dye one-component systems 61.2.2 Dye two-component systems 71.2.3 Dye three-component systems 101.3 A discussion on specific or recent developments in dye-based photoinitiating systems 121.3.1 Dyes for use with polychromatic visible lights 141.3.2 Dyes for blue, green and red laser light-induced polymerizations 161.3.3 Dyes as part of PISs in the medical area 181.3.4 Dyes in controlled radical photopolymerization reactions 191.3.5 Photoinitiation under soft irradiation conditions: novel three-component systems 191.3.6 Dyes with red-shifted absorptions and high molar extinction coefficients 221.3.7 Performances of novel three-component PISs in low-viscosity matrices under LEDs/laser diodes  and low-intensity household devices 231.3.8 Recoverable dyes: the concept of photoinitiator catalysts 251.3.9 Metal-based dyes: recent perspectives 261.3.10 Dyes under sunlight exposure 271.3.11 Dye-based PISs as a source of mediator radicals: application to FRPCP 271.3.12 Dyes exhibiting a dual radical/cationic behavior: application to concomitant radical/cationic photopolymerizations 281.3.13 Dyes in thiol-ene photopolymerizations 291.3.14 Dyes for the manufacture of photopolymerizable panchromatic films 291.3.15 Dyes for polymerization of in situ nanoparticle containing films 301.4 Dye-based photoinitiating systems: properties, efficiency and reactivity 311.5 Trends and perspectives 321.6 Bibliography 34Chapter 2 Sensitization of Cationic Photopolymerizations 45James Crivello2.1 Introduction 452.2 Photosensitization of onium salts 482.3 Synthesis of long wavelength absorbing photoinitiators 502.4 Photosensitization of onium salt cationic photoinitiators 512.5 Early dye sensitization studies 552.6 Polynuclear aromatic hydrocarbons and their derivatives 562.7 Phenothiazine photosensitizers 602.8 Carbazole photosensitizers 622.9 Thioxanthone photosensitizers 632.10 Curcumin as a photosensitizer 642.11 Quinoxaline photosensitizers 652.12 Miscellaneous electron-transfer photosensitizers 662.13 Free-radical-promoted photosensitization 662.14 Conclusions 702.15 Bibliography 71Chapter 3 Controlled Photopolymerization And Novel Architectures 81Sean Doran, Omer Suat Taskin, Mehmet Atilla Tasdelen and Yusuf Yagci3.1 Introduction 813.2 Photoinitiated controlled radical polymerizations 843.2.1 Photoiniferter 843.2.2 Photoinitiated nitroxide-mediated radical polymerization 873.2.3 Photoinitiated atom transfer radical polymerization 893.2.4 Photoinitiated RAFT polymerization 973.3 Photoinitiated living ionic polymerization 1023.3.1 Living cationic photopolymerization 1023.3.2 Living anionic photopolymerization 1063.4 Acknowledgments 1083.5 Bibliography 109Chapter 4 Applied Photochemistry in Dental Materials: From Beginnings to State of the Art 123Joachim E. Klee, Maximilian Maier and Christoph P. Fik4.1 Photoinitiated free radical polymerization 1234.1.1 Introduction: from ultraviolet to visible light curing 1234.1.2 The camphorquinone/amine system 1244.1.3 Acyl phosphine oxides 1274.1.4 Various other photoinitiator systems 1294.2 Cationic photopolymerization 1334.3 Conclusion 1344.4 Bibliography 134Chapter 5 Photoinitiated Cross-linking in Oleds: An Efficient Tool for Addressing the Solution-processed Devices Elaboration and Stability Issues 139Frédéric Dumur and Didier Gigmes5.1 Introduction 1395.2 Cross-linking of light-emitting materials 1415.2.1 Polymer-based light-emitting materials 1415.2.2 Small-molecule-based light-emitting materials 1545.3 Cross-linking of charge-transport materials 1575.3.1 Polymer-based hole-transport materials 1575.3.2 Polymer-based electron-transport/injection materials 1655.3.3 Small-molecule-based hole-transport materials 1675.4 Conclusion 1695.5 Bibliography 170Chapter 6 Polymers as Light-harvesting Dyes In Dye-sensitized Solar Cells 183Thanh-Tuân Bui, Xavier Sallenave and Fabrice Goubard6.1 Introduction 1836.2 Characterization of DSSC devices 1856.3 Poly(3-thiophenylacetic acid)-based polymers 1886.4 Phenylenevinylene-based polymers 1946.5 Triphenylamine-based polymer 1956.6 Fluorene-based polymers 1966.7 Dye polymers with acceptor–donor structure 1976.8 Polymer containing metal complexes 1996.9 Conclusion 2056.10 Bibliography 206Chapter 7 Nir-dyes for Photopolymers and Laser Drying in The Graphic Industry 213Bernd Strehmel, Thomas Brömme, Christian Schmitz, Knut Reiner, Steffen Ernst and Dietmar Keil7.1 Introduction 2137.2 Computer to plate systems 2167.2.1 Technical remarks 2167.2.2 Photochemical aspects of photoinitiation using NIR lasers 2187.2.3 Importance of thermal deactivation 2307.2.4 Contrast materials and color on demand 2327.2.5 Sensitivity 2367.3 Laser-drying and offset-printing 2397.3.1 Principle of laser-drying 2397.3.2 Chemical systems 2417.4 Conclusions and outlook 2437.5 Acknowledgments 2447.6 Bibliography 244Chapter 8 Dyes and Photopolymers 251Yue Qi and John T. Sheridan8.1 Photopolymer 2518.2 Dye study of the photopolymer materials 2608.3 Conclusion 2718.4 Bibliography 272Chapter 9 Advanced Strategies for Spatially Resolved Surface Design Via Photochemical Methods 279Anja S. Goldmann, Guillaume Delaittre, Jan O. Mueller and Christopher Barner-Kowollik9.1 Introduction 2799.2 Inorganic surfaces 2829.3 Bio and bioinspired surfaces 2969.4 Cross-linking 3099.5 Conclusion 3149.6 Bibliography 315Chapter 10 Photosynthesized High-performance Biomaterials 327Julien Babinot, Estelle Renard, Valérie Langlois and Davy-Louis Versace10.1 Introduction 32710.2 Surface photografting methodology 32910.2.1 Photoinduced “grafting-from” method 32910.2.2 Benzophenone and derivatives 32910.2.3 Ketones and derivatives 33110.2.4 Photo-oxidation process 33310.2.5 Photoiniferters for living/controlled surface photografting 33410.2.6 Triarylsulfonium salts 33510.3 Photoinduced “grafting-to” procedure 33710.3.1 Aryl azides chemistry 33710.3.2 Anthraquinone-derived monomers 33710.4 Achievements and biomedical applications of the photosynthesized materials 33910.4.1 Achievements 33910.4.2 Stimuli-responsive materials 34110.4.3 Modification of membranes 34310.4.4 Biomedical applications 34410.4.5 Enzymes and proteins immobilization 34710.4.6 Cell adhesion and compatibility 34810.5 Conclusion 35010.6 Bibliography 350Chapter 11 Light-cured Luminescent Coatings for Photovoltaic Devices 361Federico Bella, Gianmarco Griffini, Roberta Bongiovanni and Stefano Turri11.1 Photovoltaics: technology, devices and spectral management 36111.1.1 Energy demand and photovoltaic converters 36111.1.2 Spectral management for photovoltaics: principles, materials and applications 36411.2 Photocurable luminescent downshifting layers and dye-sensitized solar cells 37111.3 Luminescent solar concentrators 37811.4 Bibliography 385Chapter 12 Polymers with Photoinduced Self-healing Properties 393Julien Poly12.1 Introduction 39312.2 Healing based on photo-reversible cycloadditions 39512.3 Healing based on photoinduced homolytic dissociations of covalent bonds 39912.4 Photoinduced healing in supramolecular polymers and related systems 40812.5 Healing based on photothermally induced phase transitions or photo-isomerizations 41312.6 Conclusion and perspectives 41612.7 Bibliography 418List of Authors 423Index 427