Dyes and Chromophores in Polymer Science E-Book
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- Herausgeber: John Wiley & Sons
- Kategorie: Fachliteratur
- Sprache: Englisch
The design and development of dyes and chromophores have recently attracted much attention in various research fields such as materials, radiation curing, (laser) imaging, optics, medicine, microelectronics, nanotechnology, etc.. In this book, the recent research for the use of dyes and chromophores in polymer science is presented. The interaction of the visible light with the dyes or the selected chromophores is particularly important in different fields (e.g. for photovoltaic, display applications (LED ...), laser imaging or laser direct writing, green chemistry with sunlight induced photopolymerization etc ...). This book gives an overview of the dyes and chromophores for all the important fields.
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Veröffentlichungsjahr: 2015
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Table of Contents
Cover
Title
Copyright
Preface
1: Trends in Dye Photosensitized Radical Polymerization Reactions
1.1. Introduction
1.2. A brief overview of dye-based PISs
1.3. A discussion on specific or recent developments in dye-based photoinitiating systems
1.4. Dye-based photoinitiating systems: properties, efficiency and reactivity
1.5. Trends and perspectives
1.6. Bibliography
2: Sensitization of Cationic Photopolymerizations
2.1. Introduction
2.2. Photosensitization of onium salts
2.3. Synthesis of long wavelength absorbing photoinitiators
2.4. Photosensitization of onium salt cationic photoinitiators
2.5. Early dye sensitization studies
2.6. Polynuclear aromatic hydrocarbons and their derivatives
2.7. Phenothiazine photosensitizers
2.8. Carbazole photosensitizers
2.9. Thioxanthone photosensitizers
2.10. Curcumin as a photosensitizer
2.11. Quinoxaline photosensitizers
2.12. Miscellaneous electron-transfer photosensitizers
2.13. Free-radical-promoted photosensitization
2.14. Conclusions
2.15. Bibliography
3: Controlled Photopolymerization and Novel Architectures
3.1. Introduction
3.2. Photoinitiated controlled radical polymerizations
3.3. Photoinitiated living ionic polymerization
3.4. Acknowledgments
3.5. Bibliography
4: Applied Photochemistry in Dental Materials: From Beginnings to State of the Art
4.1. Photoinitiated free radical polymerization
4.2. Cationic photopolymerization
4.3. Conclusion
4.4. Bibliography
5: Photoinitiated Cross-linking in OLEDs: An Efficient Tool for Addressing the Solution-Processed Devices Elaboration and Stability Issues1
5.1. Introduction
5.2. Cross-linking of light-emitting materials
5.3. Cross-linking of charge-transport materials
5.4. Conclusion
5.5. Bibliography
6: Polymers as Light-Harvesting Dyes in Dye-Sensitized Solar Cells
6.1. Introduction
6.2. Characterization of DSSC devices
6.3. Poly(3-thiophenylacetic acid)-based polymers
6.4. Phenylenevinylene-based polymers
6.5. Triphenylamine-based polymer
6.6. Fluorene-based polymers
6.7. Dye polymers with acceptor–donor structure
6.8. Polymer containing metal complexes
6.9. Conclusion
6.10. Bibliography
7: NIR-Dyes for Photopolymers and Laser Drying in the Graphic Industry
7.1. Introduction
7.2. Computer to plate systems
7.3. Laser-drying and offset-printing
7.4. Conclusions and outlook
7.5. Acknowledgments
7.6. Bibliography
8: Dyes and Photopolymers
8.1. Photopolymer
8.2. Dye study of the photopolymer materials
8.3. Conclusion
8.4. Bibliography
9: Advanced Strategies for Spatially Resolved Surface Design via Photochemical Methods
9.1. Introduction
9.2. Inorganic surfaces
9.3. Bio and bioinspired surfaces
9.4. Cross-linking
9.5. Conclusion
9.6. Bibliography
10: Photosynthesized High-Performance Biomaterials
10.1. Introduction
10.2. Surface photografting methodology
10.3. Photoinduced “grafting-to” procedure
10.4. Achievements and biomedical applications of the photosynthesized materials
10.5. Conclusion
10.6. Bibliography
11: Light-cured Luminescent Coatings for Photovoltaic Devices
11.1. Photovoltaics: technology, devices and spectral management
11.2. Photocurable luminescent downshifting layers and dye-sensitized solar cells
11.3. Luminescent solar concentrators
11.4. Bibliography
12: Polymers with Photoinduced Self-healing Properties
12.1. Introduction
12.2. Healing based on photo-reversible cycloadditions
12.3. Healing based on photoinduced homolytic dissociations of covalent bonds
12.4. Photoinduced healing in supramolecular polymers and related systems
12.5. Healing based on photothermally induced phase transitions or photo-isomerizations
12.6. Conclusion and perspectives
12.7. Bibliography
List of Authors
Index
End User License Agreement
List of Tables
6: Polymers as Light-Harvesting Dyes in Dye-Sensitized Solar Cells
Table 6.1. Physical, optical and photovoltaic characteristics of PTA1-12, PPV1-8, PTPA 1-3, PF1-6 and PAD1-6
Table 6.2. Physical, optical and photovoltaic characteristics of PMC1-25
7: NIR-Dyes for Photopolymers and Laser Drying in the Graphic Industry
Table 7.1. Compilation of spectral data (absorption maximum λ
max
and molar extinction coefficient ε
max
) of several NIR dyes studied as sensitizer for CtP applications (taken in MeOH), data were taken from [STR 14]
Table 7.2. Redox potentials for half wave oxidation and half wave reduction of NIR-sensitizers (taken in CH
3
CN) determined by cyclic voltammetry (taken in CH
3
CN) using a three-electrode setup with platinum disks as working respectively auxiliary electrode and Ag/AgCl electrodes as reference. Ferrocene was used as an internal standard and 0.1 M tetrabutylammonium hexafluorophosphate as supporting electrolyte. Data taken from [STR 14]
Table 7.3. Half wave reduction and corresponding LUMO energies of several acceptors determined by cyclic voltammetry (taken in CH
3
CN) using a three-electrode setup with platinum disks as working respectively auxiliary electrode and Ag/AgCl electrodes as reference. Ferrocene was used as an internal standard and 0.1 M tetrabutylammonium hexafluorophosphate (Bu
4
NPF
6
) as supporting electrolyte. Data taken from [STR 14]
Table 7.4. Redox potentials for half wave oxidation () of several donors determined by cyclic voltametry (taken in CH
3
CN) using a three-electrode setup with platinum disks as working respectively auxiliary electrode and Ag/AgCl electrodes as reference. Ferrocene was used as an internal standard and 0.1 M tetrabutylammonium hexafluorophosphate (Bu
4
NPF
6
) as supporting electrolyte. Data taken from [STR 14]
Table 7.5. Change of sensitivity and maximum of (dOD
plate
/dE)
max
of a NIR photopolymer comprising the NIR sensitizer Id4, the radical initiator [(p-C
4
H
9
PhI)
2
]
+
with different anions X
-
, a polymeric binder with 0.0015-0.0016 meq/g of COOH-groups, SR399 as monomer, SR 9053 as adhesion promoter, and copper phthalocyanine as colorant. The photopolymer was overcoated with poly(vinyl alcohol) as oxygen barrier. The imaging layer and oxygen barrier layer exhibited a coating weight of 1.2 g/m
2
and 0.6 g/m
2
, respectively. Exposure was carried out using a Kodak Trendsetter 800 as a function of exposure energy density (E) and processed in the Kodak developer SP500
Table 7.6. Summary of spectral data of some selected NIR-absorber dyes applied for laser drying with diode lasers emitting at 980 nm
9: Advanced Strategies for Spatially Resolved Surface Design via Photochemical Methods
Table 9.1. Overview of the conjugation methods used for inorganic substrate modification including the reaction conditions and the grafted species involved
Table 9.2. Overview of the conjugation methods used for biosurface modification including the reaction conditions and (bio)polymers involved
Guide
Cover
Table of Contents
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Dyes and Chromophores in Polymer Science
Edited by
Jacques Lalevée
Jean-Pierre Fouassier
Series EditorYves Rémond
First published 2015 in Great Britain and the United States by ISTE Ltd and John Wiley & Sons, Inc.
Apart from any fair dealing for the purposes of research or private study, or criticism or review, as permitted under the Copyright, Designs and Patents Act 1988, this publication may only be reproduced, stored or transmitted, in any form or by any means, with the prior permission in writing of the publishers, or in the case of reprographic reproduction in accordance with the terms and licenses issued by the CLA. Enquiries concerning reproduction outside these terms should be sent to the publishers at the undermentioned address:
ISTE Ltd
27-37 St George’s Road
London SW19 4EU
UK
www.iste.co.uk
John Wiley & Sons, Inc.
111 River Street
Hoboken, NJ 07030
USA
www.wiley.com
© ISTE Ltd 2015
The rights of Jacques Lalevée and Jean-Pierre Fouassier to be identified as the authors of this work have been asserted by them in accordance with the Copyright, Designs and Patents Act 1988.
Library of Congress Control Number: 2015932910
British Library Cataloguing-in-Publication Data
A CIP record for this book is available from the British Library
ISBN 978-1-84821-742-3
Preface
Light is involved in various chemical processes and its use in material science, and more particularly in polymer science, is growing in great strides. In this book, the use of light as a stimulus for chemical events encountered in the polymer science area is presented. Very different and important applications in polymer synthesis, data storage, photovoltaics (dye-sensitized solar cells), organic light-emitting devices (OLED) technology or biology use this innovative approach, for example.
One of the most challenging aspects in the field of chemistry is the design and development of high-performance systems requiring low energy consumption and with a low ecological impact. Today, photochemistry using visible light sources has become very attractive as a visible light is characterized by intrinsic advantages compared to an ultraviolet (UV) light (e.g. safety and availability of eco-friendly and cheap sources such as sunlight, halogen lamps, laser diodes and light-emitting diodes (LEDs)). Therefore, the use of visible light will be particularly emphasized.
The first three chapters of this book deal with the fundamentals in visible-light-induced polymer synthesis: free radical photopolymerization (Chapter 1), cationic photopolymerization (Chapter 2) and controlled radical photopolymerization (Chapter 3). Then, different applications in high-tech sectors are provided: curing of dental materials (Chapter 4), photoinitiated cross-linking in OLEDs (Chapter 5), photopolymers and laser drying in the graphic industry (Chapter 7), data storage using photopolymers (Chapter 8), surface modifications and design (Chapter 9), biology (Chapter 10), photovoltaic devices (Chapter 11) and self-healing of polymers induced by light (Chapter 12). Special mention of the use of dyes in dye-sensitized solar cells (DSSC) is also given (Chapter 6).
We believe that these exciting topics related to the development of photosensitive systems using dyes and various chromophores in polymer science and technology will be helpful for many readers (R&D researchers, engineers, technicians, university people, students, etc.). The examples presented in this book are still subject to fantastic evolutions and we hope they will herald a bright future in the coming years. We also hope that this book will provide the readers with a useful background in these different fields.
We would like to thank all the authors for their excellent work and all the fascinating discussions.
Professor Jean-Pierre FOUASSIER
Professor Jacques LALEVÉE
March 2015
1Trends in Dye Photosensitized Radical Polymerization Reactions
In this chapter, visible light-induced radical polymerization reactions in the 380–800 nm range are reviewed. The role of the absorbing species (dye) and the complete multicomponent photoinitiating systems (PISs) (dye and additives) are then emphasized. The original works on the dye-based PISs that have been proposed over the years are also outlined. However, this chapter is mainly focused on the latest developments, in the 2010–2014 period, and the actual trends of research, in particular the novel perspectives of applications under soft irradiation conditions.
1.1. Introduction
Dye photosensitized polymerization (DPP) (see [FOU 12a]) is a common expression often employed [OST 54, EAT 86, MON 93] to refer to a series of reactions where a dye1 (i) is excited by light [1.1a]2, (ii) leads [1.1b], alone or through primary or subsequent reactions involving one or more additional compounds, to radicals, cations or cation radicals, and (iii) initiates a free radical polymerization (FRP) [1.1c], a cationic polymerization (CP) [1.1d], a free radical promoted cationic photopolymerization (FRPCP) [1.1e], a concomitant cationic/radical polymerization (hybrid cure) (CCRP) [1.1f], a thiol-ene photopolymerization (TEP) [1.1g] or cross-linking reactions of prepolymers or polymers (this last point will not be covered here).
Therefore, by analogy with the term “initiator” in thermal polymerizations, the dye is also usually presented as a photoinitiator (PI), i.e. a substance that absorbs light and participates in the photoinitiation of a polymerization reaction. In the sense of photochemistry [TUR 90], however, it can also play the true role of a photosensitizer (PS) in some specific reactions3. Sometimes, there is an apparent ambiguity with the words “photoinitiator” and “photosensitizer” in papers dealing with photopolymerization. For the sake of clarity and convenience, we consider here that dye-based PISs can be classified into one-component PIS (I_Dye, [1.1a, 1.2]), two-component PIS (II_Dye, i.e. a dye and one additive ([1.1a], [1.3]–[1.5])), three-component PIS (III_Dye, i.e. a dye and two additives), etc. The additives can be electron donors (EDs) [1.3], electron acceptors (EAs) [1.4], hydrogen donors (HDs) [1.5] or electron/proton donors (EPDs) [1.6].
DPP reactions have been largely applied in various traditional and recently high-tech areas, such as radiation curing, imaging, graphic arts, optics, dentistry, medicine and nanomaterials (see [FOU 12a] and other relevant books [LAS 90, BOT 91, PAP 92, FOU 93b, KRO 94, REI 89, FOU 95a, SCR 97, KOL 97, DAV 99, NEC 99, FOU 99, CRI 99, FOU 01, DIE 02, BEL 03, FOU 06, SCH 07a, SCH 07b, LAC 08, MIS 09, ALL 10, FOU 10a, GRE 10, MAC 07]). For the past 50 years [OST 54], the large choice of available dyes and additives, and the possibility to tune the absorption in a given PIS by only changing the dye, has led to numerous research works. Recent developments have progressively allowed the use of increasingly less intense visible light sources. An important topic is now concerned with the adaptation of DPPs to irradiations with newly developed laser diodes and light emitting diodes (LEDs) for specific applications.
In many sectors, radical photopolymerization reactions are used more often than cationic photopolymerizations [FOU 12a, CRI 99, BEL 03, GRE 10]. Two historical facts can explain this difference. First, in industrial applications, the benefits versus the drawbacks are very often in favor of the radical processes. Second, many radical PISs have been successfully developed since the beginning of the 1960s. In contrast, industrial cationic PIs are only quasi-based on iodonium and sulfonium salts [CRI 79] (still largely used today) that are sensitive in the ultraviolet (UV). Later on, dialkylphenacylsulfonium, N-alkoxypyridinium, thianthrenium and ferrocenium salts, that absorb in the near UV/visible or visible range, have also been proposed [FOU 12a, CRI 99, BEL 03, KAH 10]. The photosensitization of onium salts in the visible range remains rather difficult (although successful results have been reached along the past years [FOU 12a, KAH 10]). Recent, promising developments using FRPCP should likely overcome this issue (see [FOU 12a, KAH 10] and below).
Thousands of papers have been already published in the field of DPPs. Before writing a novel review chapter, one question we can ask is: how can we present the most up-to-date situation? The first possibility, as is very often done, consists of providing a broad overview of the available systems which results in a qualitative list of PI, PS and compound/additive combinations. For obvious reasons, it is impossible to discuss their relative efficiency as the experimental conditions are completely different from one paper to another (film vs. solution, high-viscosity media vs. low-viscosity media, in laminate vs. under air, high light intensity vs. low light intensity, short exposure time vs. long exposure time, etc.). It could even happen that a proposed system (presented as a new system) is in the end not interesting from a practical point of view. The main interest of such reviews undoubtedly remains the gathering of the available systems. The second possibility, as sometimes encountered, consists of presenting the systems that are effectively used in a given field of applications. This represents a real interest as only the efficient systems are reported in that case. However, it requires us to have a review paper for each domain of applications. The third possibility, that is rather rare, consists of outlining the key points and the breakthroughs in the design of ever more reactive and efficient compounds, discussing the relative interest of the different systems toward the different uses, comparing the performances when possible and stressing the actual trends of development at a given time.
A recent book provides a detailed analysis of the encountered systems up to 2010/2011 (large overview, mechanism, reactivity and efficiency) [FOU 12a]; other previous books on the subject include [LAS 90, BOT 91, PAP 92, FOU 93b, KRO 94, REI 89, FOU 95a, SCR 97, KOL 97, DAV 99, NEC 99, FOU 99, CRI 99, FOU 01, DIE 02, BEL 03, FOU 06, SCH 07a, SCH 07b, LAC 08, MIS 09, ALL 10, FOU 10a, GRE 10] and [MAC 07]. Many review papers typically focusing on dyes as PIs or PSs [EAT 86, FOU 90, SCH 90b, URA 03, FOU 03, FOU 93a, FOU 95b, FOU 95c, FOU 00, TIM 93, CUN 93, GRE 93, CRI 93, FOU 11, FOU 10b, YAG 10, FOU 07, FOU 12b, FOU 12c, LAL 11b, XIA 15, LAL 15, SHA 14] or partly dealing with photoinitiation under visible lights [PAC 01, LAL 09b, LAL 09, LAL 10, LAL 12, IVA 10, MUF 10, LAL 14b, BON 14, SAN 14] have also been already published. As a result, we chose here to (i) provide a very brief overview of the PISs developed over the last 50 years, (ii) focus on the most recent literature and (iii) illustrate the today’s trends of development. Examples of these trends will concern the search of novel dyes for (i) polychromatic light excitations, (ii) blue, green and red laser light-induced polymerizations, (iii) photoinitiation under soft irradiation conditions, (iv) sunlight exposure, (v) enhanced absorption properties (red-shifted spectra and high molar extinction coefficients), (vi) the use as photoinitiator catalysts (PICs), (vii) dual radical/cationic PISs, (viii) performances attained under specific LED and laser diode exposures, (ix) concomitant radical/cationic photopolymerizations and the elaboration of interpenetrated polymer networks (IPNs), (x) TEPs, (xi) photopolymerizable panchromatic films or (xii) the manufacture of in situ nanoparticle (NP) containing films.
Our review here is limited to systems operating in dye photosensitized radical polymerizations (DPRPs) (see Figure 1.1). Their behavior in FRPCP reactions will be only evoked as all CPs are specifically covered in another covered in Chapter 2 of this book. In the same way, the role of dyes as part of PISs in the medical area, controlled radical photopolymerization reactions, printing technologies, stereolithography, optics or dyes under two-photon excitation are also discussed in detail in other chapters of this book.
Figure 1.1.Chemical mechanisms for dye photosensitized radical polymerizations
