Chromic phenomena: technological applications of colour chemistry

Title:

Personal Author:

Bamfield, P. (Peter) 1939-

Publication Information:

Cambridge, UK : Royal Society Of Chemistry, 2001

ISBN:

9780854044740

Subject Term:

Color

Chromic materials

Added Corporate Author:

Royal Society of Chemistry (Great Britain)

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Chromic phenomena, or those produced by materials which exhibit colour in response to a chemical or physical stimulus, have increasingly been at the heart of 'high-tec' developments in a variety of fields in the last decade. Many of the newer technologies, which are at the cutting edge of research, are multi-disciplinary, involving researchers from areas as diverse as physics, biology, materials science and electronic engineering. Chromic Phenomena covers five main areas: Colour change materials, such as photochromic, thermochromic and electrochromic materials; Materials which absorb and reflect light - the classical dyes and pigments; Luminescent phenomena, including phosphorescence, fluorescence and electroluminescence; Materials which absorb light and transfer energy, eg photosensitisers, infra-red absorbers and laser-addressable compounds; Phenomena involving the manipulation of light by chemicals, such as liquid crystals, lustre pigments, optoelectronics and photonics Providing an entry point both for new researchers and for established ones, this book, with its emphasis on the technological applications of these chromic phenomena, develops and investigates new applications for colour chemistry. It will be of interest to industrialists and professionals in the biological, medicinal, electronics/telecommunications and colorant industries, as well as academics in these fields.

Author Notes

A Research Manager with ICI/Zeneca prior to his retirement, Peter Bamfield is now an international freelance consultant on colour chemistry

Introduction	p. 1
Chapter 1 Phenomena Involving a Reversible Colour Change	p. 7
1.1 Introduction	p. 7
1.2 Photochromism	p. 7
1.2.1 Main Chemical Classes	p. 8
1.2.2 Spirobenzopyrans	p. 9
1.2.2.1 Synthesis of Spiroindolinobenzopyrans	p. 9
1.2.2.2 Spectral Properties of Spiroindolinobenzopyrans and Analogues	p. 10
1.2.3 Spironaphthoxazines	p. 11
1.2.3.1 Synthesis of Spiroindolinonaphthoxazines and Analogues	p. 11
1.2.3.2 Spectral and Physical Properties of Spiroindolinonaphthoxazines	p. 13
1.2.4 Benzo and Naphthopyrans (Chromenes)	p. 15
1.2.4.1 Synthesis of Benzopyrans and Naphthopyrans	p. 16
1.2.4.2 Spectral and Physical Properties of Diarylnaphthopyrans	p. 17
1.2.5 Fulgides	p. 20
1.2.5.1 Synthesis of Fulgides and Derivatives	p. 21
1.2.5.2 Spectral and Physical Properties of Fulgides and Derivatives	p. 22
1.2.6 Diarylethenes	p. 23
1.2.6.1 Synthesis of Diheteroarylethenes	p. 24
1.2.6.2 Spectral and Physical Properties of Dithiophenylethenes	p. 25
1.2.7 Miscellaneous Photochromic Systems	p. 26
1.2.8 Applications of Photochromic Materials	p. 28
1.2.8.1 Applications in Ophthalmics	p. 29
1.2.8.2 Novelty Printing and Textile Applications	p. 30
1.2.8.3 Optical Memories and Switches	p. 30
1.2.8.4 Other Optical Applications	p. 32
1.2.8.5 Biological Applications	p. 33
1.3 Thermochromism	p. 33
1.3.1 Inorganic and Organometallic Materials	p. 34
1.3.2 Reversible Intrinsically Thermochromic Organic Systems	p. 34
1.3.2.1 Molecular Rearrangements	p. 34
1.3.2.2 Stereoisomerism	p. 36
1.3.2.3 Macromolecular Systems	p. 37
1.3.3 Reversible Indirect Thermochromic Systems	p. 37
1.3.4 Applications of Thermochromic Materials	p. 38
1.3.4.1 Composite Thermochromic Pigments	p. 38
1.3.4.2 Chromogenic Thermotropic Gels	p. 40
1.4 Ionochromism	p. 41
1.4.1 Ionochromic Compounds	p. 41
1.4.1.1 Phthalides	p. 41
1.4.1.2 Leucotriarylmethanes	p. 45
1.4.1.3 Fluorans	p. 45
1.4.1.4 Azo and Styryl Dyes	p. 46
1.4.1.5 Chelates and Crown Ethers	p. 46
1.4.2 Applications of Ionochromism	p. 48
1.4.2.1 Analytical Chemistry	p. 48
1.4.2.2 Carbonless Copying Paper	p. 50
1.4.2.3 Direct Thermal Printing	p. 50
1.4.2.4 Visualisation of Printing Plates	p. 52
1.4.2.5 In Flower Coloration	p. 52
1.5 Electrochromism	p. 53
1.5.1 Electrochromic Cells	p. 53
1.5.2 Electrochrome Types	p. 54
1.5.2.1 Solution Electrochromes	p. 55
1.5.2.2 Solution-Solid Electrochromes	p. 55
1.5.2.3 Solid Electrochromes	p. 55
1.5.3 Electrochromic Chemicals	p. 55
1.5.3.1 Inorganic Oxides	p. 55
1.5.3.2 Prussian Blue	p. 56
1.5.3.3 Metal Phthalocyanines	p. 57
1.5.3.4 Viologens (4,4'-bipyridylium salts)	p. 58
1.5.3.5 Polymeric Electrochromes	p. 58
1.5.3.6 Other Organic Electrochromes	p. 61
1.5.4 Applications of Electrochromism	p. 61
1.5.4.1 Rear-view Mirrors	p. 61
1.5.4.2 Smart Windows	p. 62
1.5.4.3 Displays	p. 64
1.6 Solvatochromism	p. 66
1.6.1 Solvent Polarity and Solvatochromic Shifts	p. 66
1.6.2 Applications of Solvatochromism	p. 67
1.6.2.1 Analysis of Oils	p. 67
1.6.2.2 Polymer Probes and Sensors	p. 68
1.6.2.3 Biological Probes	p. 68
1.7 Miscellaneous Chromisms	p. 69
1.7.1 Piezo and Tribochromisms	p. 69
1.7.2 Gasochromism	p. 70
1.7.3 Vapochromism	p. 70
1.7.4 Chronochromism	p. 70
1.8 References	p. 70
Chapter 2 Phenomena Involving the Absorption and Reflectance of Light	p. 75
2.1 Introduction	p. 75
2.2 Some Elements of Colour Physics Relating to Colorants	p. 76
2.2.1 Additive Colour Mixing	p. 76
2.2.2 Subtractive Colour Mixing	p. 77
2.2.3 The CIE System	p. 78
2.3 Classical Organic Dyes	p. 80
2.3.1 Structural Classes	p. 81
2.3.1.1 Azo Dyestuffs	p. 81
2.3.1.2 Cyclic and Polycyclic Quinones	p. 91
2.3.1.3 Azines, Oxazines and Thiazines	p. 95
2.3.1.4 Methines	p. 96
2.3.1.5 Triaryl Carbonium Dyes	p. 98
2.3.1.6 Phthalocyanines	p. 98
2.3.2 Application Processes	p. 99
2.3.2.1 The Dyeing and Printing of Textile Fibres	p. 99
2.3.2.2 Paper	p. 108
2.3.2.3 Leather	p. 108
2.3.2.4 Food	p. 108
2.3.2.5 Hair Coloration	p. 110
2.3.2.6 Biological Stains	p. 111
2.4 Pigments	p. 112
2.4.1 Organic Pigments	p. 113
2.4.1.1 Azo Pigments	p. 114
2.4.1.2 Metal Complexes	p. 117
2.4.1.3 Isoindolinone Pigments	p. 118
2.4.1.4 Phthalocyanines	p. 119
2.4.1.5 Quinacridones	p. 120
2.4.1.6 Perylenes and Perinones	p. 121
2.4.1.7 Polycyclic Quinones	p. 123
2.4.1.8 Diketo-pyrrolopyrroles	p. 124
2.4.1.9 Triaryl Carboniums	p. 124
2.4.2 Inorganic Pigments	p. 124
2.4.2.1 Iron Oxides	p. 125
2.4.2.2 Chromium Oxide	p. 126
2.4.2.3 Mixed Oxides	p. 126
2.4.2.4 Alternatives to Cadmium Pigments	p. 127
2.4.2.5 Chromate Pigments	p. 127
2.4.2.6 Ultramarine Pigments	p. 127
2.4.2.7 Iron Blue Pigments	p. 127
2.4.3 Special Effect Pigments	p. 128
2.4.4 Applications of Coloured Pigments	p. 128
2.4.4.1 Dispersion of Pigments	p. 129
2.4.4.2 Printing Inks	p. 129
2.4.4.3 Paints and Coatings	p. 130
2.4.4.4 Plastics	p. 130
2.4.4.5 Construction Materials and Ceramics	p. 131
2.5 Solvent Dyes	p. 131
2.6 Photographic Colour Chemicals	p. 132
2.6.1 Colour Photographic Process	p. 132
2.6.2 Colour Films and Papers	p. 133
2.6.2.1 Colour Reversal Film	p. 133
2.6.2.2 Colour Negative Film	p. 133
2.6.2.3 Colour Papers and Prints	p. 135
2.6.2.4 Instant Colour Photographic Films and Paper	p. 135
2.6.3 The Colour Forming Chemicals in Photography	p. 135
2.6.3.1 Colour Developers	p. 136
2.6.3.2 Colour Couplers and Derived Dyes	p. 136
2.6.3.3 Diffusion Couplers	p. 140
2.7 Digital Printing	p. 140
2.7.1 Ink Jet Printing	p. 142
2.7.1.1 Continuous Ink Jet	p. 143
2.7.1.2 Drop-on-demand Ink Jet	p. 143
2.7.1.3 Colorants in Ink Jet Printers	p. 145
2.7.1.4 Commercial Applications of Ink Jet Technology	p. 147
2.7.2 Electrophotography	p. 147
2.7.2.1 Materials for Electrophotography	p. 149
2.7.2.2 Commercial Applications of Electrophotography	p. 151
2.8 References	p. 152
Chapter 3 Phenomena Involving Absorption of Energy and Emission of Light	p. 155
3.1 Introduction	p. 155
3.2 Luminescent Pigments	p. 157
3.2.1 Inorganic Phosphors	p. 158
3.2.1.1 Sulfides and Oxysulfides	p. 158
3.2.1.2 Oxygen-dominant Phosphors	p. 159
3.2.2 Synthesis and Formulation of Inorganic Phosphors	p. 159
3.2.3 Up-converters	p. 160
3.2.4 Applications of Inorganic Phosphors	p. 161
3.2.4.1 Phosphorescent Pigments	p. 161
3.3 Cathodoluminescence	p. 163
3.4 High Energy Photoluminescence	p. 166
3.4.1 Lighting	p. 166
3.4.2 Plasma Displays	p. 167
3.5 Fluorescence	p. 169
3.5.1 Fluorescent Chromophores	p. 170
3.5.1.1 Coumarins	p. 170
3.5.1.2 Naphthalimides	p. 172
3.5.1.3 Perylenes	p. 173
3.5.1.4 Benzanthrones, Anthraquinones, Benzoxanthones and Benzthioxanthones	p. 174
3.5.1.5 Xanthenes, Acridines and Oxazines	p. 176
3.5.1.6 Hydrocarbons	p. 179
3.5.1.7 Methines, Hemicyanines and Cyanines	p. 179
3.5.1.8 Dipyrromethines	p. 181
3.5.1.9 Miscellaneous Chromophores	p. 181
3.5.2 Applications as Fluorescent Dyes and Pigments	p. 182
3.5.2.1 Fluorescent Dyes in Textile Applications	p. 183
3.5.2.2 Daylight Fluorescent Pigments	p. 183
3.5.2.3 Other Applications	p. 184
3.5.3 Dye Lasers	p. 184
3.5.3.1 Types of Dye Lasers	p. 185
3.5.3.2 Mechanism of Dye Lasers	p. 186
3.5.3.3 Laser Dyes	p. 186
3.5.3.4 Applications of Dye Lasers	p. 186
3.5.4 Fluorescent Brighteners	p. 187
3.5.4.1 Stilbene Based Brighteners	p. 187
3.5.4.2 Ethylenic and Vinylic Based Brighteners	p. 191
3.5.4.3 Coumarins	p. 191
3.5.4.4 1,3-Diphenyl-2-pyrazolines	p. 192
3.5.4.5 Naphthalimides	p. 192
3.5.4.6 Polycyclics	p. 193
3.5.4.7 Quaternary Ammonium Compounds	p. 193
3.5.5 Fluorescence in Elemental Analysis	p. 193
3.5.6 Fluorescence in Biological, Medical and Drug Development Applications	p. 194
3.5.6.1 Fluorescence Instrumentation for Analysis	p. 194
3.5.6.2 Fluorophores and their Modification	p. 194
3.5.6.3 Probes for Calcium and Other Ions	p. 195
3.5.6.4 pH Indicators	p. 195
3.5.6.5 Membrane Potential Probes	p. 197
3.5.6.6 Lipid Membrane Probes	p. 198
3.5.6.7 Non-covalent Labelling Agents for DNA	p. 199
3.5.6.8 Covalent Labelling of Proteins and DNA	p. 199
3.5.6.9 Lanthanide Chelates in DNA and Protein Studies	p. 202
3.5.7 Luminescent Signalling for Sensors and Switches	p. 203
3.5.7.1 Charge Transfer Excited States (ICT and TICT)	p. 204
3.5.7.2 Photoinduced Electron Transfer States (PET)	p. 207
3.5.7.3 Molecular Information Processors	p. 209
3.5.8 Fluorescent Sensing of Biologically Important Gases	p. 211
3.5.9 Fluorescent Reagents in Photometric Chemical Sensors	p. 211
3.5.9.1 Ion-selective Optrodes	p. 213
3.5.9.2 Gas Sensors	p. 214
3.6 Chemiluminescence	p. 214
3.6.1 Chemiluminescent Reactions	p. 214
3.6.1.1 Luminol Oxidation	p. 215
3.6.1.2 Acridinium Compounds	p. 215
3.6.1.3 Dioxetanes	p. 216
3.6.2 Chemiluminescent Applications	p. 216
3.7 Bioluminescence	p. 218
3.7.1 Bioluminescent Systems	p. 218
3.7.1.1 Firefly Luciferins	p. 218
3.7.1.2 Bacterial Luciferases	p. 218
3.7.1.3 Imidazopyrazine Luciferins and Photoproteins	p. 219
3.7.2 Applications of Bioluminescence	p. 220
3.8 Electroluminescence	p. 221
3.8.1 Semi-conductor Light Emitting Diodes	p. 221
3.8.2 Electroluminescent Display Technologies	p. 224
3.8.3 Inorganic EL Displays	p. 224
3.8.3.1 Powder EL	p. 225
3.8.3.2 Thin-film EL	p. 225
3.8.4 Organic Light Emitting Diodes	p. 227
3.8.5 Low Molecular Weight Organic LED	p. 227
3.8.5.1 Low MW Materials	p. 228
3.8.5.2 Full-colour OLED Displays	p. 230
3.8.6 Polymer Light Emitting Diodes	p. 232
3.8.6.1 Synthesis of the Polymers	p. 233
3.8.6.2 Full-colour LEP Displays	p. 237
3.8.7 Commercial Prospects for OLEDs	p. 238
3.9 Triboluminescence	p. 239
3.10 References	p. 241
Chapter 4 Phenomena Involving Absorption of Light and Energy Transfer	p. 245
4.1 Introduction	p. 245
4.2 Laser Addressable Compounds (Infrared Absorbers)	p. 245
4.2.1 Chemical Classes of Near-IR Absorbers	p. 246
4.2.1.1 Cyanines	p. 247
4.2.1.2 Squarylium and Croconium Dyes	p. 249
4.2.1.3 Iminium Salts	p. 250
4.2.1.4 Triphenylmethanes	p. 250
4.2.1.5 Nickel Dithiolenes	p. 251
4.2.1.6 Quinones	p. 251
4.2.1.7 Phthalocyanines	p. 253
4.2.2 Applications of Laser Addressable Compounds and Near-IR Absorbers	p. 255
4.2.2.1 Energy Conversion	p. 255
4.2.2.2 Protection from IR Radiation	p. 257
4.3 Optical Data Storage	p. 259
4.3.1 Optical Data Storage using Dyes	p. 260
4.3.2 Developments in Optical Data Storage	p. 263
4.4 Organic Photoconductors	p. 264
4.4.1 Charge Generation Materials	p. 265
4.4.1.1 Azo Pigments	p. 266
4.4.1.2 Phthalocyanines	p. 267
4.4.1.3 Other CGMs	p. 267
4.4.2 Charge Transport Materials	p. 269
4.5 Photosensitisers	p. 270
4.5.1 Sensitisers in Photochemical Synthesis	p. 271
4.5.2 Photosensitisers in Polymerisation	p. 271
4.5.3 Sensitisers in Colour Photography	p. 277
4.6 Applications of Sensitisers in Medicine and Chemical Biology	p. 278
4.6.1 Photomedicine	p. 280
4.6.2 Photodynamic Therapy	p. 280
4.6.2.1 The Mechanism of PDT	p. 281
4.6.2.2 Photosensitisers for PDT	p. 281
4.6.2.3 Light Sources for PDT	p. 286
4.6.2.4 Use against Viruses and Bacteria	p. 286
4.6.3 Photodiagnosis and Imaging	p. 287
4.6.4 Photoinsecticides	p. 288
4.7 Solar Energy Utilisation	p. 289
4.7.1 Solar Cells and Electrical Energy	p. 289
4.7.1.1 Inorganic and Organic Photovoltaics	p. 290
4.7.1.2 Dye-sensitised Solar Cells	p. 292
4.7.2 Artificial Photosynthesis	p. 295
4.7.2.1 Light Harvesting Antennae	p. 297
4.7.2.2 Artificial Reaction Centres	p. 297
4.7.3 The Production of Useful Chemicals	p. 298
4.7.3.1 Water Splitting	p. 300
4.7.3.2 Carbon Dioxide Reduction	p. 300
4.7.4 Enhancement of Natural Photo-processes	p. 300
4.8 References	p. 301
Chapter 5 Phenomena Involving the Manipulation of Light	p. 305
5.1 Introduction	p. 305
5.2 Liquid Crystals	p. 305
5.2.1 Nematic Liquid Crystals and their Applications	p. 306
5.2.1.1 Twisted Nematic Displays	p. 306
5.2.1.2 Nematic Liquid Crystal Materials	p. 308
5.2.1.3 Colour Displays from Twisted Nematic Liquid Crystals	p. 310
5.2.2 Cholesteric Liquid Crystals and their Applications	p. 312
5.2.2.1 Guest-Host LCDs	p. 314
5.2.2.2 Temperature Sensing and Novelty Applications	p. 316
5.2.2.3 Polymeric Cholesteric Liquid Crystals	p. 317
5.2.2.4 Full-colour Recording using Cholesteric Phases	p. 317
5.2.3 Luminescent Liquid Crystals	p. 319
5.2.3.1 Fluorescent Liquid Crystals	p. 319
5.2.3.2 Polarised Electroluminescent Liquid Crystals	p. 320
5.2.4 Polymer-dispersed Liquid Crystals	p. 321
5.2.5 Side Chain Polymeric Liquid Crystals	p. 322
5.3 Colours from Reflection, Interference and Diffraction	p. 323
5.3.1 Lustre and Colour Variable Pigments	p. 323
5.3.1.1 Optical Basis for Lustre Pigments	p. 324
5.3.1.2 Material, Construction and Processes	p. 325
5.3.1.3 Applications of Lustre/Colour Variable Pigments	p. 327
5.3.2 Iridescent Fibres	p. 329
5.4 Holography	p. 329
5.4.1 Principles of Holography	p. 330
5.4.2 Materials Used in Holography	p. 332
5.4.3 Applications of Holography	p. 332
5.4.3.1 Graphic Arts and Design	p. 333
5.4.3.2 Holographic Optical Elements in Liquid Crystal Display Systems	p. 334
5.4.3.3 Holographic Data Storage	p. 335
5.5 Laser Diodes	p. 337
5.5.1 Inorganic Semi-conductor Laser Diodes	p. 337
5.5.2 Organic Lasers	p. 338
5.5.2.1 Use of Luminescent Conjugated Polymers	p. 339
5.5.2.2 Single Crystal Organic Materials	p. 340
5.6 Opto-electronics	p. 341
5.6.1 Basis of Non-linear Optics	p. 341
5.6.2 Non-linear Optical Materials	p. 342
5.6.2.1 Non-linear Optical Chromophores	p. 342
5.6.2.2 Non-linear Optical Polymers	p. 344
5.6.3 Photorefractive Polymers	p. 347
5.6.3.1 The Photorefractive Effect	p. 348
5.6.3.2 Amorphous Polymers and Composites	p. 348
5.6.3.3 Photorefractive Polymer-dispersed Liquid Crystals	p. 349
5.6.3.4 Applications of Photorefractive Materials	p. 350
5.7 Photonics	p. 350
5.7.1 Photonic Band Gap Crystals	p. 351
5.7.1.1 Photonic Crystals via Self-assembly of Colloidal Spheres	p. 351
5.7.1.2 Inverse Opals	p. 351
5.7.1.3 Lithographic Fabrication of Photonic Band Gap Materials	p. 353
5.7.2 Applications of Photonic Crystals	p. 353
5.8 References	p. 353
Bibliography	p. 357
Subject Index	p. 363

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