Photon-Working Switches (eBook)

Preface 5
A Success Story: International Research Group (IRG) PHENICS 7
List of International Publications Issued from the PHENICS Teams Involving French Groups (2009–2016) 10
Contents 14
Reviews for Photon-working Switch Systems 17
1 New Trends in Spiro-compounds Photochromic Metals Sensors: Quantitative Aspects 18
Abstract 18
1.1 Introduction 18
1.2 Quantitative Aspects of the General Properties of Spirocompounds: Gated Photochromism and Photomodulation 19
1.3 Structural, Spectroscopic, Equilibrium and Kinetic Aspects of Spirocompounds Metal Complexation 20
1.3.1 Structures of the Most Important Metal Complexing Spirocompounds 20
1.3.2 Compilation of the Quantitative Data 23
1.3.3 Structural Aspects of the Spirocompounds Complexation 23
1.3.4 Methodological Aspects of the Spirocompounds Complexation 32
1.3.5 Factors Determining the Complex Stability 34
1.3.6 Photodissociation of the Metal Complexes 39
1.4 Metal Sensing Systems and Devices 41
1.4.1 One-Metal Selective Spirocompounds 42
1.4.2 Two-Component Systems 43
1.4.3 Polymer Based Systems 43
1.4.4 Microfluidic Devices 45
1.4.5 Microchips 45
1.5 Conclusion 46
References 47
2 Novel Ethene-Bridged Diarylethene Photochromic Systems: Self-Assembly, Photoswitcher, and Molecular Logic Gates 51
Abstract 51
2.1 Introduction 51
2.2 Four-Membered Ring-Based Ethene Bridges 52
2.3 Five-Membered Ring-Based Ethene Bridges 53
2.4 Six-Membered Ring-Based Ethene Bridges 69
2.5 Metal Coordination Ligand-Based Ethene Bridges 75
2.6 Conclusion 78
References 78
3 Properties and Applications of Indolinooxazolidines as Photo-, Electro-, and Acidochromic Units 83
Abstract 83
3.1 Introduction 83
3.2 Structure and Synthesis of Indolinooxazolidine Derivatives 86
3.2.1 Structural Aspects of Indolinooxazolidine 86
3.2.2 Synthesis of Indolinooxazolidine Derivatives 88
3.3 The Acido- and Solvatochromic Properties of IndOxa and Their Applications 90
3.4 The Photochromic Properties of IndOxa and Their Uses as NLO Switches 94
3.5 The Electrochromic Properties of IndOxa and Their Uses as Multimode/Multistate Switches 99
3.6 Conclusion 102
References 102
4 Strategies for Switching with Visible Light 106
Abstract 106
4.1 Introduction 106
4.2 Direct Photoexcitation 108
4.2.1 Extended ?-Conjugation and Push–Pull Systems 109
4.2.2 Azobenzenes Completely Addressable in the Visible 111
4.3 Energy Transfer 113
4.3.1 Triplet Sensitization 114
4.3.2 Upconverting Nanoparticles 116
4.3.3 Multiphoton Absorption 117
4.4 Electron Transfer 119
4.5 Conclusion and Outlook 122
Acknowledgements 123
References 123
Development of Novel Photoswitches 128
5 Turn-On Mode Fluorescent Diarylethenes 129
Abstract 129
5.1 Introduction 129
5.2 Turn-On Mode Fluorescence Switching of Photochromic Diarylethenes Having Benzothiophene-1,1-Dioxide Groups 132
5.3 Highly Fluorescent Photochromic Diarylethenes 133
5.4 Effect of Alkyl Substituents on Fluorescent Properties 136
5.5 A Fluorescent Diarylethene that Turns on with Visible Light 138
5.6 Water-Soluble Fluorescent Diarylethenes Having Hydrophilic Substituents 140
5.7 Conclusions 141
References 141
6 Fluorescent Switchable Diarylethene Derivatives and Their Application to the Imaging of Living Cells 144
Abstract 144
6.1 Introduction 144
6.2 Nondestructive Readout Switchable Materials 146
6.2.1 Supramolecular Gel-Based Nondestructive Readout Switch 146
6.2.2 Organic Nanoparticle-Based Nondestructive Readout Switch 148
6.2.3 Inorganic Hybrid Nanoparticle-Based Nondestructive Readout Switch 150
6.3 Fluorescent Switchable Sensors and Images 152
6.3.1 Photochromic Fluorescent Probe to Image Living Cells 152
6.3.2 Fluorescent Diarylethene Switch Response to Metal Ions 155
6.3.3 Fluorescent Diarylethene Switch Response to Biomolecules 156
6.4 Conclusion and Prospects 161
Acknowledgements 161
References 161
7 Photochromism of Pentaarylbiimidazoles and Phenoxyl-Imidazolyl Radical Complexes 164
Abstract 164
7.1 Introduction 165
7.2 Photochromism of Pentaarylbiimidazole (PABI) 166
7.3 Photochromism of Phenoxyl-Imidazolyl Radical Complex 170
7.4 Conclusion 175
Acknowledgements 176
References 176
8 Diarylethenes that Photoswitch with Visible Light 179
Abstract 179
8.1 Introduction 180
8.2 Photoreactions Induced by Direct Photoexcitation with Visible Light 180
8.3 Photoreactions Induced by Indirect Photoexcitation via a Triplet Energy Transfer with Visible Light 185
8.4 Conclusion 189
References 189
9 Light-Sensitive Organic Recording Media for Three-Dimensional Optical Memory 191
Abstract 191
9.1 Introduction 191
9.2 Development of Photochromic Recording Media for Bitwise Working 3D Optical Memory 193
9.2.1 Synthesis and Characterization of Synthesized Compounds 193
9.2.1.1 Photochromic DAE 193
9.2.1.2 Photochromic Fulgimides 196
9.2.1.3 Photochromic Polymers with DAE and Fulgimide Fragments 196
9.2.1.4 Fluorescent Chromones 197
9.2.1.5 Photochromogenic Chromones 198
9.2.2 Development of Photochromic Polymeric Layers for 3D Bitwise Working Optical Memory 200
9.2.2.1 Layers with Nondestructive Refractive Readout 200
9.2.2.2 Layers with Nondestructive Fluorescence Readout 202
9.2.3 Development of Polymeric Layers for Archival 3D Optical Memory 205
9.2.4 Development of Multilayer Recording Media for 3D Optical Memory 206
9.2.5 Development of an Optical Device Prototype for Testing of Multilayer Recording Media and Disks on Functional Properties 208
9.3 Conclusions 211
Acknowledgements 211
References 211
10 Photochromism of Naphthopyrans Possessing a Spirophenanthrene Unit and the Ophthalmic Lens Comprising of Them 218
Abstract 218
10.1 Introduction 218
10.2 Typical Naphthopyrans and Their Photochromism 219
10.2.1 2H-Naphtho[1,2-b]Pyrans 220
10.2.2 3H-Naphtho[2,1-b]Pyrans 221
10.3 Photochromism of Naphthopyrans Possessing a Spirophenanthrene Unit 222
10.3.1 Effect of Spirophenanthrene Unit at C13 Position on Fading Reaction 223
10.3.2 Color Tuning 223
10.3.3 Effect of Electron-Donating Group on Phenyl Group at C2 Position 224
10.3.4 Effect of Electron-Donating Group at C11 Position 224
10.4 Plastic Photochromic Lenses Incorporating Naphthopyrans Possessing a Spirophenanthrene Unit 226
10.4.1 Design of the Matrix 227
10.4.2 Example of Gray and Brown Photochromic Lenses 229
10.5 Conclusion 230
Acknowledgements 230
References 230
Photophysics of Photoswitches 232
11 Multiphoton-Gated Photochromic Reactions Induced by Pulsed Laser Excitation 233
Abstract 233
11.1 Introduction 233
11.2 Multiphoton-Gated Cycloreversion Reaction in Diarylethene Derivatives 234
11.3 Multiphoton-Gated Cycloreversion Reaction in Fulgide Derivatives 238
11.4 One-Color Reversible Control of Photochromic Reactions in a Diarylethene Derivative Using Higher-Order Multiphoton Absorption 240
11.5 Conclusion 241
Acknowledgements 242
References 242
12 Ultrafast Photoswitching Dynamics of Azobenzenes with Intra- and Intermolecular Constraints 244
Abstract 244
12.1 Introduction 244
12.2 Ultrafast Spectroscopy of Optical Molecular Switches 246
12.3 Improved Photoswitching in Diazocines 248
12.4 Sequential Photoisomerisation Dynamics in a Push–Pull AB 252
12.5 Photoisomerisation of Azobenzenes in Complex Environments 256
12.6 Conclusions 259
Acknowledgements 260
References 260
13 Polyfunctional Photochromic Magnetic Materials Based on 3D Metal (Tris)Oxalates 267
Abstract 267
13.1 Introduction 267
13.2 Design of Bifunctional Systems with Magnetic Anions of 3D Metals with Bridging Bidentate Ligands and Photochromic Cations 268
13.2.1 Magnetic Sublattice 268
13.2.2 Photochromic Sublattice 271
13.3 Synthesis, Structure and Properties of Para- and Ferromagnetic Crystals with Photochromic Cations of the Spirocyclic Series 276
13.4 Synthesis and Properties of Materials Based on Photochromic (Tris)Oxalates of 3D Metals 283
13.4.1 Ordered Nanostructures [37] 283
13.4.2 Polymeric Composites 286
13.5 Conclusion 287
Acknowledgements 288
References 288
14 Photo-Modulation of Superconducting and Magnetic Properties 291
Abstract 291
14.1 Introduction 291
14.2 Modulation of Superconducting Property of Boron-Doped Diamond 292
14.2.1 Termination-Dependent Critical Current Density 293
14.2.2 Photo-Amplification of Critical Current Density 295
14.3 Photo-Modulation of Magnetism of Prussian Blue by Electron Injection 300
14.4 Conclusion 303
References 304
15 NMR Spectroscopy to Investigate Switching Reactions 306
Abstract 306
15.1 Introduction 306
15.2 Multiaddressable Switches 308
15.3 Metal-Ion Complexation of Photochromic Compounds with Crown Ethers 311
15.3.1 Metal Complexation of Chromenes Associated with Crown Ether Moiety 311
15.3.2 Metal-Ion Complexation of Bis(Styryl) Macrocyclic Tweezers 314
15.4 In Situ Laser Irradiation Coupled to NMR 317
15.5 Conclusion 321
Acknowledgements 321
References 321
16 Modeling Diarylethene Excited States with Ab Initio Tools: From Model Systems to Large Multimers 325
Abstract 325
16.1 Introduction 326
16.2 Model Systems: Understanding the Photochromism 327
16.2.1 Model Diarylethenes 327
16.2.2 Difference Between Normal and Inverse Diarylethenes 331
16.2.3 Side-Product Formation 333
16.3 Large Diarylethenes: Spectroscopy with TD-DFT 334
16.3.1 Simplified Photochromism Prediction 335
16.3.2 Optical Spectra 336
16.3.3 DTE Multimers 338
16.4 Conclusion 341
Acknowledgements 341
References 341
Supramolecular Photoswitches 346
17 Photochromic Crown Ethers 347
Abstract 347
17.1 Introduction 347
17.2 Crown-Containing Spiropyrans and Spironaphthooxazines 348
17.3 Crown-Containing Benzo- and Naphthopyrans 351
17.4 Crown-Containing Styryl Dyes 353
17.5 Crown-Containing Photochromes of Different Types 355
17.6 Supramolecular Assemblies of Crown Ethers and Photochromic Molecules 357
17.7 Conclusion 359
Acknowledgements 360
References 360
18 Linear and Nonlinear Optical Molecular Switches Based on Photochromic Metal Complexes 364
Abstract 364
18.1 Introduction 364
18.2 Bis-DTE-Based Bipyridine Derivatives 365
18.2.1 Normal (L) Versus Reverse (L?) Bipyridines 365
18.2.2 Photochromic Properties of Bipyridines (L) 366
18.2.3 Optical and Photochromic Properties of Bipyridines (L?) 368
18.3 Metal Complexes Incorporating One Photochromic Bipyridine Ligands 371
18.3.1 Bipyridine (L) Metal Complexes 371
18.3.1.1 Photochromic Properties 371
18.3.1.2 Photoregulation of the Quadratic NLO Properties 373
18.3.1.3 Photoregulation of the Luminescence Properties 374
18.3.2 Optical and Photochromic Properties of Bipyridine (L?) Metal Complexes 375
18.4 Octupolar Multi-DTE-Based Metal Complexes 376
18.4.1 Photochromic Properties 376
18.4.2 Quadratic NLO Studies 378
18.5 Photochromic Cyclometallated Platinum Complexes 378
18.5.1 Introduction 378
18.5.2 “Normal” Cyclometallated Platinum Complex 379
18.5.2.1 Synthesis and Photochromic Properties 379
18.5.2.2 Photoswitching of the NLO Response in Solution and in Thin Films 380
18.5.3 “Reverse” Cyclometallated Platinum Complex 381
18.5.3.1 Photochromic Properties 381
18.5.3.2 Sequential Double Modulation of the NLO Properties 382
18.6 Conclusions 383
Acknowledgements 383
References 383
19 Supramolecular Photochromism of Bis(phenanthrolinylthienyl)-Hexafluorocyclopentene 386
Abstract 386
19.1 Introduction 386
19.2 Molecular Design and Synthesis of 1,10-Phenanthroline-Attached Bisthienylperfluorocyclopentene 1o 387
19.3 Photochromic Behavior of 1o 388
19.4 Copper (I) Complexes of 1o and 1c 389
19.4.1 Preparation of the Cu(I) Complex 390
19.4.2 Job’s Plot 390
19.4.3 Search for Stable Structures of the Complexes by Calculations 391
19.4.4 Spectroscopic Properties of the Complexes 393
19.4.5 Section Conclusions 394
19.5 Control of the Precipitation-Dissolution Phenomena by Photochromism 395
19.5.1 Addition of Trifluoromethanesulfonic Acid 395
19.5.2 Addition of Oxalic Acid 396
19.5.3 Size and Shape of the Precipitated Solid Particles 397
19.5.4 Stable Structures Obtained by DFT Calculations 399
19.5.5 Powder X-Ray Diffraction Measurements 400
19.5.6 Quantum Yields of the Photoreactions 401
19.5.7 1H NMR DOSY Measurements 402
19.5.8 Section Conclusion 403
19.6 Conclusion 404
Acknowledgements 404
References 404
Photosynergy Effects of Photoswitches 407
20 Cooperative Self-assembly of Photochromic Diarylethenes at Liquid/Solid Interface and Highly Sensitive Photoinduced Transformation of the Ordering 408
Abstract 408
20.1 Introduction 408
20.2 Self-assembly and Photoinduced Transformation of Molecular Ordering of Photochromic Diarylethenes at Liquid/Highly Oriented Pyrolytic Graphite (HOPG) Interface [26] 409
20.3 Self-assembly and Photoinduced Transformation of Molecular Ordering of Diarylethenes Carrying Amide Group [27] 410
20.4 Cooperative Self-assembly of 2-Thienyl-Type Diarylethene and Photoinduced Transformation of the Ordering [28] 412
20.5 Effects of Alkyl Chain Length and Hydrogen Bonds on the Cooperative Self-assembly of 2-Thienyl-Type Diarylethene [30] 413
20.6 Cocrystallization and Mixing-Induced Cooperativity [31] 415
20.7 Conclusion 416
Acknowledgements 416
References 416
21 New Strategies for Light-Induced Alignment and Switching in Liquid Crystalline Polymers 419
Abstract 419
21.1 Introduction 420
21.2 Chromonic LCs and Organic–Inorganic Hybrids 421
21.2.1 Photoalignment of Chromonic LC 421
21.2.2 Photoalignment of Organic–Inorganic Hybrids 422
21.2.3 Vertical Alignment 423
21.3 Block Copolymer Films 426
21.3.1 Alignment Control of Microphase-Separated StructuresMicrophase-Separated Structures’ in the section heading ‘Alignment Control of Microphase Separated Structures’. 426
Outline placeholder 1
21.3.2 Photoalignment of Block Copolymer Films 426
21.3.3 In Situ Observations of MPS Alignment Change 427
21.4 Photocontrol from the Free Surface 431
21.5 Conclusion 435
Acknowledgments 436
References 436
22 Photoswitchable Hybrid Nanosystems Based on Diarylethene Molecules and Gold Nanoparticles 440
Abstract 440
22.1 Introduction 441
22.2 Design and Preparation Methods of Gold-Photochromic Hybrid Nanosystems 443
22.3 Influence of the Photoisomerization Process on the Surface Plasmon Resonance 446
22.4 Enhancement of the Photochromic Reaction by the Surface Plasmon Resonance 450
22.5 Theoretical Methodology and Investigation of the Photochromic–Plasmonic Interactions 454
22.5.1 From Isolated DTE to Gold Cluster/ DTE Hybrid System 455
22.5.2 Toward Molecular Plasmonics 457
22.6 Conclusion 459
Acknowledgements 459
References 460