Supramolecular Soft Matter: Applications in Materials and Organic Electronics

SUPRAMOLECULAR SOFT MATTER......Page 3
CONTENTS......Page 7
Preface......Page 17
Contributors......Page 19
SECTION I Supramolecular Objects Towards Multi-task Organic Materials......Page 25
1.1 Introduction......Page 27
1.2 Hydrophobic–Amphiphilic Concept......Page 28
1.3.1 Hierarchical Supramorphology......Page 30
1.3.2 Antiwetting Architectures......Page 32
1.4.1 Supramolecular Molding Method......Page 34
1.5 Photoconductive Soft Materials......Page 36
1.5.2 Room Temperature Fullerene Liquids......Page 37
References......Page 39
2.1 Introduction......Page 43
2.2.2 Redox Response......Page 46
2.3 Reversible Stimuli-Responsive Methods......Page 48
2.3.1 Redox Switches......Page 49
2.3.2 Tuning the Amphiphilicity by Reversible Combination of Carbon Dioxide......Page 50
2.3.3 Photocontrolled Methods......Page 51
2.4.2 Hydrogen Bonding Method......Page 53
2.4.3 Host–Guest Modulation Employing Cyclodextrin as Host......Page 55
2.4.5 Charge-Transfer Interaction......Page 57
2.5 Conclusion and Outlook......Page 59
References......Page 60
3.1 Introduction......Page 67
3.2 Film-Type Supramolecular Hybrids......Page 68
3.3 Endo-Type Mesoporous Supramolecular Hybrids......Page 72
3.4 Exo-Type Mesoporous Supramolecular Hybrids......Page 75
References......Page 77
SECTION II Stimuli Responsive Dye Organized Soft Materials......Page 81
4.1 Introduction......Page 83
4.2 Azobenzene Dyes for Functional Materials......Page 84
4.3 Strategies for the Production of Functional Supramolecular Materials......Page 86
4.4.1 Polyelectrolyte-Based Materials......Page 87
4.4.2 Oligoelectrolyte-Based Materials......Page 90
4.5.1 Polymer-Based Materials......Page 93
4.6 Summary and Conclusions......Page 96
References......Page 97
5.1 Introduction......Page 101
5.2 Supramolecular Dye Assemblies with Stimuli-Responsive Optical Properties......Page 102
5.3 Supramolecular Dye Assemblies with Stimuli-Responsive Nanostructures......Page 106
References......Page 114
6.1 Introduction......Page 121
6.2 Hydrogen-Bonding-Based Anion-Responsive Supramolecular Gels......Page 123
6.3 Metal-Coordinated Gels Responsive to Anions......Page 127
6.4 Pyrrole-Based, Anion-Responsive π-Conjugated Molecules that form Supramolecular Assemblies......Page 129
6.5 Charge-By-Charge Assemblies from Anion-Responsive Supramolecular Gels......Page 135
References......Page 139
SECTION III Dimension Controlled Organic Frameworks......Page 143
7.1 Introduction......Page 145
7.2.1 Synthetic Routes toward Mesoporous Polymers......Page 147
7.2.2 Synthetic Schemes for Microporous Polymers......Page 148
7.2.3 Analysis of Porosity in Porous Polymers......Page 150
7.3.1 From 3D Semiconducting Molecules to Porous Polymer Networks......Page 151
7.3.2 Conjugated Microporous Polymers......Page 154
7.3.3 π-Conjugated Covalent Organic Frameworks......Page 157
7.3.4 Porous π-Conjugated Polymers Prepared via Hard\n\nor Soft Templating......Page 161
7.4.1 Graphitic Carbon Nitride......Page 164
7.4.2 Porous Graphitic Carbon Nitrides by Hard Templating......Page 167
7.4.3 Carbon Nitride-Based Semiconductor in Photocatalysis......Page 168
7.5 Conclusion......Page 169
References......Page 170
8.1 Introduction......Page 179
8.2 Two-Dimensional Polymers on Metal Surfaces......Page 181
8.3.1 Topological Design of 2D Porous Materials......Page 184
8.3.2 Control of Pore Size and Parameters......Page 186
8.3.3 Two-Dimensional COFs for Hydrogen Storage......Page 188
8.3.4 Two-Dimensional COFs for Other Gas Uptake......Page 190
8.3.5 Semiconducting Blue Luminescence 2D Polymers......Page 191
8.3.6 Photoconductive 2D Polymers......Page 192
8.4 Conclusions......Page 193
References......Page 194
9.1 Introduction......Page 199
9.2.2 Pore Size and Shape......Page 200
9.2.4 Flexibility......Page 201
9.3.1 Radical Polymerization of Vinyl Monomers......Page 202
9.4 Polymer Synthesis in Higher Dimensional Channels of MOFs......Page 205
9.4.2 Preparation of Three-Dimensional Porous Polymers......Page 206
9.5 Polymer–MOF Composites......Page 208
9.6 Summary......Page 210
References......Page 211
SECTION IV Recent Trends of Organic Radical Materials......Page 215
10.1.1 Organic Radicals: What Are They?......Page 217
10.1.2 Polychlorotriphenylmethyl Radicals: Molecular Structure and Properties......Page 218
10.1.3 Strategies Towards Multidimensionality......Page 220
10.2.2 Metal–Organic Complexes......Page 221
10.2.3 Hydrogen-Bonded Dimers with Tuneable Properties......Page 222
10.3 One Dimensional (1-D) Supramolecular Organizations......Page 223
10.4.1 Purely Organic Open Frameworks......Page 224
10.4.3 Surface-Driven 2-D Assemblies......Page 226
10.5.1 The Role of Chlorine–Chlorine Short Contacts in the 3-D Packing of PTM Radicals......Page 228
10.5.2 Truly 3-D Frameworks Based on PTM Radicals......Page 230
10.5.3 Three-Dimensional Assemblies on Surfaces Based on PTM Radicals......Page 231
10.6 Conclusions......Page 233
References......Page 234
11.1 Introduction......Page 239
11.2 Molecular Magnetism......Page 240
11.3 Intramolecular Magnetic Interaction......Page 241
11.5 Diarylethene as a Photoswitch......Page 242
11.6 Photoswitching of Magnetic Interaction......Page 244
11.8 Photoswitching Using Array of Photochromic Molecules......Page 247
11.9 Switching on Aryl Group......Page 249
11.11 Photoreaction on Metal Nanoparticles......Page 250
11.12 Conductance Photoswitching of Diarylethene–Gold Nanoparticle Network......Page 253
11.13 Conductance Switching of Diarylethene–Gold Nanoparticle Network by Oxidization......Page 255
References......Page 256
SECTION V Organogels and Polymer Assembly......Page 261
12.1 Introduction......Page 263
12.2 Design of the Self-Oscillating Gel......Page 264
12.3.1 Self-Oscillation of the Gel Smaller than the Chemical Wavelength......Page 265
12.3.3 Peristaltic Motion of Gels with Propagation of Chemical Wave......Page 267
12.4.2 Mass Transport Surface Utilizing Peristaltic Motion of the Gel......Page 269
12.4.4 Control of Chemical Wave Propagation in a Self-Oscillating Gel Array......Page 271
12.4.5 Self-Oscillating Polymer Chains as a ‘‘Nano-Oscillator’’......Page 272
12.4.7 Fabrication of Microgel Beads Monolayer......Page 273
References......Page 276
13.1 Introduction......Page 279
13.2.1 Influence of Self-Assembly on Optical Absorption and Emission of Conjugated Polymers......Page 281
13.2.2 Molecular Structure, Self-Assembly, and Quantum Yield of Conjugated Polyelectrolytes......Page 283
13.2.3 Influence of Self-Assembly on Intramolecular Energy Transfer......Page 285
13.3.1 Langmuir–Blodgett......Page 287
13.3.3 Block Copolymers......Page 288
13.3.4 Liposomes and Polydiacetylene......Page 291
13.3.5 Electrostatic Assemblies......Page 292
13.3.6 Surfactant-Directed Liquid Crystalline Assembly......Page 294
13.4.1 DNA Sensors......Page 296
13.4.2 Ion Sensitive Field Effect Transistors......Page 298
13.4.3 Polydiacetylene Liposome-Based Ion Sensors......Page 299
13.5 Outlook and Future Work......Page 300
References......Page 301
SECTION VI Supramolecular Liquid Crystals......Page 305
14.1 Introduction......Page 307
14.2.1 Specific Interactions for Supramolecular Self-Assembly......Page 308
14.2.2 New Molecular Shapes and Architectures......Page 310
14.3.1 Ionic Functions......Page 313
14.3.2 Electronic Functions......Page 315
14.4 Summary and Outlook......Page 316
References......Page 318
15.1 Introduction......Page 325
15.1.1 Defining the Structures of Supermolecules......Page 327
15.2 Liquid-Crystalline Dendrimers......Page 330
15.2.2 Side-Chain Liquid Crystal Dendrimers and Multipedes......Page 332
15.2.3 Effect of Hard Core Scaffolds—Silsesquioxane Scaffolds......Page 334
15.2.4 Effect of Hard Core Scaffolds—Fullerene Scaffolds......Page 336
15.3.1 ‘‘Janus’’ Liquid-Crystalline Multipedes......Page 338
15.3.2 Functional Liquid-Crystalline Supermolecules......Page 339
15.3.3 Effect of the Chirality at the Core......Page 341
15.3.4 Complex Functional Multipedes......Page 342
References......Page 343
16.1 Introduction......Page 347
16.1.1 Liquid Crystals......Page 348
16.1.2 Chirality in Liquid Crystals......Page 349
16.2 Photoresponsive Liquid Crystals......Page 353
16.3.1 Chiral Nematics......Page 354
16.3.2 Chiral Smectic C (SmC*)......Page 362
16.3.3 Blue Phases......Page 364
References......Page 365
17.1 Introduction......Page 369
17.2 Smectics and Discotics as Anisotropic Organic Semiconductors......Page 370
17.2.1 Smectic Liquid-Crystalline Semiconductors......Page 372
17.2.2 Discotic Liquid-Crystalline Semiconductors......Page 375
17.3 Summary......Page 379
References......Page 381
SECTION VII Supramolecular Composites Based on Carbon Nanotubes......Page 385
18.1 Introduction......Page 387
18.3 Redox Reaction and Determination of Electronic States of Carbon Nanotubes......Page 388
18.4 DNA/Carbon Nanotube Hybrids......Page 390
18.6 Conductive Nanotube Honeycomb Film......Page 392
18.7 Nanotube/Polymer Gel near IR-Responsive Materials......Page 394
18.8 Electrocatalyst for Fuel Cell Using Soluble CNTs......Page 396
References......Page 398
19.1 Introduction......Page 405
19.2 Interaction of Polyaromatics with CNTs......Page 406
19.3 Interaction of Extended π –Systems with CNTs......Page 411
19.4 Interaction of Conjugated Macrocycles with CNTs......Page 415
19.5 Interaction of Ionic Liquids with CNTs......Page 419
19.6 Interaction of Metal Ion Complexes with CNTs......Page 421
19.7 Interaction of Surfactants with CNTs......Page 422
19.8 Interaction of Functional Dyes with CNTs......Page 423
19.9 Composites of Liquid Crystals and CNTs......Page 424
References......Page 425
20.1 Introduction......Page 431
20.2 Tuning SWCNT Devices Using SAMs Composed of Organic and Biological Molecules......Page 432
20.2.1 Tuning of the Contact Barrier in Single-Walled CNT-FETs with SAMs......Page 433
20.2.2 Modification of the Electrical Properties in Double-Walled Nanotube Devices using SAMs......Page 437
20.2.3 Modification of the Electrical Properties of Single-Walled Nanotube Devices using Nanoparticles......Page 440
20.2.4 Sensors Based on Contact Barrier Modulation......Page 441
20.3 Functional SWNT Devices Coated with Self-Assembled Organic or Biological Molecules......Page 442
20.3.1 SWNT Chemical Sensors using Self-Assembled Molecules......Page 443
20.3.2 Functional SWNT Devices Functionalized with Self-Assembled Biopolymers......Page 445
20.3.3 Applications of DNA-Wrapped SWNTs......Page 446
References......Page 448
SECTION VIII Optoelectronics Based on Supramolecular Assemblies......Page 453
21.1 Introduction......Page 455
21.2.1 Fullerene-Based Electron Donor–Acceptor Conjugates......Page 456
21.2.2 Fullerene-Based Electron Donor–Acceptor Hybrids......Page 459
21.3 Fullerenes in Solar Cells......Page 461
21.3.1 Polymers for BHJ Organic Solar Cells......Page 462
21.3.2 Fullerene Derivatives for BHJ Organic Solar Cells......Page 465
Acknowledgments......Page 467
References......Page 468
22.1 Introduction......Page 475
22.2 Principles of Supramolecular Organic Photovoltaic Devices......Page 476
22.3 Self-Assembly Based on Hydrophobic Interactions......Page 482
22.4 Self-Assembly Based on H-Bonding......Page 484
22.5 Supramolecular Hybrid Solar Cells......Page 487
22.6 Conclusion......Page 488
References......Page 490
SECTION IX Future Perspective in Supramolecular Soft Materials......Page 497
COMMENTARY 1 WHAT WILL BE THE ROSETTA STONE FOR THE NEXT-GENERATION SUPRAMOLECULAR CHEMISTRY?......Page 499
COMMENTARY 2 SUPRAMOLECULAR CHEMISTRY IN MATERIALS SCIENCE......Page 503
Index......Page 507