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List of Contributors xiii
Preface xvii
1 Synthesis of Siloles (and Germoles) that Exhibit the AIE Effect 1Joyce Y. Corey
1.1 Introduction 1
1.2 Background 2
1.3 Synthesis of Siloles 4
1.4 Modification of Preformed Siloles 14
1.5 Related Germole Methodology 15
1.6 Metallaindenes and Metallafluorenes of Si and Ge 19
1.7 Oligomers and Polymers of Metalloles and Benzene-Annulated Metalloles 25
1.8 Summary and Future Directions 31
2 Aggregation-Induced Emission in Group 14 Metalloles (Siloles, Germoles, and Stannoles): Spectroscopic Considerations, Substituent Effects, and Applications 39Jerome L. Mullin and Henry J. Tracy
2.1 Introduction 39
2.2 Characteristics of AIE in the Group 14 Metalloles 44
2.3 Origins of AIE in Group 14 Metalloles: Restricted Intramolecular Rotation 48
2.4 Polymer Films and Polymerized Siloles 51
2.5 Applications of AIE-Active Metalloles 53
3 Aggregation-Induced Emission of 9,10-Distyrylanthracene Derivatives and Their Applications 61Bin Xu, Jibo Zhang and Wenjing Tian
3.1 Introduction 61
3.2 AIE Molecules Based on 9,10-Distyrylanthracene 63
3.3 AIE Mechanism of 9,10-Distyrylanthracene Molecule Systems 65
3.4 Application of AIE Luminogens Based on 9,10-Distyrylanthracene 67
3.5 Conclusion 80
4 Diaminobenzene-Cored Fluorophores Exhibiting Highly Efficient Solid-State Luminescence 83Masaki Shimizu
4.1 Introduction 83
4.2 1,4-Bis(alkenyl)-2,5-dipiperidinobenzenes 86
4.3 1,4-Diamino-2,5-bis(arylethenyl)benzenes 89
4.4 2,5-Diaminoterephthalates 93
4.5 2,5-Bis(diarylamino)-1,4-diaroylbenzenes 95
4.6 Applications 99
4.7 Conclusion 102
5 Aggregation-Induced Emission in Organic Ion Pairs 105Suzanne Fery-Forgues
5.1 Introduction 105
5.2 Historical Background 106
5.3 Preparation and Control of the Fluorophore Arrangement 107
5.4 AIE-Active Organic Ion Pairs in Nano- and Microparticles 111
5.5 Applications as Fluorescent Probes and Sensors for Analytical Purposes 115
5.6 Perspectives 122
6 Aggregation-Induced Emission Materials: the Art of Conjugation and Rotation 127Jing Huang, Qianqian Li and Zhen Li
6.1 Introduction 127
6.2 Rotation and Conjugation in AIE Molecules 128
6.3 Design of Functional Materials by Tuning the Conjugation Effect and Restricting Rotations 134
6.4 Outlook 151
7 Red-Emitting AIE Materials 155Xiao Yuan Shen, Anjun Qin and Jing Zhi Sun
7.1 Introduction 155
7.2 Basic Principles of Molecular Design for Red-Emitting Materials 156
7.3 Acquirement of Red-Emitting AIE Materials by Reconstruction of Traditional Red-Emitting Molecules 158
7.4 Preparation of Red-Emitting Materials by Introduction of Electron Donors/Acceptors into AIE-Active Molecules 162
7.5 Outlook 164
8 Properties of Triarylamine Derivatives with AIE and Large Two-Photon Absorbing Cross-Sections 169Jianli Hua, He Tian and Hao Zhang
8.1 Introduction 169
8.2 Design and Synthesis of Triarylamine Derivatives with AIE and 2PA 170
8.3 AIE Properties of Triarylamine Derivatives 170
8.4 One-Photon and Two-Photon Absorption Properties of Triarylamine Derivatives with AIE 176
8.5 Application of Triarylamine Materials with AIE and 2PA 180
8.6 Conclusion 181
9 Photoisomerization and Light-Driven Fluorescence Enhancement of Azobenzene Derivatives 185Mina Han and Yasuo Norikane
9.1 Introduction 185
9.2 Photoisomerization and Fluorescence of Azobenzene Derivatives 186
9.3 Aggregation-Induced Emission (AIE) 191
9.4 Fluorescence from Azobenzene-Based Aggregates 193
9.5 Conclusion 199
10 Supramolecular Structure and Aggregation-Induced Emission 205Hongyu Zhang and Yue Wang
10.1 Introduction 205
10.2 Hydrogen Bonding-Based Molecular Dimer and AIE 206
10.3 Quinacridine Derivatives with 1D Aggregation-Induced Red Emission 210
10.4 Multi-Stimuli-Responsive Fluorescence Switching of AIE/AIEE Luminogens 217
10.5 Pt Pt Interaction-Induced Emissive and Conductive 1D Crystals 222
10.6 Conclusion 226
11 Aggregation-Induced Emission in Supramolecular p-Organogels 233Pengchong Xue and Ran Lu
11.1 Introduction 233
11.2 Organogels Based on Discotic Molecules with AIE 234
11.3 Organogels Based on Rod-Like Molecules with AIE 238
11.4 Organogels Based on Banana-Shaped Molecules with AIE 242
11.5 Organogels Based on Dendritic Molecules with AIE 246
11.6 Conclusion 249
12 AIE-Active Polymers 253Rongrong Hu, Jacky W.Y. Lam and Ben Zhong Tang
12.1 Introduction 253
12.2 Polyolefins 254
12.3 Polyacetylenes 258
12.4 Polydiynes 259
12.5 Polyarylenes 263
12.6 Polytriazoles 269
12.7 Polysilylenevinylenes 271
12.8 Poly(Vinylene Sulfide)s 272
12.9 Other Systems 277
12.10 Conclusion 280
13 Enhanced Emission by Restriction of Molecular Rotation 285Jin-Long Hong
13.1 Background 285
13.2 Strategy to Restrict Molecular Rotation 286
13.3 Characterizations of Hindered Molecular Rotations 297
13.4 Conclusion 302
14 Restricted Intramolecular Rotations: a Mechanism for Aggregation-Induced Emission 307Junwu Chen and Ben Zhong Tang
14.1 Introduction: 2,3,4,5-Tetraphenylsilole, the Prototype Molecule of Aggregation-Induced Emission (AIE) 307
14.2 Crystal Structures of 2,3,4,5-Tetraphenylsiloles 310
14.3 Restricted Intramolecular Rotation (RIR) 312
14.4 Conclusion 320
15 Crystallization-Induced Emission Enhancement 323Yongqiang Dong
15.1 Introduction 323
15.2 Traditional Luminogens 324
15.3 Crystallization-Induced Emission Enhancement (CIEE) 324
15.4 Conclusion 333
16 Time-Resolved Spectroscopic Study of the Aggregation-Induced Emission Mechanism 337Bing-rong Gao, Hai-yu Wang, Qi-dai Chen and Hong-bo Sun
16.1 Introduction 337
16.2 Time-Resolved Spectroscopy 338
16.3 AIE Molecules Without Electron Donor-Acceptor Units 341
16.4 AIE Molecules with Electron Donor-Acceptor Units 344
16.5 Conclusion 353
17 Theoretical Understanding of AIE Phenomena Through Computational Chemistry 357Qian Peng, Yingli Niu, Qunyan Wu, Xing Gao and Zhigang Shuai
17.1 Introduction 357
17.2 Fundamental Photophysics Relating to AIE Phenomena 358
17.3 Computational Approaches to Investigate AIE Molecules 360
17.4 Computational Results 370
17.5 Summary and Outlook 389
18 Recent Theoretical Advances in Understanding the Mechanism of Aggregation-Induced Emission for Small Organic Molecules 399Jun-Ling Jin, Yun Geng and Zhong-Min Su
18.1 Introduction 399
18.2 Theoretical Methods 400
18.3 Recent Theoretical Advances in Understanding the Mechanism of Aggregation-Induced Emission 406
18.4 Prospects 413
Acknowledgments 414
References 414
Index 419
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