Aggregation-Induced Emission, 2 Volume Set Fundamentals and Applications

Edited by Professor Tang, who first discovered this phenomenon, this 2-volume reference addresses the fundamentals of Aggregation-Induced Emission (AIE).  The book presents an overview of this rapidly emerging and exciting area of research, inviting scientists to renew their photophysical knowledge and stimulate new developments in the field.  Covering fundamental issues of AIE, this reference work also discusses the design and synthesis of AIE-active molecules; includes an introduction to AIE, polymers with AIE characteristics and crystallization-induced emission enhancement. Mechanistic understanding of AIE processes are included, along with a discussion of the progress in the theoretical investigation of AIE mechanism and understanding of AIE mechanism by time-resolved spectrum measurements.

Professor Ben Zhong Tang, The Hong Kong University of Science & Technology, Hong Kong
Ben Zhong Tang, is a Chair Professor in the Department of Chemistry at The Hong Kong University of Science & Technology. He is interested in the creation of new molecules with novel structures and unique properties. The Aggregation-Induced Emission (AIE) phenomenon was first discovered by Professor Tang and the first paper about AIE was published by Tang and coworkers in 2001; this paper has already been cited over 600 times. Professor Tang has acted as a guest editor for Macromolecular Chemistry and Physics, organizing three special Series on Functional Polymers. He also organized a special issue in the Journal of Inorganic and Organometallic Polymers and Materials to honor of Professor Ian Manners in 2007. He is currently serving as Editor-in-Chief of the Polymer Chemistry Series and Editor of Polymer Bulletin.

Professor Anjun Qin, Department of Polymer Science & Engineering, Zhejiang University, China
Anjun Qin is an Associate Professor in the Department of Polymer Science and Technology at Zhejiang University, China. One of his research interests is to design and synthesize polymers with AIE characteristics and to explore their applications in chemosensors and bioprobes.
Between them, the editors have published more than 400 peer-reviewed papers and 40 book chapters.

List of Contributors xiii

Preface xvii

1 Synthesis of Siloles (and Germoles) that Exhibit the AIE Effect 1
Joyce 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

References 33

2 Aggregation-Induced Emission in Group 14 Metalloles (Siloles, Germoles, and Stannoles): Spectroscopic Considerations, Substituent Effects, and Applications 39
Jerome 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

References 54

3 Aggregation-Induced Emission of 9,10-Distyrylanthracene Derivatives and Their Applications 61
Bin 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

Acknowledgments 80

References 80

4 Diaminobenzene-Cored Fluorophores Exhibiting Highly Efficient Solid-State Luminescence 83
Masaki 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

Acknowledgments 102

References 103

5 Aggregation-Induced Emission in Organic Ion Pairs 105
Suzanne 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

Acknowledgments 122

References 123

6 Aggregation-Induced Emission Materials: the Art of Conjugation and Rotation 127
Jing 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

References 152

7 Red-Emitting AIE Materials 155
Xiao 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

Acknowledgments 165

References 165

8 Properties of Triarylamine Derivatives with AIE and Large Two-Photon Absorbing Cross-Sections 169
Jianli 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

References 182

9 Photoisomerization and Light-Driven Fluorescence Enhancement of Azobenzene Derivatives 185
Mina 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

References 199

10 Supramolecular Structure and Aggregation-Induced Emission 205
Hongyu 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

References 227

11 Aggregation-Induced Emission in Supramolecular p-Organogels 233
Pengchong 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

References 250

12 AIE-Active Polymers 253
Rongrong 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

References 280

13 Enhanced Emission by Restriction of Molecular Rotation 285
Jin-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

References 303

14 Restricted Intramolecular Rotations: a Mechanism for Aggregation-Induced Emission 307
Junwu 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

Acknowledgments 320

References 320

15 Crystallization-Induced Emission Enhancement 323
Yongqiang Dong

15.1 Introduction 323

15.2 Traditional Luminogens 324

15.3 Crystallization-Induced Emission Enhancement (CIEE) 324

15.4 Conclusion 333

References 334

16 Time-Resolved Spectroscopic Study of the Aggregation-Induced Emission Mechanism 337
Bing-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

Acknowledgments 354

References 354

17 Theoretical Understanding of AIE Phenomena Through Computational Chemistry 357
Qian 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

References 390

18 Recent Theoretical Advances in Understanding the Mechanism of Aggregation-Induced Emission for Small Organic Molecules 399
Jun-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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