Aggregation-Induced Emission, 2 Volume Set
Fundamentals and Applications
Herausgeber: Qin, Anjun; Tang, Ben Zhong
Aggregation-Induced Emission, 2 Volume Set
Fundamentals and Applications
Herausgeber: Qin, Anjun; Tang, Ben Zhong
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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…mehr
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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.
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Produktdetails
- Produktdetails
- Verlag: Wiley
- Seitenzahl: 416
- Erscheinungstermin: 16. Dezember 2013
- Englisch
- Abmessung: 254mm x 196mm x 43mm
- Gewicht: 1678g
- ISBN-13: 9781118701690
- ISBN-10: 1118701690
- Artikelnr.: 38475251
- Herstellerkennzeichnung
- Libri GmbH
- Europaallee 1
- 36244 Bad Hersfeld
- 06621 890
- Verlag: Wiley
- Seitenzahl: 416
- Erscheinungstermin: 16. Dezember 2013
- Englisch
- Abmessung: 254mm x 196mm x 43mm
- Gewicht: 1678g
- ISBN-13: 9781118701690
- ISBN-10: 1118701690
- Artikelnr.: 38475251
- Herstellerkennzeichnung
- Libri GmbH
- Europaallee 1
- 36244 Bad Hersfeld
- 06621 890
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
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
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
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