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Aggregation-Induced Emission (AIE) is a novel photophysical phenomenon which offers a new platform for researchers to look into the light-emitting processes from luminogen aggregates, from which useful information on structure-property relationships may be collected and mechanistic insights may be gained. The discovery of the AIE effect opens a new avenue for the development of new luminogen materials in the aggregate or solid state. By enabling light emission in the practically useful solid state, AIE has the potential to expand significantly the technological applications of luminescent…mehr
Aggregation-Induced Emission (AIE) is a novel photophysical phenomenon which offers a new platform for researchers to look into the light-emitting processes from luminogen aggregates, from which useful information on structure-property relationships may be collected and mechanistic insights may be gained. The discovery of the AIE effect opens a new avenue for the development of new luminogen materials in the aggregate or solid state. By enabling light emission in the practically useful solid state, AIE has the potential to expand significantly the technological applications of luminescent materials. Aggregation-Induced Emission: Fundamentals is the first book to explore the fundamental issues of AIE, including the design, synthesis, and photophysical behavior of AIE-active molecules and polymers. The control of the morphological structures of the aggregates of AIE-active materials, and the experimental investigation and theoretical understanding of the AIE mechanism, are also covered in this volume. Topics covered include: * AIE in group 14 metalloles * AIE in organic ion pairs * Red light-emitting AIE materials * Supramolecular structure and AIE * AIE-active polymers * Enhanced emission by restriction of molecular rotation * Crystallization-induced emission enhancement * Theoretical understanding of AIE phenomena This book is essential reading for scientists and engineers who are designing optoelectronic materials and biomedical sensors, and will also be of interest to academic researchers in materials science and physical and synthetic organic chemistry, as well as physicists and biological chemists.
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ANJUN QIN Department of Polymer Science and Engineering, Zhejiang University, China BEN ZHONG TANG Department of Chemistry, The Hong Kong University of Science and Technology, China
Inhaltsangabe
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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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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