Aggregation-Induced Emission

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

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 Aggre