Table Of ContentHandbook of Aggregation- Induced Emission
Handbook of Aggregation- Induced Emission
Volume 2 Typical AIEgens Design
Edited by
Youhong Tang
Flinders University
Adelaide, Australia
Ben Zhong Tang
The Chinese University of Hong Kong
Shenzhen, China
This edition first published 2022
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Library of Congress Cataloging- in- Publication data applied for
Hardback (Volume 2): 9781119642985
Cover Design: Wiley
Cover Image: © Chad Baker/Getty Images
Set in 9.5/12.5pt STIXTwoText by Straive, Pondicherry, India
10 9 8 7 6 5 4 3 2 1
Pay our great respects to all the researchers who have contributed and are contributing to the study
of Aggregation Induced Emission (AIE).
vii
Contents
List of Contributors xvii
Preface to Handbook of Aggregation-Induced Emission xxiii
Preface to Volume 2: Typical AIEgens Design xxv
1 Tetraphenylpyrazine- based AIEgens: Synthesis and Applications 1
Ming Chen, Anjun Qin, and Ben Zhong Tang
1.1 Introduction 1
1.2 Synthesis of TPP- based AIEgens 3
1.2.1 Cyclization Reaction 3
1.2.2 Suzuki–Miyaura Reaction 7
1.3 Functionalities of TPP-b ased AIEgens 8
1.3.1 Organic Light- emitting Diodes 8
1.3.2 Fluorescent Sensors 9
1.3.3 Chiral Cage for Self- assembly to Achieve White- light Emission 13
1.3.4 Metal–organic Framework 15
1.4 Conclusion 17
References 18
2 AIEgens Based on 9,10- Distyrylanthracene (DSA): From Small Molecules
to Macromolecules 23
Leijing Liu, Bin Xu, and Wenjing Tian
2.1 Introduction 23
2.2 Application of AIE Luminogens Based
on 9,10- Distyrylanthracene 24
2.2.1 Smart Materials with Stimulus Response 24
2.2.1.1 Piezofluorochromic Materials 24
2.2.1.2 Photochromic Materials 27
2.2.1.3 Thermochromic Materials 27
2.2.1.4 Acidichromic Materials 27
2.2.1.5 Multistimuli- responsive Materials 30
2.2.2 High Solid- state Luminescent Materials 30
2.2.3 Fluorescent Materials for Bioimaging 35
2.2.4 Fluorescent Probes for Chemical and Biological Sensing 41
viii Contents
2.2.4.1 Fluorescent Probes for Chemical Sensing 41
2.2.4.2 Fluorescent Probes for Biological Sensing 44
2.3 Conclusions and Outlook 46
Acknowledgments 47
References 47
3 Typical AIEgens Design: Salicylaldehyde Schiff Base 53
Yue Zheng and Aijun Tong
3.1 Introduction 53
3.1.1 AIE and ESIPT of Salicylaldehyde Schiff Base 53
3.1.2 Universal Design of SSB- based AIEgens 55
3.2 Fluorescent Probes 55
3.2.1 Metal Ion Detection and Imaging 55
3.2.2 Biologically and Environmentally Related Molecular Detection and Imaging 63
3.2.3 Ratiometric pH Probes 76
3.2.4 Bioimaging 76
3.3 Fluorescent Materials 81
3.3.1 Solid Fluorescence Emitting and Stimuli-R esponsive Materials 81
3.3.2 Nanoparticles 88
3.4 Summary and Perspectives 91
References 92
4 Diaminodicyanoquinodimethanes: Fluorescence Emission Enhancement
in Aggregates and Solids 97
N. Senthilnathan and T. P. Radhakrishnan
4.1 Introduction 97
4.1.1 Molecular Materials 97
4.1.2 ‘Push–Pull’ Molecules 97
4.1.3 Diaminodicyanoquinodimethanes 98
4.2 Nonlinear Optical Materials based on DADQs 100
4.2.1 Molecular Hyperpolarizability 100
4.2.2 SHG Materials 100
4.2.3 Structure–Property Correlations 101
4.3 Enhanced Fluorescence in Aggregates and Solids Based on DADQs 102
4.3.1 Remote Functionalized Systems 102
4.3.2 Color Tuning, Nanocrystals, and Colloids 103
4.3.3 Ultrathin Films 105
4.3.4 New Directions 105
4.4 Mechanistic Insights into the Enhanced Fluorescence 106
4.4.1 Relevance of Intramolecular Effects 106
4.4.2 Role of Intermolecular Effects 106
4.5 Impact of Crystallinity on the Fluorescence Response 108
4.5.1 Amorphous- to- Crystalline Transformation: Fluorescence Switching and Tuning 108
4.5.2 Reversible Amorphous–Crystalline Transformations: Phase Change Materials 108
4.5.3 Impact of External Stimuli 110
4.6 Emergent and Potential Applications of DADQs 110
Contents ix
4.6.1 Electroluminescence and Nonlinear Optics 110
4.6.2 Bioimaging 110
4.6.3 Photoelectrochemical and Photobioelectrochemical Applications 112
4.6.4 Memory Devices 112
4.7 Concluding Remarks 113
Acknowledgements 114
References 114
5 Aggregation- induced Emission from the Sixth Main Group 119
Jan Balszuweit, Bibhisan Roy, and Jens Voskuhl
5.1 Introduction 119
5.2 Oxygen 119
5.2.1 Oxygen- Containing Heterocycles 120
5.2.2 Oxo- ether Containing AIE- Active Luminogens 122
5.3 Sulfur 126
5.3.1 Luminogens Based on Thiophenes 126
5.3.2 Thioethers with Aggregation- Induced Emission Properties 129
5.3.3 Emissive Sulfones 131
5.4 Selenium and Tellurium 132
5.4.1 Selenium- Containing Luminophores 132
5.4.2 Tellurium- Containing Luminophores 134
5.5 Conclusion 138
Acknowledgment 138
References 138
6 Fluorescence Detection of Dynamic Aggregation Processes Using AIEgens:
Hexaphenylsilole and Cyanostilbene 143
Fuyuki Ito
6.1 Introduction 143
6.2 Selective Detection of Phase Transformation During Evaporative Crystallization
of Hexaphenylsilole 145
6.3 Observation of the Initial Stage of Organic Crystal Formation During Solvent
Evaporation Using a Cyanostilbene Derivative 149
6.4 Chemometrix Analysis of the Aggregated Structure of Cyanostilbene in a
Reprecipitation Solution Using Fluorescence Excitation Spectroscopy 152
6.5 UV- triggered Fluorescence Enhancement of a Dicyanostilbene Derivative Film Cast
from an Ethanol Solution 158
6.6 Concluding Remarks 162
Acknowledgments 162
References 162
7 Cyclic Triimidazole Derivatives: An Intriguing Family of Multifaceted
Emitters 165
Elena Cariati, Elena Lucenti, Andrea Previtali, and Alessandra Forni
7.1 Introduction 165
7.2 The Protoype: Cyclic Triimidazole 166
