Mechanochromic fluorescent materials : phenomena, materials and applications

284 Pages·2014·16.42 MB·English

by  Jiarui Xu, Zhenguo Chi, Royal Society of Chemistry (Great Britain)

Mechanochromic Fluorescent Materials
Phenomena, Materials and Applications
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RSC Smart Materials
Series Editors:
Hans-J¨org Schneider, Saarland University, Germany
Mohsen Shahinpoor, University of Maine, USA
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F Titles in this Series:
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22 1: Janus Particle Synthesis, Self-Assembly and Applications
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62 2: Smart Materials for Drug Delivery: Volume 1
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78 3: Smart Materials for Drug Delivery: Volume 2
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78 4: Materials Design Inspired by Nature
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9/ 5: Responsive Photonic Nanostructures: Smart Nanoscale Optical
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1 Materials
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oi:1 6: Magnetorheology: Advances and Applications
d 7: Functional Nanometer-Sized Clusters of Transition Metals: Synthesis,
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sc. 8: Mechanochromic Fluorescent Materials: Phenomena, Materials and
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Mechanochromic Fluorescent
Materials
Phenomena, Materials and Applications
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F Foreword
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1 Therecent,rapidexpansioninourunderstandingofthestructure-properties
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oi:1 relationship of many chemical compositions at the molecular level enables
g | d us design new functional materials useful for practical applications. One
or such group of materials is the so-called ‘‘smart materials’’, which are
c.
s.rs also called ‘‘stimuli-responsive’’ or ‘‘intelligent’’ materials. Some scientists
ub and engineers prefer to describe them as ‘‘designed materials’’. ‘‘Smart
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p:// materials’’, responding to external stimuli, undergo alteration in their
htt functional properties of mechanical, optical, including spectroscopic or
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o electromagnetic, behavior due to changes occurring in their molecular
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01 structure, composition or morphology. I believe that there would be no
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y objection to calling this century ‘‘the age of smart materials’’. These
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8 materials are leading the rapid innovative developments that we are pres-
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. n ently experiencing in many technological fronts, responding to pressing
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s This book, Mechanochromic Fluorescent Materials: Phenomena, Materials
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published on the topic of smart materials. This book is unique in that its
content covers a complete spectrum of the science and engineering of
mechanofluorochromic compounds and materials: low molar mass com-
pounds, polymers and their composites, organometallic complexes and
molecular aggregates or assemblies. This book not only guides us to novel
excitingnewdiscoveriesabouthowsomeofcompoundsandpolymersreveal
optical and spectroscopic responses to external stimuli, but also teaches us
molecular-level understanding of the changes, both in the chemical struc-
tural and micro- or macro-morphological levels. There are many expect-
ations that those materials will soon find a wide variety of advanced
technical applications. The topics of each chapter are superbly connected
and the overallcontents are very well balanced. This book is expected to be
RSCSmartMaterialsNo.8
MechanochromicFluorescentMaterials:Phenomena,MaterialsandApplications
EditedbyJiaruiXuandZhenguoChi
rTheRoyalSocietyofChemistry2014
PublishedbytheRoyalSocietyofChemistry,www.rsc.org
v
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vi Foreword
veryhelpfulforadvancedundergraduates,graduatestudentsandthosewho
would like to enter this particular area of research to attain an overall, but
relatively comprehensive view of the subject of this monograph.
I would like to extend a warm compliment to Prof. Jiarui Xu and
Prof.ZhenguoChi,editorsofthisbook,andallthecontributors,forbringing
05 us the science of the exciting new developments on the phenomena and
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P materials of mechanofluorochromism. It is my sincere hope that this book
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29- decorates brilliantly the desks and bookshelves of concerned students,
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23 scientistsandengineers.Onbehalfoftheauthors,Iwouldliketothankthe
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82 Royal Society of Chemistry for having selected such a wonderful topic and
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81 helping to publish this book in a very timely fashion.
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0 Jung-Il Jin
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10. Former President of IUPAC
oi: Distinguished Professor of Korea University
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9/ Chapter 1 Mechanofluorochromism: An Overview 1
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doi: References 5
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4 o 2.1 Introduction 7
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blis 2.2.3 Dumbbell-shaped Liquid Crystalline
Pu Dendritic Compounds 13
2.2.4 Heteropolycyclic D-p-A Compounds 24
2.2.5 Diphenylamine Carbazole Derivatives 26
2.2.6 Difluoroboron b-Diketonate Derivatives 30
2.2.7 Dipeptide-based Dyes 39
2.2.8 Triphenylamine Formaldehyde Derivatives 45
2.2.9 Benzodifuran Derivative 47
2.2.10 Anthrylpyrazole Derivatives 48
2.2.11 Benzothialdiazole-cored Phenylene
Vinylene Derivative 49
2.2.12 Salicylaldehyde Azine Derivatives 51
2.2.13 Cholesterol-appended Quinacridone
Derivatives 52
RSCSmartMaterialsNo.8
MechanochromicFluorescentMaterials:Phenomena,MaterialsandApplications
EditedbyJiaruiXuandZhenguoChi
rTheRoyalSocietyofChemistry2014
PublishedbytheRoyalSocietyofChemistry,www.rsc.org
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viii Contents
2.2.14 Siloxane-based Perylene Bisimide
Derivative 53
2.2.15 Anthraquinone Imide Derivatives 56
2.2.16 Distryrylfuran-substituted Maleimide
Complexes 57
07 2.2.17 Dicyanodistyrylbenzene Derivative 60
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http:// 3.2 Metal Complexes 73
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3.2.9 AIE Complexes 110
3.3 Conclusion 111
References 111
Chapter 4 Polymer Mechanofluorochromic Materials 114
Yi Zhang and Zhenguo Chi
4.1 Introduction 114
4.2 Synthetic Method 116
4.3 Mechanofluorochromic Polymer Systems 119
4.3.1 Based on Chemical Reaction of
Mechanophore-polymer 119
4.3.2 Based on Macromolecular Packing
Change 125
4.4 Conclusion 135
References 136
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Contents ix
Chapter 5 Mechanofluorochromic Polymer Composites 139
Siwei Liu and Zhenguo Chi
5.1 Introduction 139
5.2 The Preparation of the Polymer
07 Composites 141
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6.2.4 Mechanochromic Mechanism Based
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States 167
6.3 Relationship Between Structure and Properties
of Mechanofluorochromic Compounds 168
6.3.1 Relationship Between Crystallinity and
Mechanochromism 169
6.3.2 Relationship Between Alky (Alkoxy) Length
and Mechanochromism 186
6.4 Mechanofluorochromic Compounds 195
6.4.1 Diarylvinylanthracene Derivatives 195
6.4.2 Tetraphenylethylene Derivatives 197
6.4.3 Cyanoethylene Derivatives 206
6.4.4 Silole Derivative 220
6.4.5 Containing Multi-AIE Units 220
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6.4.6 Metal Complexes 223
6.4.7 Atypical AIE Mechanofluorochromic
Compounds 226
6.5 Conclusion 232
References 232
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