Click polymerization

260 Pages·2018·25.356 MB·English

by  Qin, Anjun, Tang, Ben Zhong

Click Polymerization
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Polymer Chemistry Series
Editor-in-chief:
Ben Zhong Tang, The Hong Kong University of Science and Technology, Hong Kong,
1 China
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08- Series editors:
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10 Alaa S. Abd-El-Aziz, University of Prince Edward Island, Canada
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88 Jianhua Dong, National Natural Science Foundation of China, China
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81 Jeremiah A. Johnson, Massachusetts Institute of Technology, USA
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9/9 Toshio Masuda, Shanghai University, China
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g | 1: Renewable Resources for Functional Polymers and Biomaterials
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c. 2: Molecular Design and Applications of Photofunctional Polymers and
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n 5: Healable Polymer Systems
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9 28: Molecularly Imprinted Polymers for Analytical Chemistry Applications
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3 29: Photopolymerisation Initiating Systems
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Click Polymerization
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8- Edited by
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8 Anjun Qin
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1 South China University of Technology, China
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9 Email: [email protected]
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c. The Hong Kong University of Science and Technology, China
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oi: EPUB ISBN: 978-1-78801-501-1
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c.or Electronic ISSN: 2044-0804
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ps:// © The Royal Society of Chemistry 2018
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8-
0 Preface
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10. Click chemistry, conceptually coined by Sharpless and colleagues in 2001,
oi: refers to a class of elegant reactions with such wonderful advantages as
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g | high efficiency, regio- and/or stereospecificity, atom economy, and no
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c. offensive by-product. In 2002, the first click reaction, Cu(i)-catalyzed
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s.r azide–alkyne cycloaddition (CuAAC), was reported. Attracted by its fantas-
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p tic click merits, polymer scientists embarked on developing CuAAC into a
ps:// click polymerization. As a result, Cu(i)-catalyzed azide–alkyne click polym-
n htt erization (CuAACP) was successfully established and applied in preparing
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8 a number of functional polymers with linear and hyperbranched struc-
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20 tures. Inspired by the great success of CuAACP and thanks to the rapid
ust development of new click reactions of small molecules, such as thiol-ene/
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Au yne, Diels–Alder, and amino-yne click reactions, polymer scientists have
28 also successfully developed these reactions into new kinds of click polym-
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o erizations, i.e. thiol-ene/yne, Diels–Alder, and amino-yne click polymeriza-
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he tions, and so on.
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bli Thanks to the kind invitation from the editors of the Royal Society of
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Chemistry (RSC), we embarked on the preparation of this book, which is
specifically dedicated to the research of click polymerization. We invited a
group of active polymer scientists in the area to contribute to this book on
topics including transition metal-catalyzed and metal-free azide–alkyne click
polymerizations, catalyst-free click polymerization based on nitrile N-oxides,
thiol-yne click polymerization, proton transfer polymerization through thiol-
epoxy and amine-epoxy ‘click’ reactions and multicomponent polymeriza-
tion mediated by click chemistry.
This book is aimed at providing a valuable reference for readers who are
interested in click polymerization. Although we have tried our best to make
the book comprehensive, some important work may have been omitted, due

Polymer Chemistry Series No. 30
Click Polymerization
Edited by Anjun Qin and Ben Zhong Tang
© The Royal Society of Chemistry 2018
Published by the Royal Society of Chemistry, www.rsc.org
vii
View Online
viii Preface
to the limited space of the book and the rapid development in the area. Thus,
we hope that the readers will provide us with constructive comments, so that
we may modify the book in its next edition.
We would like to thank all of the authors of this book for their enthusias-
7 tic contributions. We also appreciate the Royal Society of Chemistry editors,
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P0 Mr Connor Sheppard, Dr Leanne Marle and Dr Robin Driscoll for their
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8- enthusiastic encouragement and technical support. We hope this book will
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0 stimulate new efforts, trigger new ideas, and encourage more scientists to
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8 devote themselves to further developing click polymerization.
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78 Anjun Qin
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9/ Center for Aggregation-Induced Emission
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10 State Key Laboratory of Luminescent Materials and Devices
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1 South China University of Technology
oi:
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c.or Department of Chemistry
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s.r The Hong Kong University of Science & Technology
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10. Chapter 1 Overview of Click Polymerization 1
oi: Die Huang, Anjun Qin and Ben Zhong Tang
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c. 1.1 Introduction 1
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ps:// Polymerization (RuAACP) 7
n htt 1.4 Metal-free Click Polymerization (MFCP) of
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8 Azides and Alkynes 9
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20 1.5 Organobase-mediated AACP 10
ust 1.6 Thiol-ene Click Polymerization 11
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Au 1.7 Thiol-yne Click Polymerization 12
28 1.7.1 Photo-/Thermo-initiated Thiol-yne
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o Click Polymerization 12
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he 1.7.2 Amine-mediated Thiol-yne Click
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1.7.3 Transition Metal-catalyzed Thiol-yne
Click Polymerization 16
1.7.4 Spontaneous Thiol-yne Click
Polymerization 17
1.8 Diels–Alder Click Polymerization 17
1.9 Other Click Polymerizations 19
1.10 Conclusion and Perspective 21
Acknowledgements 22
References 23

Polymer Chemistry Series No. 30
Click Polymerization
Edited by Anjun Qin and Ben Zhong Tang
© The Royal Society of Chemistry 2018
Published by the Royal Society of Chemistry, www.rsc.org
ix
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x Contents
Chapter 2 Transition Metal-catalyzed Click Polymerization 36
Die Huang, Anjun Qin and Ben Zhong Tang
2.1 Introduction 36
9 2.2 CuAACPs 37
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1 2.2.5 Cu(i) Complex-catalyzed AACP 60
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3 2.3 Ru(ii)-catalyzed AACP 74
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oi: Acknowledgements 78
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s.r Chapter 3 Metal-free Azide–Alkyne Click Polymerization 86
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pu Baixue Li, Anjun Qin and Ben Zhong Tang
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htt 3.1 Introduction 86
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8 o 3.2 MFCP of Aroylacetylenes and Azides 87
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st 3.4 MFCP of Activated Azides and Alkynes 104
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e References 114
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N-Oxides Applicable to Various Dipolarophiles 122
T. Takata, Y. Koyama and H. Sogawa
4.1 Introduction 122
4.2 Preparation Methods for Nitrile N-Oxides 126
4.3 Reactions of Nitrile N-Oxides 128
4.4 Aromatic Nitrile N-Oxides 132
4.4.1 Syntheses of Homoditopic Aromatic
Nitrile N-Oxides 132
4.4.2 Click Polymerization Using Aromatic
Nitrile N-Oxides 136
4.5 Aliphatic Nitrile N-Oxides 147
4.5.1 Syntheses, Structures and Reactions of
Aliphatic Nitrile N-Oxides 148
4.5.2 Click Polymerization and Cross-linking
Using Aliphatic Nitrile N-oxides 156
4.6 Conclusion 162