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Book Details
Abstract
Click chemistry describes organic reactions which are highly efficient, regioselective and allow for mild reaction conditions. The archetypal click reaction of Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) is used in many diverse areas and has been extensively developed for polymer synthesis, leading to the term of click polymerization. This technique enables the preparation of functional polymers with linear and topological structures that have the potential to be used in optoelectronics and biological fields.
Edited by world renowned experts, Click Polymerization is the first book to comprehensively summarize this approach to polymer synthesis consolidating all the different reaction types in one resource. From the basic knowledge through to the latest developments in synthesis, chapters include transition-metal catalysed and metal-free azide-alkyne click polymerizations as well as thiol-ene, thiol-yne and thiol-epoxy click polymerizations.
The book provides an authoritative guide to click polymerization techniques for graduate students and researchers interested in polymer chemistry and materials science.
Ben Zhong Tang received his BS and PhD degrees from SCUT and Kyoto University in1982 and 1988, respectively. He conducted his postdoctoral work at University of Toronto and worked as a senior scientist in Neos Co.,Ltd. in 1989– 1994. He joined HKUST in 1994 and was promoted to Chair Professor in 2008. He was elected to fellowships of the Royal Society of Chemistry (2013) and the Chinese Academy of Sciences (2009). He was awarded a number of prizes, such as Khwarizmi International Award (Iranian Organization for Science & Technology), State Natural Science Award (Chinese Government), MACRO2012 Lecture Award (ACS PMSE Division), and Senior Research Fellowship (Croucher Foundation). He has published >700 papers and his papers have been cited by peers for >20,000 times with an H index of 87. He has delivered >200 invited lectures at international conferences. He is serving as a News Contributor to Noteworthy Chemistry (ACS) and Editor-in-Chief of Polymer Chemistry Series and Associate Editor of Polymer Chemistry (RSC).
Anjun Qin received his BS and PhD degrees from Shanxi University and Chinese Academy of Sciences in 1999 and 2004, respectively. He did his postdoctoral research at The Hong Kong University of Science & Technology (HKUST) and Zhejiang University in 2005–2008. He joined Zhejiang University as an Associate Professor in 2008 and moved to South China University of Technology (SCUT) with promotion to Full Professor in 2013. He has published 160 papers and his papers have been cited by peers about 3700 times with an H index of 38. He was awarded the National Science Fund for Excellent Young Scholars in 2012.
Table of Contents
| Section Title | Page | Action | Price |
|---|---|---|---|
| Cover | Cover | ||
| Click Polymerization | i | ||
| Preface | vii | ||
| Contents | ix | ||
| Chapter 1 - Overview of Click Polymerization | 1 | ||
| 1.1 Introduction | 1 | ||
| 1.2 CuAACPs | 3 | ||
| 1.3 Ru(ii)-Catalyzed Azide–Alkyne Click Polymerization (RuAACP) | 7 | ||
| 1.4 Metal-free Click Polymerization (MFCP) of Azides and Alkynes | 9 | ||
| 1.5 Organobase-mediated AACP | 10 | ||
| 1.6 Thiol-ene Click Polymerization | 11 | ||
| 1.7 Thiol-yne Click Polymerization | 12 | ||
| 1.7.1 Photo-/Thermo-initiated Thiol-yne Click Polymerization | 12 | ||
| 1.7.2 Amine-mediated Thiol-yne Click Polymerization | 15 | ||
| 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 | ||
| Chapter 2 - Transition Metal-catalyzed Click Polymerization | 36 | ||
| 2.1 Introduction | 36 | ||
| 2.2 CuAACPs | 37 | ||
| 2.2.1 Mechanism of CuAAC | 37 | ||
| 2.2.2 CuSO4/SA-catalyzed AACP | 38 | ||
| 2.2.2.1 Preparation of PTAs with Linear Structures | 38 | ||
| 2.2.2.2 Preparation of PTAs with Hyperbranched Structures | 45 | ||
| 2.2.3 Photoinitiated CuAACP | 51 | ||
| 2.2.4 CuX-catalyzed AACP | 53 | ||
| 2.2.4.1 Preparation of PTAs with Linear Structures | 53 | ||
| 2.2.4.2 Preparation of Hyperbranched PTAs | 58 | ||
| 2.2.5 Cu(i) Complex-catalyzed AACP | 60 | ||
| 2.2.5.1 CuBr(PPh3)3-catalyzed AACP | 60 | ||
| 2.2.5.2 CuIP(OEt)3-catalyzed AACP | 66 | ||
| 2.2.5.3 Other Cu(i) Complex-catalyzed AACPs | 68 | ||
| 2.2.6 Supported Cu(i)-catalyzed AACP | 69 | ||
| 2.3 Ru(ii)-catalyzed AACP | 74 | ||
| 2.4 Conclusion and Perspective | 77 | ||
| Acknowledgements | 78 | ||
| References | 78 | ||
| Chapter 3 - Metal-free Azide–Alkyne Click Polymerization | 86 | ||
| 3.1 Introduction | 86 | ||
| 3.2 MFCP of Aroylacetylenes and Azides | 87 | ||
| 3.3 MFCP of Propiolates and Azides | 94 | ||
| 3.4 MFCP of Activated Azides and Alkynes | 104 | ||
| 3.5 Organobase-mediated MFCP of Azides and Alkynes | 111 | ||
| 3.6 Summary and Outlook | 113 | ||
| References | 114 | ||
| Chapter 4 - Catalyst-free Click Polymerization Using Nitrile N-Oxides Applicable to Various Dipolarophiles | 122 | ||
| 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 | ||
| Acknowledgements | 163 | ||
| References | 163 | ||
| Chapter 5 - Thiol-yne Click Polymerization | 167 | ||
| 5.1 Introduction | 167 | ||
| 5.2 General Mechanism | 168 | ||
| 5.2.1 Radical-initiated Thiol-yne Polymerization | 168 | ||
| 5.2.1.1 Initiation | 168 | ||
| 5.2.1.2 Propagation | 170 | ||
| 5.2.1.3 Termination | 171 | ||
| 5.2.2 Other Initiated Modes of TYCP | 171 | ||
| 5.3 Strategies of TYCP | 172 | ||
| 5.3.1 Radical-initiated TYCP | 172 | ||
| 5.3.1.1 Synthesis of Linear Sequence-controlled Polymers | 172 | ||
| 5.3.1.2 Synthesis of Dendritic and Hyperbranched Polymers | 175 | ||
| 5.3.1.3 Preparation of Polymeric Networks | 179 | ||
| 5.3.2 Transition Metal-catalyzed TYCP | 181 | ||
| 5.3.3 Amine-mediated TYCP | 183 | ||
| 5.3.4 Catalyst-free TYCP | 184 | ||
| 5.4 Applications | 185 | ||
| 5.4.1 High Refractive Index Materials | 185 | ||
| 5.4.2 Adsorbents for Metal Ions | 186 | ||
| 5.4.3 Drug Delivery | 186 | ||
| 5.4.4 Separation of Small Molecules | 186 | ||
| 5.4.5 Fabrication of 3D Materials | 187 | ||
| 5.4.6 Hybrid Materials for UV Nanoimprint Lithography | 187 | ||
| 5.5 Conclusions | 188 | ||
| References | 188 | ||
| Chapter 6 - Thiol-epoxy and Amine-epoxy ‘Click’ Polymerizations | 191 | ||
| 6.1 Introduction | 191 | ||
| 6.2 Discussion | 192 | ||
| 6.2.1 Thiol-epoxy ‘Click’ Polymerization | 194 | ||
| 6.2.2 Amine-epoxy ‘Click’ Polymerization | 200 | ||
| 6.3 Conclusions and Outlook | 201 | ||
| Acknowledgements | 204 | ||
| References | 204 | ||
| Chapter 7 - Multicomponent Polymerization Mediated by Click Chemistry | 207 | ||
| 7.1 Introduction | 207 | ||
| 7.2 Multicomponent Polymerization Based on Cu(i)-catalyzed MCR | 210 | ||
| 7.2.1 Multicomponent Polymerization of Alkynes, Sulfonyl Azides, and Amines | 210 | ||
| 7.2.2 Multicomponent Polymerization of Alkynes, Sulfonyl Azides, and Amino Esters | 213 | ||
| 7.2.3 Multicomponent Polymerization of Alkynes, Sulfonyl Azides, and Alcohols | 217 | ||
| 7.2.4 Multicomponent Polymerization of Alkynes, Sulfonyl Azides, H2O, and Alcohols | 218 | ||
| 7.2.5 Multicomponent Polymerization of Alkynes, Sulfonyl Azides, and Iminophosphorane | 221 | ||
| 7.2.6 Multicomponent Polymerization of Alkynes, Sulfonyl Azides, and Hydroxyacetophenone | 225 | ||
| 7.3 Macromolecular Engineering | 231 | ||
| 7.3.1 Post-polymerization Modification | 231 | ||
| 7.3.2 Multicomponent Tandem Polymerization | 231 | ||
| 7.3.3 Synthesis of Graft and Dendronized Polymers | 234 | ||
| 7.4 Conclusion | 236 | ||
| References | 239 | ||
| Subject Index | 244 |