Organocatalytic/Metal-free Ring-opening Polymerization and Copolymerization of Epoxides

Ye Chen; Shan Liu; Jun-peng Zhao

doi:10.11777/j.issn1000-3304.2020.20088

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Organocatalytic/Metal-free Ring-opening Polymerization and Copolymerization of Epoxides

更新时间：2021-01-26

- Organocatalytic/Metal-free Ring-opening Polymerization and Copolymerization of Epoxides
- Acta Polymerica Sinica Vol. 51, Issue 10, Pages: 1067-1082(2020)
- 作者机构：
  
  华南理工大学材料科学与工程学院　广州 510640
- 作者简介：
- 基金信息：
- DOI：10.11777/j.issn1000-3304.2020.20088
  CLC：
- Published：1 September 2020，
  
  Published Online：16 July 2020，
  
  Received：27 March 2020，
  
  Revised：26 April 2020，
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Ye Chen, Shan Liu, Jun-peng Zhao. Organocatalytic/Metal-free Ring-opening Polymerization and Copolymerization of Epoxides. [J]. Acta Polymerica Sinica 51(10):1067-1082(2020)
DOI：

Ye Chen, Shan Liu, Jun-peng Zhao. Organocatalytic/Metal-free Ring-opening Polymerization and Copolymerization of Epoxides. [J]. Acta Polymerica Sinica 51(10):1067-1082(2020) DOI： 10.11777/j.issn1000-3304.2020.20088.

摘要

环氧化合物是高分子合成的基本原料和单体类型. 以环氧的开环反应为基础构建的杂链聚合物在性能上是碳链(烯烃类)聚合物的重要补充，在科学研究和国计民生的诸多领域具有广泛用途. 21世纪初以来，有机/无金属催化聚合获得了前所未有的快速发展，为环氧基聚合反应注入了新的活力. 尤其是近年来，Lewis酸碱型双组分无金属催化体系在该类聚合反应中展现出优异的催化效率和选择性，并且在环氧基高分子合成的简便化、绿色化、序列控制等方面实现了较大突破. 本文将介绍有机/无金属催化的环氧基聚合反应研究近况，主要包括环氧单体的均聚反应，环氧与非环氧类单体的无规、嵌段和交替共聚反应，以及基于环氧与环状酸酐交替共聚的一步法序列选择性嵌段共聚反应.

Abstract

Epoxide represents a major family of raw materials and monomers for heterochain polymers that have shown great utilities in academia

industry

and everyday lives. Typically

mega tons of ethylene oxide and propylene oxide are consumed annually

producing polyethers in the forms of homopolymers

statistical copolymers

block copolymers

etc

. Therefore

ring-opening (co)polymerization (ROP/ROCP) of epoxides and copolymerization of epoxides with non-epoxide (heterogenous) monomers have long been one critical topic in synthetic polymer chemistry. Since the beginning of 21

century

organocatalytic/metal-free polymerization has been a fast growing area of research

which has vigorously spurred on the long-established field of epoxide (co)polymerization. Strong organobases including phosphazene bases

-heterocyclic carbenes

and

-heterocyclic olefins constituted the first group of organocatalyst used to promote alcohol-initiated (oxy)anionic ROP of epoxides. In addition to controlling the molar mass and end-group functionality of polyethers

such endeavors also led to a series of new strategies

such as “catalyst switch”

for facile construction of epoxide-based heterogeneous copolymer structures. Mild non-nucleophilic organobases next stood out

showing good selectivity and control for epoxide-based alternating ROCP

due to a self-buffering mechanism based on proton shuttling between chain end and catalyst. The simple organobase also exhibited the capability in one-step synthesis of block copolyesters by sequence-selective terpolymerization of epoxide

cyclic anhydride

and cyclic ester that had been a filed long dominated by metallic catalysts. It was of great interests that some side reactions associated with organobases

such as macromolecular transesterification and oxygen-sulfur exchange

could be ingeniously utilized to develop new polymerization reactions and polymer synthesis methods. In very recent years

acid-base type two-component catalytic systems comprising a relatively mild organobase and a organoboron compound or a

-disubstituted (thio)urea have been prevailing because of the distinctly enhanced catalytic efficiency and chemoselectivity. In particular

organobase-triethylborane catalytic system showed strict selectivity for epoxide ROP over transesterification

which was attributed to a double-alkylborane-coordinated activated chain end mechanism. Therefore

a few long-standing challenges were well addressed

such as sequence-reversible block copolymerization of epoxide and cyclic ester

one-step synthesis of polyether monoester using carboxy initiators

etc

. The above-mentioned achievements and insights

among others

will be summarized.

关键词

环氧化合物开环聚合共聚反应有机催化聚合无金属聚合

Keywords

EpoxideRing-opening polymerizationCopolymerizationOrganocatalytic polymerizationMetal-free polymerization

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Key Laboratory of Biobased Polymer Materials, Shandong Provincial Education Department, College of Polymer Science and Engineering, Qingdao University of Science and Technology

State Key Laboratory Base of Eco-Chemical Engineering, College of Chemical Engineering

Beijing National Laboratory for Molecular Sciences, College of Chemistry and Molecular Engineering, Peking University, Key Laboratory of Polymer Chemistry and Physics of Ministry of Education

College of Chemical Engineering, Qingdao University of Science and Technology

Key Laboratory of Biobased Polymer Material, Shandong Provincial Education Department, College of Polymer Science and Engineering, Qingdao University of Science and Technology

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