Regioselective Polymerization of <italic style="font-style: italic">α</italic>-Methylene <italic style="font-style: italic">β</italic>-Butyrolactone: Synthesis of Linear and Cyclic Polyesters

Yue-chao Xu; Hui Zhou; Xiao-bing Lu

doi:10.11777/j.issn1000-3304.2020.19145

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Regioselective Polymerization of α-Methylene β-Butyrolactone: Synthesis of Linear and Cyclic Polyesters

更新时间：2021-04-27

- Regioselective Polymerization of α-Methylene β-Butyrolactone: Synthesis of Linear and Cyclic Polyesters
- Acta Polymerica Sinica Vol. 51, Issue 1, Pages: 91-97(2020)
- 作者机构：
  
  精细化工国家重点实验室大连理工大学　大连 116024
- 作者简介：
- 基金信息：
- DOI：10.11777/j.issn1000-3304.2020.19145
  CLC：
- Published：2020-1，
  
  Published Online：27 September 2019，
  
  Received：2 August 2019，
  
  Revised：20 August 2019，
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Yue-chao Xu, Hui Zhou, Xiao-bing Lu. Regioselective Polymerization of α-Methylene β-Butyrolactone: Synthesis of Linear and Cyclic Polyesters. [J]. Acta Polymerica Sinica 51(1):91-97(2020)
DOI：

Yue-chao Xu, Hui Zhou, Xiao-bing Lu. Regioselective Polymerization of α-Methylene β-Butyrolactone: Synthesis of Linear and Cyclic Polyesters. [J]. Acta Polymerica Sinica 51(1):91-97(2020) DOI： 10.11777/j.issn1000-3304.2020.19145.

摘要

设计不同的催化体系或引发剂实现了

-亚甲基-

-丁内酯(M

BL)单体的区域选择性聚合，合成不同拓扑结构的聚酯. 选用偶氮二异丁腈(AIBN)自由基引发剂，选择性聚合M

BL的

位上亚乙烯基双键，形成线形含有四元环内酯单元的聚酯. 使用SalenAlCH

金属配合物催化剂，区域选择性在M

BL的酰-氧键断裂，生成双键保留以间同结构为主的结晶性线形聚酯. 有机强碱是M

BL的高效开环聚合催化剂，获得以酰-氧键断裂为主的线形聚酯. 而使用简单碘化钠催化M

BL开环聚合，形成以烷-氧键断裂为主的结晶性环状聚酯.

Abstract

Regioselective polymerization of

-methylene

-butyrolactone (M

BL) to afford polyesters with various topological structures was achieved by the use of different catalysts or initiators. With azodiisobutyronitrile (AIBN) as initiator

polymerization selectively occurred at the C＝C bond to produce linear poly(

-methylene-

-butyrolactone) (PM

BL) with the remain of

-butyrolactone unit. Achiral Salen aluminum complexes afforded linear syndiotactic-enriched polyesters with controllable molecular weight and a narrow polydispersity

in which ring-opening polymerization selectively occurred at the acyl C―O bond of M

BL and the C＝C bond was remained. Strong organic bases

such as 1

8-diazabicyclo[5.4.0]undec-7-ene (DBU)

exhibited high activity for ring-opening polymerization of M

BL under mild condition

affording linear polyesters. Simple sodium iodide mediated M

BL polymerization predominately produced crystalline cyclic polyesters with a melting point of 145.4 °C

in which the ring-opening mainly concerned the alkyl C

―O bond cleavage. This study demonstrates that the synthesis of various topological materials with different properties can be achieved by regioselective polymerization of functional monomers with the exquisite choice of catalyst or initiator.

关键词

α-亚甲基-β-丁内酯聚酯开环聚合区域选择性环状聚合物

Keywords

α-Methylene β-butyrolactonePolyesterRing-opening polymerizationRegioselectivityCyclic polymer

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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

Collgene of Chemical Engineering, Qingdao University of Science and Technology

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

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Regioselective Polymerization of α-Methylene β-Butyrolactone: Synthesis of Linear and Cyclic Polyesters

DOI：10.11777/j.issn1000-3304.2020.19145

摘要

Abstract

关键词

Keywords

references