Ring-opening Polymerization of 2-Oxabicyclo[2.2.2]octan-3-one and the Influence of Stereochemistry on the Thermal Properties of the Polyesters

Tong Zhou; Yu-Ting Guo; Fu-Sheng Du; Zi-Chen Li

doi:10.1007/s10118-022-2725-1

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Ring-opening Polymerization of 2-Oxabicyclo[2.2.2]octan-3-one and the Influence of Stereochemistry on the Thermal Properties of the Polyesters

RESEARCH ARTICLE | Updated：2022-09-23

- Ring-opening Polymerization of 2-Oxabicyclo[2.2.2]octan-3-one and the Influence of Stereochemistry on the Thermal Properties of the Polyesters
- Chinese Journal of Polymer Science Vol. 40, Issue 10, Pages: 1173-1182(2022)
- Affiliations：
  
  1.Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polym. Chem. & Physics of Ministry of Education, Department of Polymer Science & Engineering, College of Chemistry and Molecular Engineering, Center for Soft Matter Science and Engineering, Peking University, Beijing 100871, China
- Author bio：
  
  fsdu@pku.edu.cn (F.S.D.)
  zcli@pku.edu.cn (Z.C.L.)
- Funds：
- DOI：10.1007/s10118-022-2725-1
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Tong Zhou, Yu-Ting Guo, Fu-Sheng Du, et al. Ring-opening Polymerization of 2-Oxabicyclo[2.2.2]octan-3-one and the Influence of Stereochemistry on the Thermal Properties of the Polyesters. [J]. Chinese Journal of Polymer Science 40(10):1173-1182(2022)
DOI：

Tong Zhou, Yu-Ting Guo, Fu-Sheng Du, et al. Ring-opening Polymerization of 2-Oxabicyclo[2.2.2]octan-3-one and the Influence of Stereochemistry on the Thermal Properties of the Polyesters. [J]. Chinese Journal of Polymer Science 40(10):1173-1182(2022) DOI： 10.1007/s10118-022-2725-1.

摘要

ROP of a bicyclic lactone, 2-oxabicyclo[2.2.2]octan-3-one ,([2.2.2]VL,), was systematically investigated under different conditions to obtain a series of ,P[2.2.2]VL,s with variable stereochemistry. The ,cis, to ,trans, isomerization mechanism under strong basic conditions was elucidated together with the effect of stereochemistry on the polymer properties.

Abstract

Polyesters with cyclic structures in the main chain typically possess superior mechanical and thermal properties together with chemical recyclability. Ring-opening polymerization (ROP) of bridged or fused bicyclic lactones is a simple, and in most cases controlled method to synthesize polyesters with alicyclic moieties in the polymer backbone. The stereochemistry of the alicyclic structures has a great effect on the polymer properties, which can be regulated by varying the polymerization conditions. Here, we report a systematic investigation on the ROP of 2-oxabicyclo[2.2.2]octan-3-one (,[2.2.2]VL,) under different conditions. When initiated by ,n,-butyl lithium (,n,-BuLi) or catalyzed by trifluoromethanesulfonic acid (TfOH) in the presence of benzyl alcohol,P[2.2.2]VLs, containing all ,cis,-1,4 disubstituted cyclohexane ring were obtained. However,P[2.2.2]VLs, initiated by sodium methoxide (MeONa) or catalyzed by organic superbase contained both ,cis, and ,trans, isomeric structural units. The ,cis, to ,trans, transformation mechanism under these conditions was manifested, and the effect of stereochemical variations on the properties of ,P[2.2.2]VL, was revealed. The stereoregular ,P[2.2.2]VLs, both ,cis, and ,trans, exhibited higher crystallinity and melting temperatures (,T,m,) than those of the stereoirregular isomers. Finally, the degradation of ,P[2.2.2]VL, with acid at high temperature could recover 3-cyclohexenecarboxylic acid.

关键词

Keywords

2-Oxabicyclo[2.2.2]octan-3-oneRing-opening polymerizationStereochemistryPolyesterThermal properties

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