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
- 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 2022年40卷第10期页码：1173-1182
- Affiliations：
  
  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：
  
  This work was financially supported by the National Natural Science Foundation of China (Nos. 21871014 and 21971005).;Electronic supplementary information (ESI) is available free of charge in the online version of this article at http://doi.org/10.1007/s10118-022-2725-1.
- DOI：10.1007/s10118-022-2725-1
  中图分类号：
- 收稿：2022-01-22，
  
  修回：2022-2-24，
  
  录用：2022-2-27，
  
  网络首发：2022-06-06，
  
  纸质出版：2022-10-01
- Accepted：
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Zhou, T.; Guo, Y. T.; Du, F. S.; Li, Z. C. 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 J. Polym. Sci. 2022, 40, 1173–1182

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, 2022, 40(10): 1173-1182.
Zhou, T.; Guo, Y. T.; Du, F. S.; Li, Z. C. 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 J. Polym. Sci. 2022, 40, 1173–1182 DOI： 10.1007/s10118-022-2725-1.

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, 2022, 40(10): 1173-1182. 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

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

-butyl lithium (

-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

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 (

) 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

references

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