Issue 63, 2022

A recyclable thermoset with built-in thermocleavable group developed from a cis-cyclobutane-1,2-dicarboxylic acid

Abstract

A novel class of recyclable thermoset has been developed from cis-3,4-diphenylcyclobutane-1,2-dicarboxylic acid (CBDA-4) due to its thermocleavability at high temperature. This key CBDA-4 building block was synthesized from β-trans-cinnamic acid using a [2+2] photocycloaddition reaction. CBDA-4 was subsequently linked with glycerol via esterification to give a thermoset with Tg of 68 °C. The thermoset was heated to 300 °C to analyze its degradation. A key intermediate was successfully obtained after purification of the degraded polymer. NMR, FT-IR, HRMS, and single crystal X-ray diffraction confirmed the intermediate was glycerol cinnamate, which was the result of splitting cyclobutane in the polymer backbone at high temperature. Glycerol cinnamate was readily hydrolyzed reforming the starting materials glycerol and trans-cinnamic acid to complete the recycling loop.

Graphical abstract: A recyclable thermoset with built-in thermocleavable group developed from a cis-cyclobutane-1,2-dicarboxylic acid

Supplementary files

Article information

Article type
Communication
Submitted
16 mar 2022
Accepted
05 júl 2022
First published
18 júl 2022

Chem. Commun., 2022,58, 8850-8853

Author version available

A recyclable thermoset with built-in thermocleavable group developed from a cis-cyclobutane-1,2-dicarboxylic acid

Z. Wang, H. Amjaour, J. E. M. Robertson, D. Azizov, A. Ugrinov and Q. R. Chu, Chem. Commun., 2022, 58, 8850 DOI: 10.1039/D2CC01502A

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