iScience (Sep 2022)

A biorenewable cyclobutane-containing building block synthesized from sorbic acid using photoenergy

  • Micah Mabin,
  • Quintin Elliott,
  • Zhihan Wang,
  • Angel Ugrinov,
  • Qianli R. Chu

DOI
https://doi.org/10.1016/j.isci.2022.105020
Journal volume & issue
Vol. 25, no. 9
p. 105020

Abstract

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Summary: A novel cyclobutane-containing diacid building block, CBDA-3, was synthesized from sorbic acid using clean, efficient [2 + 2] photocycloaddition. This photoreaction can be performed using commercially available germicidal lamps, which represent a form of ECO-UV. SC-XRD showed that the cyclobutane ring in CBDA-3 has a unique semi-rigid character, unlike more rigid aromatic rings or more flexible types of aliphatic rings. C=C bonds present in the structure of CBDA-3 provide opportunities for derivatization which could be used to alter the characteristics of polymers made from this monomer. Additionally, TGA and DSC analysis showed CBDA-3 to have excellent thermal stability. These characteristics make CBDA-3 a promising building block with the potential to be used as a sustainable alternative to traditional petroleum-derived diacids. Finally, a facile and reliable Fischer esterification of CBDA-3 was performed to tune its melting point and solubility for different applications and to demonstrate the applicability of this building block in polymer synthesis.

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