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

Micah Mabin; Quintin Elliott; Zhihan Wang; Angel Ugrinov; Qianli R Chu

doi:10.1016/j.isci.2022.105020

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

iScience. 2022 Aug 27;25(9):105020. doi: 10.1016/j.isci.2022.105020. eCollection 2022 Sep 16.

Authors

Micah Mabin¹, Quintin Elliott¹, Zhihan Wang¹, Angel Ugrinov², Qianli R Chu¹

Affiliations

¹ Department of Chemistry, University of North Dakota, Grand Forks, ND 58202, USA.
² Department of Chemistry and Biochemistry, North Dakota State University, Fargo, ND 58102, USA.

Abstract

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.

Keywords: Chemistry; green chemistry; organic chemistry.