Journal
ISCIENCE
Volume 25, Issue 9, Pages -Publisher
CELL PRESS
DOI: 10.1016/j.isci.2022.105020
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Funding
- National Science Foundation Grant (NSF EPSCoR Award) [IIA-1355466]
- United States Department of Agriculture (USDA-NIFA) [3TN372]
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A novel cyclobutane-containing diacid building block, CBDA-3, was synthesized using photocycloaddition and Fischer esterification. CBDA-3 has a unique semi-rigid character and excellent thermal stability, making it a promising sustainable alternative to traditional petroleum-derived diacids.
A novel cyclobutane-containing diacid building block, CBDA-3, was synthesized from sorbic acid using clean, efficient [2 + 2] photocycloaddition. This photoreac-tion 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 char-acteristics 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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