A cis-3,4-di(furan-2-yl)cyclobutane-1,2-dicarboxylic
acid (CBDA-2) is readily prepared stereospecifically
from trans-3-(2-furyl)acrylic acid, a furfural-derived
compound, through a solid-state [2 + 2] photocycloaddition in 95%
isolated yield. The cyclobutane ring in CBDA-2 shows
desired stabilities during thermal, sunlight, and chemical tests.
The single crystal structure of CBDA-2 revealed the geometry
of this molecule and orientation of the two dicarboxylic acid groups
displaying its potential to serve as a unique, semirigid diacid building
block in material science. A preliminary study showed that condensation
of this diacid with glycerol yielded a green polymer with good stability.
The diacid could also be used as a cross-linker for a biobased epoxy
to yield an exceptionally hard and solvent-resistant thermoset.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.