Simple and Efficient Approach toward Photosensitive Biobased Aliphatic Polycarbonate Materials

Fatty acids were used as precursors for the synthesis of photosensitive polycarbonate materials. In order to avoid multistep reactions, a simple and straightforward methodology toward the synthesis of photosensitive monomers has been developed. Hence, a fatty acid-based cyclic carbonate bearing an unsaturation was synthesized and subsequently polymerized in a controlled manner (Đ = 1.07) by organo-catalyzed ring-opening polymerization (ROP). A thio-cinnamate derivative was then readily synthesized via a one-pot reaction and grafted onto the polycarbonate backbone by thiol-ene reaction. The content of photoresponsive cinnamoyl moiety grafted on the polycarbonate was tunable with the reaction time. Such functionalized polycarbonates could be crosslinked (by UV irradiation at 365 nm) and partially decrosslinked (irradiated at 254 nm) and exhibit versatile properties ranging from rather tough materials to elastomeric networks with respect to the content of the photosensitive cinnamoyl moiety grafted on the polymer.