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Controlling Polymer Microstructure and Degradation with Cyclic Thiocarbonyl Monomers

1. Impact of Research The central goal of this project is to identify cyclic thiocarbonyl molecules that are capable of efficient copolymerization with common petroleum-derived monomers (styrene, acrylates, acrylamides). Given the privileged nature of thiocarbonyl moieties as radical acceptors, it was proposed that this reactivity could be leveraged to generate a new platform for radical ring-opening polymerization (rROP) in which thioester functionality is introduced into the polymer backbone (Figure 1). If successfully used as a comonomer with petroleum-derived monomer families, these additives could serve as hydrolytically labile points on a polymer chain to produce value-added responsive and degradable materials. Our studies over the past year have focused on identifying molecules that feature a Z-group capable of stabilizing the radical intermediate in the ring-opening process, along with installing R-type functionality that lead to low energy radicals compatible with living reversible deactivation polymerization methods.