A contemporary challenge facing most applications of polymers relates to sustainability and scalability. The key building block in my research is α-lipoic acid, a natural, biocompatible, and commercially available antioxidant found in various consumer supplements. α-Lipoic acid
features a saturated 1,2-dithiolane ring that undergoes radical ring-opening polymerization in the presence of UV light, heat, or radical initiators, resulting in dynamic and degradable disulfide bonds. I will discuss different synthetic approaches using α-lipoic acid and related dithiolanes to transform otherwise persistent plastics into degradable and recyclable materials.
In addition, I will present the synthesis and characterization of random copolymers containing 1,2-dithiane — a six-membered disulfide-containing heterocycle — under traditional free radical conditions. The reduced ring strain of 1,2-dithiane facilitates efficient radical ring-opening polymerization with less activated monomers such as vinyl acetate. This strategy is an elegant example to expand the scope of degradable building blocks through strategic monomer design.