Controlled-Radical Polymerization of α-Lipoic Acid: A General Route to Degradable Vinyl Copolymers
Kaitlin R. Albanese, Parker T. Morris, Javier Read de Alaniz, Christopher M. Bates, Craig J. Hawker
Abstract
High Resolution Image Download MS PowerPoint Slide Here, we present the synthesis and characterization of statistical and block copolymers containing α-lipoic acid (LA) using reversible addition–fragmentation chain-transfer (RAFT) polymerization. LA, a readily available nutritional supplement, undergoes efficient radical ring-opening copolymerization with vinyl monomers in a controlled manner with predictable molecular weights and low molar-mass dispersities. Because lipoic acid diads present in the resulting copolymers include disulfide bonds, these materials efficiently and rapidly degrade when exposed to mild reducing agents such as tris(2-carboxyethyl)phosphine ( M n = 56 → 3.6 kg mol –1 ). This scalable and versatile polymerization method affords a facile way to synthesize degradable polymers with controlled architectures, molecular weights, and molar-mass dispersities from α-lipoic acid, a commercially available and renewable monomer.