Synthesis of Multifunctional Homopolymers through Using Thiazolidine Chemistry and Post-Polymerization Modification

Abstract

Multifunctional homopolymers, defined here as polymers that contain multiple reactive functional groups per repeat unit, are versatile scaffolds for preparing complex macromolecules via post-polymerization modification. However, there are limited methods for preparing multifunctional homopolymers that contain more than one nucleophilic site per repeat unit. Herein, a strategy to synthesize a multifunctional homopolymer using thiazolidine chemistry is demonstrated. Controlled radical polymerization of a thiazolidine-containing acrylamido monomer allows for the synthesis of a polymer with pendent latent nucleophiles. Ring-opening of the thiazolidine affords a homopolymer with two side-chain reactive sites, an amine and a thiol. One-pot functionalization via disulfide formation and acyl substitution is performed to introduce two distinct groups in each repeat unit.

Keywords: multifunctional homopolymers; post-polymerization modification; reversible addition-fragmentation chain transfer polymerization; thiazolidine.