Ring-Opening Polymerization of Imidazole Epoxides for the Synthesis of Imidazole-Substituted Poly(ethylene oxides)

The synthesis and polymerization of imidazole-substituted epoxides, a novel family of monomers and polymers, for potential incorporation into polymeric therapeutics, ion- transport membranes, and catalysis/metal coordination has been reported. Imidazole-substituted epoxide monomers, l-tritylimidazole-2- ethylene oxide (TTm-2-EO) and l-tritylimidazole-4-ethylene oxide (TTm-4-EO), were prepared using a three-step and two-step synthetic approach starting from imidazole (Tm) or imidazole-4-car- boxaldehyde (Tm-4-ca). The ability to tune molecular weight, topology, architecture, and functionality has catalyzed the discovery of biocompatible polymers for emerging biomedical technologies. The polymerization reactions were initially yellow, heterogeneous solutions that became homogeneous as polymerization progressed. Novel imidazole-substituted epoxide monomers were successfully synthesized and polymerized using anionic ROP.