Cyclic imino ethers, such as oxazolines, have been extensively investigated as monomers for cationic ring opening polymerization, a living polymerization technique that enables access to polymers with controlled molecular weights and dispersities, as well as complex architectures such as block and graft copolymers. Polyoxazolines have found widespread applications in biomedical and materials fields, wherein the incorporation of various functional groups has expanded the properties of these polymers. The utilization of novel oxazolines, however, is fundamentally limited by incompatibility with the cationic mechanism of polymerization. We introduce an alkylthio-substituted oxazoline that undergoes living polymerization to give a polythiocarbamate, which upon oxidation can be quantitatively substituted with various nucleophiles such as amines and thiols. This divergent post-polymerization modification platform greatly broadens the scope of polyoxazoline functionality. The mild conditions allow the derivatization of block and graft copolymers with sensitive functionalities. Additionally, the polythiocarbamate is transformed in two steps into a guanidinium polyelectrolyte toward anion exchange membranes, with nanostructures obtainable from block and graft copolymerization.

Living polymerization of a 2-alkylthio-2-oxazoline as a divergent platform for post-polymerization functionalization

2019 Fall National Meeting

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