Abstract
Polymeric materials modified with tertiary amino groups exhibit attractive properties for use in aqueous environments. Ring-opening metathesis polymerization (ROMP) is one of the versatile tools to synthesize functionalized polymers; however, the ROMP of monocyclic cycloolefins with tertiary amino groups is challenging because of the polymerization inhibition by the nitrogen atom coordination to the catalyst center. In this study, the ROMP of tertiary amino-functionalized monocyclic cycloolefins was first accomplished in high yield by utilizing the regioselective ROMP of 3-substituted cycloheptene (CHE) and cyclooctene (COE). This study suggests that the regioselective ROMP, which is achieved by the steric repulsion between the N-heterocyclic carbene ligand of the Grubbs second-generation catalyst and the functional group, might contribute to inhibit the coordination of donor functional groups to the Ru catalytic center, resulting in high monomer conversions. Head-to-tail regioregular polymers with tertiary amino side chains on every seventh and eighth backbone carbons, poly{3-[2-(N,N-dialkylamino)ethoxycarbonyl]-1-cycloolefin}s [P(3DR-CHE)s and P(3DR-COE)s, R = methyl and ethyl], were successfully synthesized. Hydrogenation that followed afforded the regioregular model linear poly[ethylene-co-2-(N,N-dialkylamino)ethyl acrylate] copolymers (alkyl = methyl and ethyl). The obtained novel amino-functionalized polymers exhibited unique behaviors in hydration, crystallization, and coating stability under physiological aqueous environment.
Published Version
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