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Living Polymerization of 2-Ethylthio-2-oxazoline and Postpolymerization Diversification.

ABSTRACT: The postpolymerization modification of polymers produced by living polymerization is an attractive method to create precision nanomaterials. We describe the living cationic ring-opening polymerization of a 2-alkylthio-2-oxazoline to furnish a polythiocarbamate. The polythiocarbamate is activated toward substitution by N- and S-nucleophiles via oxidation of the S to an SO₂. Mild substitution conditions provide broad functional group tolerance, constituting a versatile postpolymerization modification platform with access to a diversity of polyureas and polythiocarbamates. We further demonstrate the utility of this strategy by synthesizing and functionalizing block copolymers.

SUBMITTER: Wu YM

PROVIDER: S-EPMC6727665 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature

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Living Polymerization of 2-Ethylthio-2-oxazoline and Postpolymerization Diversification.

Wu You-Chi Mason YM Swager Timothy M TM

Journal of the American Chemical Society 20190731 32

The postpolymerization modification of polymers produced by living polymerization is an attractive method to create precision nanomaterials. We describe the living cationic ring-opening polymerization of a 2-alkylthio-2-oxazoline to furnish a polythiocarbamate. The polythiocarbamate is activated toward substitution by N- and S-nucleophiles via oxidation of the S to an SO2. Mild substitution conditions provide broad functional group tolerance, constituting a versatile pos ...[more]

PMID: 31365245

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