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Three-Component Dynamic Covalent Chemistry: From Janus Small Molecules to Functional Polymers

Hongxu Liu, Hung‐Hsun Lu, Jiaming Zhuang, S. Thayumanavan

2021Journal of the American Chemical Society26 citationsDOI

Abstract

ercaptobenzaldehyde (HAM reaction) has been developed and applied to multicomponent polymerization and controlled radical polymerization for the construction of random and block copolymers. This chemistry features mild reaction conditions, high yield, simple isolation, and water as the only byproduct. With the advantages of the distinct nucleophilicity of thiol and hydroxyl groups, the chemistry could be used for stepwise labeling and modifications on primary amines. The Janus chemical joint formed from this reaction exhibits degradability in buffers and generates the corresponding starting reagents, allowing amine release. Interestingly, the chemical joint exhibits thermally activated reversibility with water as the catalyst. This multicomponent dynamic covalent feature has been applied to the metamorphosis of random and block copolymers, generating polymers with diverse architectures. This chemistry is expected to be broadly applicable to synthetic polymer chemistry and materials science.

Topics & Concepts

ChemistryPolymerizationPolymerCovalent bondCopolymerNucleophileReagentDynamic covalent chemistryAmine gas treatingPolymer chemistryJanusMoleculeOrganic chemistryCombinatorial chemistryCatalysisNanotechnologySupramolecular chemistryMaterials scienceAdvanced Polymer Synthesis and CharacterizationSynthetic Organic Chemistry MethodsPolymer composites and self-healing
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