Anthranilamide-protected vinylboronic acid: rational monomer design for improved polymerization/transformation ability providing access to conventionally inaccessible copolymers† † Electronic supplementary information (ESI) available: Experimental and computational details, 1H and 13C NMR spectra, as well as computational results (PDF). See DOI: https://doi.org/10.1039/d2sc05094c

ABSTRACT: We have studied several protecting groups for vinylboronic-acid derivatives as monomers in radical polymerizations with the objective to improve the polymerization ability and C–B bond-cleaving post-transformation performance. Anthranilamide (aam)-protected vinylboronic acid (VBaam) exhibited experimentally a relatively high polymerization activity, which was theoretically corroborated by density functional theory (DFT) calculations that revealed a peculiar effect of the interaction between the aam groups on the polymerization behavior. The VBaam units in the copolymers can subsequently be transformed into vinyl alcohols or into ethylene units through C–B-bond-cleaving side-chain replacement, which affords valuable copolymers such as poly(vinyl alcohol-co-styrene), poly(ethylene-co-styrene

SUBMITTER: Suzuki H 

PROVIDER: S-EPMC9645380 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature