Issue 43, 2022

Anthranilamide-protected vinylboronic acid: rational monomer design for improved polymerization/transformation ability providing access to conventionally inaccessible copolymers

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), and poly(ethylene-co-acrylate).

Graphical abstract: Anthranilamide-protected vinylboronic acid: rational monomer design for improved polymerization/transformation ability providing access to conventionally inaccessible copolymers

Supplementary files

Article information

Article type
Edge Article
Submitted
13 Sep 2022
Accepted
18 Okt 2022
First published
18 Okt 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2022,13, 12703-12712

Anthranilamide-protected vinylboronic acid: rational monomer design for improved polymerization/transformation ability providing access to conventionally inaccessible copolymers

H. Suzuki, T. Nishikawa, H. Makino and M. Ouchi, Chem. Sci., 2022, 13, 12703 DOI: 10.1039/D2SC05094C

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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