Journal
CHEMICAL SCIENCE
Volume 13, Issue 43, Pages 12703-12712Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2sc05094c
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Funding
- JSPS KAKENHI [19K15622, 22K14724, 17H06453, 19H00911, 20K21222]
- Kyoto Technoscience Center
- Hattori Hokokai Foundation
- Tokuyama Science Foundation
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The effect of protecting groups on the polymerization of vinylboronic-acid derivatives has been studied, and it has been found that anthranilamide-protected vinylboronic acid exhibits high polymerization activity and post-transformation capability.
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).
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