Issue 37, 2021

Inspired by mussel adhesive protein: hydrophilic cationic copoly(2-oxazoline)s carrying catecholic side chains

Abstract

A set of new functionalized poly(2-oxazoline) homopolymers and copolymers carrying protected catecholic side chains were prepared by microwave-assisted cationic ring-opening (co)polymerization. The copolymerizations of 2-ethyl-2-oxazoline with either 2-(3,4-dimethoxyphenyl)-, 2-(3,4-dimethoxybenzyl)-, or 2-(3,4-dimethoxycinnamyl)-2-oxazoline (comonomer ratio 90 : 10) produced gradient or random copolymers with narrow molar mass distributions. During the copolymerization with the 2-(3,4-dimethoxycinnamyl)-2-oxazoline, however, chain coupling reactions occurred at monomer conversions of >50%, supposedly via Michael-type addition of intermediately formed ketene N,O-acetal end groups to 3,4-dimethoxycinnamyl amide side chains. A poly[(2-ethyl-2-oxazoline)-grad-(2-(3,4-dimethoxyphenyl)-2-oxazoline)] was examplarily subjected to partial demethylation and acidic hydrolysis to give a hydrophilic copolymer carrying both catecholic and cationic units, which is designed as a bioinspired adhesive copolymer mimicking mussel adhesive protein.

Graphical abstract: Inspired by mussel adhesive protein: hydrophilic cationic copoly(2-oxazoline)s carrying catecholic side chains

Supplementary files

Article information

Article type
Paper
Submitted
19 5 2021
Accepted
22 8 2021
First published
24 8 2021

Polym. Chem., 2021,12, 5310-5319

Inspired by mussel adhesive protein: hydrophilic cationic copoly(2-oxazoline)s carrying catecholic side chains

N. Lüdecke and H. Schlaad, Polym. Chem., 2021, 12, 5310 DOI: 10.1039/D1PY00679G

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