Synthesis of Thermo-Responsive Monofunctionalized Diblock Copolymer Worms

Overview

Journal Polymers (Basel)

Publisher MDPI

Date 2024 Jan 17

PMID 38231987

Authors

Xuan Xue

Feifei Wang

Minhao Shi

Faez Iqbal Khan

Affiliations

Soon will be listed here.

Abstract

Poly(glycerol monomethacrylate)--poly(2-hydroxypropyl methacrylate) (PGMA-PHPMA) with worm-like morphology is a typical example of reversible addition-fragmentation chain transfer (RAFT) dispersion polymerized thermo-responsive copolymer via polymerization-induced self-assembly (PISA) in aqueous solution. Chain transfer agents (CTAs) are the key component in controlling RAFT, the structures of which determine the end functional groups of the polymer chain. It is therefore of interest to monofunctionalize the polymers via CTA moiety, for bioactive functionality conjugation and in the meantime maintain the precisely controlled morphology of the copolymers and the related property. In this work, a newly designed CTA 5-(2-(-butoxycarbonylamino) ethylamino)-2-cyano-5-oxopentan-2-yl benzodithioate CPDB) was synthesized and used for the RAFT polymerization of PGMA-PHPMA. Subsequently, PGMA-PHPMA copolymers with primary amine, maleimide, and reduced L-glutathione (a tripeptide) monofunctionalized terminals were synthesized via deprotection and conjugation reactions. These monofunctionalized copolymers maintain worm-like morphology and thermo-responsive property in aqueous solution (10% /), as confirmed by the transmission electron microscopy (TEM) images, and the observation of the phase transition behavior in between 4 °C and room temperature (~20 °C), respectively. Summarily, a range of thermo-responsive monofunctionalized PGMA-PHPMA diblock copolymer worms were successfully synthesized, which are expected to offer potential biomedical applications, such as in polymer therapeutics, drug delivery, and diagnostics.

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