Synthesis and click chemistry of a new class of biodegradable polylactide towards tunable thermo-responsive biomaterials

Quanxuan Zhang, Hong Ren, Gregory L. Baker

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

A new class of clickable and biodegradable polylactide was designed and prepared via bulk polymerization of 3,6-dipropargyloxymethyl-1,4-dioxane-2,5-dione (1) which was synthesized from easily accessible propargyloxylactic acid (5). A homopolymer of 1 and random copolymer of 1 with l-lactide were obtained as amorphous materials and exhibit low Tg of 8.5 and 34 °C, respectively, indicating their promising potentials for biomedical applications. The statistical nature of random copolymers was investigated by DSC analysis and 13C NMR spectroscopy, which implies the random distribution of terminal alkyne groups along the back bone of copolymers. The efficient click post-modification of this new class of polylactide with alkyl and mPEG azides affords novel hydrophilic biomaterials, which exhibit reversible thermo-responsive properties as evidenced by their tunable LCST ranging from 22 to 69 °C depending on the balance of the incorporated hydrophilic/hydrophobic side chains. These results indicate the generality of this new class of clickable polylactide in preparing novel smart biomaterials in a simple and efficient manner via click chemistry. This journal is

Original languageEnglish (US)
Pages (from-to)1275-1285
Number of pages11
JournalPolymer Chemistry
Volume6
Issue number8
DOIs
StatePublished - Feb 28 2015

Bibliographical note

Publisher Copyright:
© The Royal Society of Chemistry.

Copyright:
Copyright 2017 Elsevier B.V., All rights reserved.

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