Journal
POLYMER CHEMISTRY
Volume 6, Issue 8, Pages 1275-1285Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4py01425a
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Funding
- NIH [5RC2ES018756-02]
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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 T-g of 8.5 and 34 degrees C, respectively, indicating their promising potentials for biomedical applications. The statistical nature of random copolymers was investigated by DSC analysis and C-13 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 degrees 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.
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