title: Synthesis and click chemistry of a new class of biodegradable polylactide towards tunable thermo-responsive biomaterials.
abstract: A new class of clickable and biodegradable polylactide was designed and preparedviabulk polymerization of 3,6-dipropargyloxymethyl-1,4-dioxane-2,5-dione (1) which was synthesized from easily accessible propargyloxylactic acid (5). A homopolymer of1and random copolymer of1with l-lactide were obtained as amorphous materials and exhibit lowTgof 8.5 and 34 °C, respectively, indicating their promising potentials for biomedical applications. The statistical nature of random copolymers was investigated by DSC analysis and13C 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 mannerviaclick chemistry.
authors: Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA.
authors: Quanxuan
authors: Q
authors: Zhang
authors: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA ; Athinoula A. Martinos Center for Biomedical Imaging, Department of Radiology, Massachusetts General Hospital, Harvard Medical School, Charlestown, MA 02129, USA.
authors: Hong
authors: H
authors: Ren
authors: Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA.
authors: Gregory L
authors: GL
authors: Baker