We report successful synthesis of 3-trifluoromethyl-6-methyl-1,4-dioxane-2,5-dione and ring opening polymerization of the new fluoro-lactide monomer to prepare polylactides composed of trifluoromethyl and methyl pendent groups on each repeat unit (FPLA). Molecular weights of the prepared polymers correlated well with the initial molar ratio of monomer to initiator, and were found to range from 6.6 to 22.5 kDa as determined by 1H NMR spectroscopy. 1H, 13C, and 19F NMR spectroscopy were consistent with the structures of the lactide monomer isomers, and 1H NMR analysis was consistent with polymer backbones of alternating trifluoromethyl- and methyl-substituted lactate constituents. Additionally, we prepared amphiphilic block copolymers of FPLA and PEG (FPLA-b-PEG diblocks and FPLA-PEG-FPLA triblocks) by using methoxy PEG (mPEG) or PEG as alcohol initiators. We observed the formation of vesicles or worm-like micelles from the particles of FPLA-PEG-FPLA in dilute aqueous solution by TEM, suggesting potential applications for drug delivery.

Facile synthesis of fluorine-substituted polylactides and self-assembly of their amphiphilic block copolymers in solution

256th National Meeting (2018)

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