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 alternating 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.

Facile synthesis of fluorine-substituted, alternating polylactides and their amphiphilic block copolymers

255th National Meeting (2018)

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