Synthesis of Carboxylic Acid Bearing Polyethers by Monomer-Activated Anionic Ring-Opening Polymerization
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We report a novel epoxide monomer, tert-butylglycidoxy acetate (tBGA) in this study. While the conventional anionic ring-opening polymerization does not provide a controlled synthesis of poly(tert-butylglycidoxy acetate) (PtBGA) due to the undesirable side reactions, the monomer-activated anionic ring-opening polymerization (MAROP) of a tBGA monomer, using tetrabutylammonium iodide as an initiator and triisobutylaluminum, Al(iBu)3, as an activator affords the controlled polymerizations. Subsequent acidic deprotection of PtBGA yielded the corresponding polymers (PGA) with a large number of carboxylic acid functionality along the polyether backbone. Interestingly, the pH-dependent self-association based on the hydrogen bonding between the carboxylic acid groups was observed, leading to the formation of pH-responsive hydrogels. With its superior biocompatibility of PtBGA and PGA, we anticipate the prospective potentials for the applications in biological and biomedical fields.