A Facile Synthesis of Cyclic Macromonomer via Sulfoxide-based Vinyl Protection
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We report an efficient method to synthesize vinyl-containing cyclic macromonomer via sulfoxide chemistry. Considering the low yield of cyclic products, this new route for functionalized cyclic structures without additional steps to attach the monomer site is important. This latent vinyl site enables the cyclic polymer to act freely as a macromer in radical polymerization and play an essential role in introducing cyclic moieties in macrostructure. For this, novel multi-functional ATRP initiator with three different functional characteristics was newly designed; alkyl halide, terminal alkyne with silyl protected group, and sulfoxide-protected methacrylate moiety. Initially, the halide was utilized as the initiator of atom transfer radical polymerization (ATRP), followed by the azidation of the halide chain end. After deprotection of silane, the alkyne was clicked with the azide via azide-alkyne cycloaddition (CuAAC). The cyclic structure was confirmed using SEC, 1H NMR, and MALDI-TOF. This approach allows precise control of the cyclic side group for a unique class of cyclic topologies.