Radical polymerization by a supramolecular catalyst: Cyclodextrin with a RAFT reagent

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Abstract

Supramolecular catalysts have received a great deal of attention because they improve the selectivity and efficiency of reactions. Catalysts with host molecules exhibit specific reaction properties and recognize substrates via host-guest interactions. Here, we examined radical polymerization reactions with a chain transfer agent (CTA) that has α-cyclodextrin (α-CD) as a host molecule (α-CD-CTA). Prior to the polymerization of N,N-dimethylacrylamide (DMA), we investigated the complex formation of α-CD with DMA. Single X-ray analysis demonstrated that α-CD includes DMA inside its cavity. When DMA was polymerized in the presence of α-CD-CTA using 2,2'-azobis[2-(2-imidazolin-2-yl)propane dihydrochloride (VA-044) as an initiator in an aqueous solution, poly(DMA) was obtained in good yield and with narrow molecular weight distribution. In contrast, the polymerization of DMA without α-CD-CTA produced more widely distributed polymers. In the presence of 1,6-hexanediol (C6 diol) which works as a competitive molecule by being included in the α-CD cavity, the reaction yield was lower than that without C6 diol.

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Koyanagi, K., Takashima, Y., Nakamura, T., Yamaguchi, H., & Harada, A. (2016). Radical polymerization by a supramolecular catalyst: Cyclodextrin with a RAFT reagent. Beilstein Journal of Organic Chemistry, 12, 2495–2502. https://doi.org/10.3762/bjoc.12.244

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