Abstract
Diphenyl-3-pyridylmethyl methacrylate was synthesized and polymerized using the complexes of N,N′-diphenylethylenediamine monolithium amide with (+)-1-(2-pyrrolidinylmethyl)pyrrolidine, (+)-2,3-dimethoxy-1,4-bis(dimethylamino)butane, and (−)-sparteine in toluene at −78°C (helix-sense-selective polymerization). The obtained polymers were highly isotactic and exhibited large dextrorotation based on helical conformation with excess single-handed helicity. Free radical polymerization with (iso-PrOCOO)2 in toluene at 40°C also gave an isotactic polymer (mm∼74%). The optically active polymer exhibited chiral recognition ability toward several racemic compounds including hexahelicene, trans-stilbene oxide, and binaphthyl derivatives when adsorbed on macro porous silica gel and used as a stationary phase for high-performance liquid chromatography (HPLC).
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Nakano, T., Taniguchi, K. & Okamoto, Y. Asymmetric Polymerization of Diphenyl-3-pyridylmethyl Methacrylate Leading to Optically Active Polymer with Helical Conformation and Chiral Recognition Ability of the Polymer. Polym J 29, 540–544 (1997). https://doi.org/10.1295/polymj.29.540
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DOI: https://doi.org/10.1295/polymj.29.540