Asymmetric polymerization of diphenyl-3-pyridylmethyl methacrylate leading to optically active polymer with helical conformation and chiral recognition ability of the polymer

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 degrees 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 degrees C also gave an isotactic polymer (mm similar to 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).