Almost optically pure (+)- and (-)-2-fluorophenyl-4-fluorophenyl-2-pyridylmethyl methacrylate (2F4F2PyMA) monomers were obtained by HPLC resolution of the racemic monomer and polymerized with the use of anionic and free-radical initiators. Helix-sense selectivity during the polymerization seemed to be governed mainly by the chirality of the monomer itself, and the polymers obtained by using the complex of N,N'-diphenylethylenediamine monolithium amide with(S)-(+)-1-(2-pyrrolidinylmethyl)-pyrrolidine (PMP) in toluene at -78 degrees C appeared to possess single-handed helical conformation (+)-poly[(-)-2F4F2PyMA], [alpha](365) + 1510 degrees; (-)-poly[(+)-2F4F2PyMA], [alpha](365) - 1610 degrees]. The single-handed helical (+)-poly[(-)-2F4F2PyMA] and (-)-poly[(+)-2F4F2PyM] obtained with the PMP complex exhibited better chiral recognition ability toward trans-stilbene oxide compared with the single-handed helical poly(rac-2F4F2PyMA) prepared previously.