Synthesis of a symmetrically meta-substituted poly(diphenylacetylene) bearing chiral amide groups and its application as a chiral stationary phase for high-performance liquid chromatography

Abstract

Abstract A symmetrically meta-substituted poly(diphenylacetylene) bearing chiral amide groups was synthesized by reacting (R)-1-phenylethylamine with a carboxy-group-containing precursor polymer, which was obtained by polymerizing the corresponding ester-containing diphenylacetylene using a modified Mo(V)-based catalytic system followed by hydrolysis. The polymer formed a one-handed helical conformation when thermally annealed in a solvent. The chiral recognition ability of the polymer before and after thermal annealing was investigated when used as a chiral stationary phase for high-performance liquid chromatography.