Enantioseparation on poly(phenyl isocyanide)s with macromolecular helicity memory as chiral stationary phases for HPLC

Abstract

A series of novel optically active poly(phenyl isocyanide)s bearing achiral benzanilide pendant groups was prepared based on the noncovalent “helicity induction and memory strategy”. The polymers that exhibited an optical activity due to the macromolecular helicity memory were immobilized to 3-aminopropyl-silanized silica gel through chemical bonding or coated on the silica gel to obtain chiral packing materials for high-performance liquid chromatography (HPLC). The chiral recognition abilities toward a variety of racemic compounds with different functionalities were investigated by HPLC. The obtained CSPs separated various racemates into enantiomers, in particular, a right-handed helical poly(phenyl isocyanide) carrying achiral anilide pendants showed an excellent chiral recognition ability and completely or partially resolved nine racemates, including cyclic ether, amine, ketones and metal acetylacetonate complexes, among twelve racemates.