Chiral Resolution of Racemic (±)-1,1'Bi (2-Naphthol) by Use of Molecularly Imprinted Polymers

Abstract

Polymers imprinted with (S)-(-)-1,1’-bi (2-naphthol) and (R)-(+)-1,1’-bi (2-naphthol) have been prepared by non-covalent imprinting. A combinational procedure was used to optimize the functional monomer and crosslinker. A copolymer of 2-vinylpyridine and divinylbenzene resulted in the best chiral recognition. The ratio of template to functional monomer and solvent in the pre-polymerization mixture were also optimized. The imprinted polymers were used as stationary phases in high-performance liquid chromatography (HPLC). The molecularly imprinted polymers (MIPs) were more selective when prepared using a less polar solvent. Effective separations of the enantiomers of racemic (±)-1, 1’-Bi (2-naphthol) were achieved by use of acetonitrile as mobile phase; no cross-selectivity was observed. Interactions between functional monomers and template were investigated by 1H NMR spectroscopy. The results suggest that hydrogen-bonding between the functional monomer and the template and π-π stacking interaction between the cross-linker and the template may contribute to chiral recognition.