Chromatographia

, Volume 65, Issue 11, pp 675–679

Chiral Resolution of Racemic 4-Phenyl(benzyl)-2-Oxazolidone by Use of Molecularly Imprinted Polymers

Original

DOI: 10.1365/s10337-007-0209-7

Cite this article as:
Luo, Y., Liu, L., Li, L. et al. Chroma (2007) 65: 675. doi:10.1365/s10337-007-0209-7

Abstract

Polymers imprinted with (S)-4-phenyl-2-oxazolidone and (S)-4-benzyl-2-oxazolidone have been prepared by non-covalent imprinting. A combinational procedure was used to optimize the functional monomer and crosslinker. A copolymer of methacrylic acid 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. The MIPs were more selective when prepared using a less polar solvent, except for toluene. Effective separations of the enantiomers of racemic 4-phenyl-2-oxazolidone and 4-benzyl-2-oxazolidone 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.

Keywords

Column liquid chromatography1H NMRMolecularly imprinted polymers4-Phenyl-2-oxazolidone

Copyright information

© Friedr. Vieweg & Sohn Verlag/GWV Fachverlage GmbH 2007

Authors and Affiliations

  1. 1.School of Chemistry and Chemical EngineeringSun Yat-Sen UniversityGuangzhouChina