Preparation and enantioseparation characteristics of a novel chiral stationary phase based on mono (6A-azido-6A-deoxy)-per(p-chlorophenylcarbamoylated) β-cyclodextrin

A novel cyclodextrin (CD) derivative-mono (6(A)-azido-6(A)-deoxy)-per(p-chlorophenylcarbamoylated) beta-CD was synthesized and chemically immobilized onto the surface of amino-functionalized silica gel to afford a structurally well-defined chiral stationary phase (CSP) for high performance liquid chromatography (HPLC). The p-chlorophenyl groups introduced on the beta-CD are pi-electron deficient (i.e., pi-acidic moieties); therefore the stronger pi-pi interaction which plays an important role in chiral recognition process is expected between aromatic analytes and this type of the CSP The enantiomeric separations of 11 piperazine derivatives as well as six racemates have been successfully achieved on this CSP in the normal and reversed phase modes. (c) 2008 Elsevier B.V. All rights reserved.