Chromatographic resolution of enantiomers on a chiral stationary phase physically anchored to porous graphitic carbon

Abstract

A chrysene–tartramide derived chiral stationary phase (CSP) was prepared and adsorbed onto the surface of porous graphitic carbon (Hypercarb). The stereoselective properties of the carbon-based chiral stationary phase was evaluated in a pre-packed high-performance liquid chromatography column. The carbon-based CSP was found to be capable of separating the enantiomers of a range of compounds including 1,1′-bi(2-naphthol),2,2-diaminobinaphthalene, 1,5-hexadiene-3,4-diol, benzoin, 1,4-di-O-benzylthreitol, 1,1′-binaphthalene-2,2′-diylhydrogenphosphate, propranolol, nadolol and labetolol using a non-aqueous mobile phase. The addition of ammonium acetate to the mobile phase was found to improve the resolution of enantiomers for 1,1′-binaphthalene-2,2′-diylhydrogenphosphate, propranolol, nadolol and labetolol. The amount of chrysene–tartramide adsorbed on porous graphitic carbon was calculated from the cycling process and the value corresponded to 2.6% by mass of porous graphitic carbon.