Application of a Chiral Stationary Phase Based on 3,4,9,10-Perylenetetracarboxylic Acid to the Separation of Enantiomers under the Conditions of Gas and Liquid Chromatography

Abstract

A chiral stationary phase is proposed on the basis of 3,4,9,10-perylenetetracarboxylic acid (3,4,9,10-perylentetracarbonacid, PTCA). The PTCA molecule itself is not chiral; however, it can form chiral supramolecular structures. Symmetry breaking during the self-assembly of PTCA supramolecular structures was carried out similarly to the Viedma ripening process. The obtained stationary phases with PTCA multilayers on an inert solid support and C18 silica were used to separate racemates in gas and liquid chromatography, respectively. It was found that the proposed stationary phases exhibit enantioselectivity with respect to pairs of enantiomers bearing a hydroxyl group at an asymmetric carbon atom. Enantiomers of butanol-2, pentanol-2, and 1-methoxy-propanol-2 were separated by gas chromatography. The separation of menthols was achieved in the normal-phase HPLC mode. It was shown that the separation of the last named compounds is possible up to a concentration of 0.04 mg/mL inclusive.