DEVELOPMENT OF CHIRAL STATIONARY PHASES FOR THE ENANTIOMERIC RESOLUTION OF DIHYDRODIOLS OF POLYCYCLIC AROMATIC-HYDROCARBONS BY PI-DONOR-ACCEPTOR INTERACTIONS

Chiral stationary phases (CSPs) derived from (R)-(-)-2-(2,4,5,7-tetranitrofluoren-9-ylideneaminooxy)propionic acid (TAPA) covalently bound to silica gel have been developed by altering the alkyl group at the chiral centre or the number of aromatic rings and their degree of nitration. The chromatographic properties of the CSPs were characterized by use of a racemic model solute. Depending on the solvent strength of the mobile phase, the CSPs exhibit the quality of a normal or a reversed phase. The chromatographic behaviour of 30 racemic hydroxylated derivatives of polycyclic aromatic hydrocarbons (PAHs) on (R)-(-)TAPA CSP revealed the structural requirements for chiral recognition. The applicability of the CSPs for the enantiomeric separation of trans-dihydrodiols of PAHs on an analytical as well as preparative scale and for investigating the enantioselectivity of the biotransformation and genotoxicity of PAHs is demonstrated.