HPLC Retention Behaviors of Poly-aromatic-hydrocarbones on Cu(II)-octabromotetrakis(4-carboxyphenyl)porphine Derivatives-Immobilized Aminopropyl Silica Gels in Polar and Non-Polar Eluents

Abstract

As one of approaches of developing novel HPLC stationary phases, we prepared Cu-octabromotetrakis(4-carboxyphenyl)porphine derivative-immobilized silica gels (Cu-OBTCPP_D), and evaluated the availability of the resultant Cu-OBTCPP_D as a stationary phase for separation of poly-aromatic-hydrocarbons (PAHs) and their related compounds. A Cu-OBTCPP_D column was revealed to have an ability to separate simple PAHs and be useful as a stationary phase in both polar and non-polar eluents. The retention property of the Cu-OBTCPP_D column was evaluated in various comparative experiments using commercially available columns. In comparison with 2-(1-pyrenyl)ethyl dimetylsilyl silica gel column (PYE column) regarding the retention behavior for PAHs etc., the Cu-OBTCPP_D column showed stronger interactions involving π electron in non-polar eluent than PYE column. In comparison with a pentabromobenzyloxy propylsilyl silica gel column (PBB column) regarding the influence of bromination, the Cu-OBTCPP_D column was affected differently from the PBB column. In comparison with nitrophenylethyl silica gel column (NPE column) regarding the retention behavior for compounds having a dipole in a non-polar eluent, the Cu-OBTCPP_D column showed electrostatic interactions such as dipole–dipole interaction equivalent to or larger than the NPE column.