Quinine Derivative Bonded the Hybrid Mesoporous Silicas Chiral Stationary Phase: Preparation and Application in Liquid Chromatography

A novel chiral stationary phase (QN-APEPMOs) was synthesized by immobilizing quinine derivative (QN) onto spherical ammoniapropyl-functionalized ethane-bridged periodic mesoporous organosilicas (APEPMOs). The mesoporous material was prepared by a one-step co-condensation of 1,2-bis (triethoxysilyl) ethane (BTSE) and 3-ammoniapropyl triethoxysilane (KH-550) using cetyltrimethyl-ammoniumchlorine (C₁₈TACl) as a template with the aid of ethanol (co-solvent) in basic medium. And O-9-(tert-butyl carbamoyl) quinine derivative was immobilized on APEPMOs particles through the vinylic double bond. All of the products were characterized. The results showed that APEPMOs were perfect substrates for chiral stationary phase (CSP) and quinine moieties have been successfully immobilized onto the silica gel. To evaluate the chiral discrimination ability of the synthesized CSP, some analytes have been investigated on QN-APEPMOs in high performance liquid chromatography (RP-HPLC) in reversed phase. Three acidic compounds were baseline separated. The results demonstrated that QN-APEPMOs had high selectivity for acidic compounds such as: carboxylic and sulfonic acids. And the reproducibility of the chiral column was good, while the stability was not very good.