Synthesis of β-Cyclodextrin–Calix[4]arene Polymer-Based Chiral Stationary Phase for Chromatographic Separation of Enantiomers

In this work, a new strategy was proposed for the preparation of a chiral stationary phase based on β-cyclodextrin and calix[4]arene polymer. The chiral stationary phase was characterized by scanning electron microscopy, energy dispersive x-ray spectroscopy, Fourier transform infrared spectroscopy, and thermogravimetric analysis. The introduction of calix[4]arene polymer increased chirality recognition by increasing recognition sites and interactions, including hydrogen bonding, π–π interaction and synergistic inclusion effect. Compared with the home-made β-cyclodextrin–based chiral column, the prepared β-cyclodextrin–calix[4]arene polymer-based chiral column showed superior enantioseparation performance toward 1-phenylethanol, prothioconazole, promethazine, propranolol, and bisoprolol. These chiral compounds can be separated within 10 min under reversed-phase mode with resolutions ranging from 1.62 to 1.80. These findings will provide an important reference for developing novel supramolecule-based chiral stationary phases.