Construction of β-Cyclodextrin Covalent Organic Framework-Modified Chiral Stationary Phase for Chiral Separation

Chiral covalent organic frameworks (CCOFs), built by the condensation reactions of organic building blocks with enantiomeric purity and linking subunits, have emerged as a marvelous category of porous crystalline material. In addition to stability and good porosity, CCOFs possess remarkable enantioselectivity, which would be exploited for asymmetric catalysis and chiral separation. β-cyclodextrin (β-CD) and its derivatives, a group of supramolecules with a hydrophobic cavity, have been widely applied to molecular specific recognitions. In this work, the β-CD covalent organic framework (COF) was exploited to construct chiral stationary phase (CSP) for chiral drugs analysis for the first time. We fabricated β-CD COF via the condensation reaction of heptakis(6-amino-6-deoxy)-β-CD and terephthalaldehyde at room temperature. β-CD COF-modified capillary columns were subsequently prepared by a photopolymerization method with shortened time and applied for separation of chiral drugs on capillary electrochromatography with good resolution and repeatability. Baseline separation for six enantiomers was achieved and the precisions (relative standard deviations) for intraday, interday, and column-to-column were <2.1%, 4.5%, and 7.3%, respectively. The results reveal that CCOFs-coated capillary columns show great prospect for chromatographic separation of chiral drugs.