Chiral covalent organic framework-monolith as stationary phase for high-performance liquid chromatographic enantioseparation of selected amino acids

The separation of amino acid (AA) enantiomers shows significance for chemistry, food, and biology, but remains challenging due to their similar properties. A promising nanoporous chiral covalent organic framework (COF) as a stationary phase for high-performance liquid chromatography (HPLC) suffers from the irregularity and widely distributed particle size of the chiral COF. Herein, we show the facile preparation of a chiral COF-monolith as a stationary phase for HPLC enantiomeric separation of AAs via orthogonal experiments. The CTzDa-monolith is prepared by the incorporation of the model chiral COF named CTzDa into the porous poly(ethylene dimethacrylate-co-methacrylate) monolith and reveals great permeability and mechanical stability. The corresponding CTzDa-monolithic column gives better chiral HPLC separation of AAs than the commercial Poroshell 120 chiral-T column. Thermal dynamic analysis and molecular docking calculations imply the involvement of stereoscopic hydrogen, pi-pi, and van der Waals interactions between the CTzDa and AAs during HPLC enantioseparation. The facile incorporation of the chiral COF into the porous monolith will promote the potential of a chiral COF as a stationary phase for HPLC.

Automated summary

The facile preparation of a chiral COF-monolith with high permeability and mechanical stability through orthogonal experiments was achieved for enantiomeric separation of AAs in HPLC. The resulting monolithic column showed better chiral HPLC separation performance than commercial columns, indicating the potential of chiral COF as a stationary phase for HPLC applications. Thermal dynamic analysis and molecular docking calculations suggested the involvement of stereoscopic interactions in the enantioseparation process.