Chiral covalent organic framework incorporated organic polymer monolithic capillary column for enantioseparations

Abstract

A chiral covalent organic framework was synthesized, characterized, and incorporated into organic polymer monolithic capillary columns to provide chiral stationary phases for enantioseparations. The prepared monolithic capillary columns were characterized by scanning electron microscopy and elemental analysis. To obtain better enantioseparations, the columns’ preparation conditions, and enantioseparation conditions were optimized. Baseline resolutions of several chiral compounds were obtained with good reproducibility and stability. Furthermore, the mechanism of chiral recognition was investigated using molecular docking with AutoDock. Docking results showed that the enantioselectivity factor rather than resolution is correlated with the binding free energy difference between enantiomers with the chiral covalent organic framework. And abundant acetoxy and nitrile groups as well as benzene rings in the chiral covalent organic framework are responsible for the enantioseparation ability of the chiral monolithic capillary columns.

Study of the Enantioselectivity and Recognition Mechanism of Allyl‐β‐CD Modified Organic Polymer Monolithic Capillary Column

“…As shown in Figure 2C,D, a homogeneous and intact monolithic matrix with dense pores was observed, and the monolithic matrix is securely affixed to the inner wall of the capillary, indicating the successful preparation of CDOPMCC. Compared with other GMA‐EDMA monoliths [40], the surface morphology did not show significant differences. Furthermore, the specific surface area of CDOPMCC with 25‐mg allyl‐β‐CD was determined to be 7.48 m 2 /g according to the Brunauer–Emmett–Teller (BET) method.…”

A minireview on covalent organic frameworks as stationary phases in chromatography

“…COFs have also been incorporated into porous polymer monolithic columns to reduce column back-pressure ( Svec and Lv, 2015 ; Song et al, 2023 ). This strategy was recently employed by Yan and co-workers, who prepared the 3D imine-linked 3D-IL-COF-1 via solvothermal process instead of the previously reported ionothermal synthesis ( Guan et al, 2018 ).…”

Polypeptide-inspired supramolecular assemblies for enantioselective sorption of chiral molecules

“…17,18 Therefore, great efforts have been devoted to developing novel chiral materials for reproducing the functions of natural biomolecules in the last few decades. [19][20][21][22][23][24][25] As an intriguing class of crystalline materials, chiral coordination polymers composed of organic linkers and metal nodes have drawn significant attention because of their inherent porosity, well-defined structures, and chemical tunability, exhibiting promising applications in enantioselective processes. [26][27][28][29][30][31][32][33][34][35] For example, Cui's group has developed a lamellar homochiral supramolecular structure with a 1D flexible helical chain based on tridentate Schiff base metal complexes, exhibiting a high enantioselectivity in capturing chiral secondary alcohols.…”