Cyclodextrin‐NH‐MIL‐53 open tubular stationary phase for capillary electrochromatography enantioseparation

Abstract

A novel chiral group functionalized metal-organic framework, Cyclodextrin-NH-MIL-53, was synthesized and modified on the inner wall of a capillary column via a post-synthetic process. The prepared chiral metal-organic framework was utilized as a chiral capillary stationary phase and used in an open-tubular capillary electrochromatography method to enantioseparate several racemic amino acids. Excellent enantioseparation of five pairs of enantiomers was obtained in this chiral separation system (Resolutions of D/L-Alanine = 16.844, D/L-Cysteine = 3.617, D/L-Histidine = 9.513, D/L-Phenylalanine = 8.133, and D/L-Tryptophan = 2.778). The prepared Cyclodextrin-NH-MIL-53 and the Cyclodextrin-NH-MIL-53-based capillary columns were characterized by scanning electron microscopy, X-ray diffraction, Fourie-transform infrared spectroscopy, and circular dichroism. The chiral capillary electrochromatography conditions, such as separation conditions, amount of Cyclodextrin-NH-MIL-53, and electroosmotic flow, were optimized. This research is estimated to present a novel insight and method for the design and use of metal-organic framework-based capillaries for enantioseparation.

Enantioseparation of agrochemicals by gas chromatography. Exploring columns based on cyclodextrin derivatives dissolved into polysiloxanes

“…Enantiomeric analysis can be performed by different analytical techniques [5][6][7][8][9][10][11]. A comprehensive compilation and classification of chiral agrochemicals according to their primarily used, [12], gathered information on enantioseparation methods for those agrochemicals by liquid chromatography (LC), gas chromatography (GC), and capillary electrophoresis (CE).…”

Synthesis Strategies, Preparation Methods, and Applications of Chiral Metal‐Organic Frameworks

“…CMOFs have a chiral structure and are used differently from metal-organic frameworks. CMOFs have novel applications in enantiomer recognition, [12,13] enantiomer separation, [14,15] circularly polarized luminescence, [16,17] and heterogeneous asymmetric catalysis. [18,19] In 2000, Kim and his colleagues directly synthesized CMOFs (D or L-Post-1) with pure enantiomeric ligands and successfully applied them to asymmetric catalysis.…”

High-Enantioselectivity Adsorption Separation of Racemic Mandelic Acid and Methyl Mandelate by Robust Chiral UiO-68-Type Zr-MOFs

“…Chirality is a fundamental characteristic of nature and plays an integral role in many fields, such as biological molecules, pharmaceuticals, food additives, etc. − Chiral compounds usually contain two or more enantiomers. Efficient enantioselective separation of chiral molecules, especially chiral drugs, is of pivotal significance since different enantiomer exhibits different pharmacological, biological, and toxicological activities in living systems, which has also led to an increasing demand for enantiomerically pure compounds and advanced materials. − To date, several chiral separation methods have proven to be effective in enantiomeric separation and have even been developed in industrial processes, such as crystallization purification, − chromatographic separation, − membrane separation, − etc. However, they often suffer from operational complexity, high price, low efficiency, and instability.…”