Preparation and evaluation of biselector bonded‐type multifunctional chiral stationary phase based on dialdehyde cellulose and 6‐monodeoxy‐6‐monoamino‐β‐cyclodextrine derivatives

Abstract

A novel biselector bonded‐type multifunctional chiral stationary phase (MCSP) was prepared by covalently crosslinking dialdehyde cellulose (DAC) with 6‐monodeoxy‐6‐monoamino‐β‐cyclodextrine (CD) via Schiff base reaction. The biselector bonded‐type MCSP had good chiral and achiral chromatographic performance in normal phase (NP) and reversed phase (RP) modes. Seven and eight enantiomers were successfully separated on the prepared biselector bonded‐type MCSP in NP and RP modes, respectively. The biselector bonded‐type MCSP showed enhanced chiral resolution ability compared with single selector chiral stationary phases due to the simultaneous introduction of DAC and 6‐monodeoxy‐6‐monoamino‐β‐CD on the surface of silica gel. Aromatic compounds including polycyclic aromatic hydrocarbons, anilines, phenols, phenylates, and aromatic acids were choosed as analytes to investigate the achiral chromatographic performance of the biselector bonded‐type MCSP in NP and RP modes. Chromatographic evaluation results showed that the above aromatic compounds were essentially capable of achieving baseline separation by hydrophobic interaction, π‐π interaction, and π‐π electron‐donor‐acceptor interaction. Moreover, the host‐guest inclusion effect of 6‐monodeoxy‐6‐monoamino‐β‐CD and the multiple interactions made the biselector bonded‐type MCSP have good steric selectivity. The preparation method of the biselector bonded‐type MCSP was simple and provided a new idea and strategy for the preparation of the subsequent novel biselector MCSP.

Recent progress in the development of chiral stationary phases for high‐performance liquid chromatography

“…New derivatives of cellulose and amylose are mainly prepared by derivatizing hydroxyl groups at the C-2, C-3, and C-6 positions with different substituted phenyl groups [112][113][114]. Other novel derivatives of cellulose have also been reported, such as modified dialdehyde cellulose derivatives [115,116], cellulose dodecanoate [117], cellulose 6-acetamido-6-deoxy-2,3-bis(phenylcarbamate)s [118] and cellulose and CD derivatives biselectors [119,120].…”

Polysaccharide- and β-Cyclodextrin-Based Chiral Selectors for Enantiomer Resolution: Recent Developments and Applications

“…Anchoring another polymeric CS onto the cellulose backbone, to enhance chiral recognition ability, was investigated by Qian et al and Gao et al [ 20 , 21 ]. A new generation of cellulose-grafted copolymers as CS has been discovered by Qian et al [ 20 ].…”

“…The chirality of cellulose and β-cyclodextrin may be complementary or synergistic, thus a combination of those two types of materials to enhance the overall ES performance was investigated by Gao et al [ 21 ]. Dialdehyde cellulose derivatives were prepared by a selective oxidation reaction of microcrystalline cellulose with sodium periodate, and then the materials were immobilized onto the surface of amino-modified silica gel by a Schiff’s base reaction and allowed to react with 6-monodeoxy-6-monoamino-β-cyclodextrin to generate silica-bound bis -selectors.…”