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.