Preparation and enantioseparation property of chiral stationary phases based on cellulose tris(3,5-dimethylbenzoate) — A new way to prepare polysaccharide-coating type chiral stationary phases

Abstract

A new method to prepare polysaccharide-coating type chiral stationary phases (CSPs) was developed in this work. As a typical example, naked silica gel was coated by cellulose, which was then derivatized with 3,5-dimethylbenzoyl chloride to afford cellulose tris(3,5-dimethylbenzoate)-silica gel (CTDBS) complex. The silanols on CTDBS were end-capped with 3-aminopropyltriethoxysilane to obtain CSP 1. The amino groups on CSP 1 were further end-capped with 3,5-dimethylbenzoyl chloride to give CSP 2. The silanols on CTDBS were end-capped with methyltrimethoxysilane to yield CSP 3. CSPs 1–3 were characterized by FTIR, solid-state 13C-NMR and elemental analysis. The enantioseparation abilities of CSPs 1–3 were evaluated with structurally various chiral analytes. The enantioseparation results demonstrated that the end-capping moieties on CSPs 1 and 2 significantly affected enantioseparation. In addition, the effect of the structures of chiral analytes and endcapping moieties on the retention factors and the resolutions was discussed.