Synthesis and enantioseparation characteristics of a novel β-cyclodextrin chiral stationary phase based on diazotized silica in HPLC

Abstract

A novel chiral selector polyacrylic acid-β-cyclodextrin (PAA-β-CD) was successfully prepared, then a facile synthesis of PAA-β-CD stationary phase based on diazotized silica was developed and characterized. Monodisperse silica microspheres were synthesized by a modified Stöber method. The obtained silica particles were functionalized by self-assembly positive charged photosensitive diazoresin (DR) and PAA-β-CD on the surface. The corresponding chiral stationary phase (CSP) was used in HPLC and the enantioseparation performance was investigated in both polar organic and reverse phase mode. Better separation abilities and excellent enantio-selectivities were obtained on PAA-β-CD CSP for antihistamine drugs in the acetonitrile and triethylammonium acetate buffer mobile phase.

Abbreviations: AIBN: azodiisobutyronitrile; β-CD: b-cyclodextrin; β-CD-NH2: amino-β-CDcyclodextrin; β-CD-OTs: sulfonyl-b-cyclodextrin; CD: cyclodextrin; CSP: chiral stationary phase; DCC: dicyclohexyl carbimide; DR: diazoresin; MeOH: methanol; NMP: N-methyl pyrrolidone; PAA: polyacrylic acid; PAA-β-CD: polyacrylic acid-β-cyclodextrin; TEAA: triethylammonium acetate; TEOS: tetraethyl orthosilicate

Keywords:

• Diazoresin
• silica microspheres
• β-cyclodextrin
• liquid chromatography

Conflict of interest

The authors have declared no conflict of interest.

Additional information

Funding

This work was financially supported by the National Natural Science Foundation of China (21874078, 22074072), the Taishan Young Scholar Program of Shandong Province (tsqn20161027), the Major Science and Technology Innovation Project of Shandong Province (2018CXGC1407), the Key Research and Development Project of Shandong Province (2016GGX102028, 2016GGX102039, 2017GGX20111), and the First Class Discipline Project of Shandong Province.