Synthesis and chromatographic evaluation of phenyl/tetrazole bonded stationary phase based on thiol‐epoxy ring opening reaction

Abstract

A silica-based reversed-phase stationary phase bonding with phenyl and tetrazole groups was synthesized by thiol-epoxy ring opening reaction. The bonded groups could not only provide hydrophobic interaction, but also π-π, hydrogen bonding, electrostatic interactions, and so on. The results of characterization with elemental analysis and solid-state C cross-polarization magic-angle-spinning NMR spectroscopy indicated the successful preparation of phenyl/tetrazole sulfoether bonded stationary phase. Chromatographic evaluation revealed that phenyl/tetrazole sulfoether bonded stationary phase behaved well under the reversed-phase mode. The column parameters (H, S*, A, B, and C) showed different selectivity compared with some typical commercial columns, and it was validated by the separation of estrogen, ginsenoside, alkaloid samples. Based on the different selectivity between phenyl/tetrazole sulfoether bonded stationary phase and C18 columns, phenyl/tetrazole sulfoether bonded stationary phase also showed potential to construct a 2D reversed-phase liquid chromatography system with C18. And it was verified by the separation of corydalis tuber and curcuma zedoary extracts.

Preparative isolation of 1,1‐diphenyl‐2‐picrylhydrazyl inhibitors from Ribes himalense using medium‐pressure and two‐dimensional reversed‐phase/reversed‐phase liquid chromatography guided by an online HPLC‐1, 1‐diphenyl‐2‐picrylhydrazyl assay

“…Relative to other 2D combinations, an RPLC/RPLC 2D approach is better suited to separating nonpolar, polar and ionic compounds [29, 30]. The PTAS column filler exhibited typical RPLC retention characteristics, which showed good separation selectivity for hydrophobic compounds [31]. However, the mechanism of synthesis of PTAS is different from that of common C18 reversed‐phase column fillers, it has the potential to constitute a 2D RPLC/RPLC combination with a C18 RP column.…”

Synthesis and evaluation of a pentafluorobenzamide stationary phase for HPLC separations in the reversed phase and hydrophilic interaction modes

“…The introduction of phenyl groups into the structure of chromatographic packings offers additional interactions, especially π‐π interactions, which are interesting for the separation of aromatic compounds, due to improved selectivity . Phenyl phases with embedded polar groups were explored for the separation of aromatic compounds, and it was concluded that the presence of polar functional groups incorporated into the structure of bonded ligands changes the solvation process due to polar interactions and hydrogen bond formation .…”