Preparation and application of quinine-functionalized poly(1-vinylimidazole)-modified silica stationary phase in hydrophilic interaction chromatography

doi:10.3724/SP.J.1123.2019.06008

Abstract

Abstract:

A quinine-functionalized poly(1-vinylimidazole)-modified hydrophilic silica stationary phase (Sil-PIm-Qn) was prepared by surface radical chain transfer and nucleophilic substitution reactions. Sil-PIm-Qn was characterized by elemental analysis and FT-IR. The chromatographic characteristics of the stationary phase were investigated in the hydrophilic interaction chromatographic (HILIC) mode. The results showed that five amino acids, nine sulfonamides, and ten nucleosides/nucleobases could be successfully separated on this stationary phase, respectively. The retention behavior of the compounds on the column was evaluated under different chromatographic conditions, i. e., for different salt concentrations and acetonitrile contents in the mobile phases. The stability of this column was also investigated, and the relative standard deviation (RSD, n=10) of the retention time of Sil-PIm-Qn was 0.08%-2.30%. Given its simple and green preparation as well as its unique selectivity and high separation efficiency, Sil-PIm-Qn is expected to find widespread application in the separation of hydrophilic compounds, including sulfonamides and nucleosides/nucleobases, in real samples.

Key words: hydrophilic interaction chromatography (HILIC), chromatographic stationary phase, preparation, quinine, poly(1-vinylimidazole), hydrophilic compounds

CLC Number:

O658

ZHOU Hang, CHEN Jia, ZHANG Yingshan, ZHAO Liang, QIU Hongdeng. Preparation and application of quinine-functionalized poly(1-vinylimidazole)-modified silica stationary phase in hydrophilic interaction chromatography[J]. Chinese Journal of Chromatography, 2020, 38(4): 438-444.

Figures/Tables 9

Fig. 1 Schematic diagram for the preparation of Sil-PIm-Qn Sil-PIm-Qn: quinine-functionalized poly(1-vinylimidazole)-modified hydrophilic silica stationary phase; Sil-MPS: γ-mercaptopropyltriethoxysilane-modified silica; DES: deep eutectic solvents.

Table 1 Elemental analysis results of bare silica, Sil-MPS, Sil-PIm and Sil-PIm-Qn

Analyte	Elemental contents/%
Analyte	N	C	H
Bare silica	0	0.94	0.44
Sil-MPS	0	4.01	0.71
Sil-PIm	2.62	8.70	1.09
Sil-PIm-Qn	3.20	11.18	1.44

Fig. 2 FT-IR spectra of the Sil-MPS, Sil-PIm and Sil-PIm-Qn

Fig. 3 1H NMR of 2-chloroethyl isocyanate-modified quinine (Ci-Qn)

Fig. 4 Chromatogram of the five amino acids on the Sil-PIm-Qn column

Fig. 5 Chromatograms of the nine sulfonamides on the (a) Sil-PIm-Qn and (b) Sil-PIm columns

Fig. 6 Chromatogram of the ten nucleosides and nucleobases on the Sil-PIm-Qn column

Fig. 7 Plots of lg k vs. volume fractions of acetonitrile in the mobile phase for the eight nucleosides and nucleobases on the Sil-PIm-Qn column k: retention factor.

Fig. 8 Plots of lg k vs. concentrations of ammonium acetate in the mobile phases for the eight nucleosides and nucleobases on the Sil-PIm-Qn column

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