Preparation and chromatographic properties of mixed-mode chromatographic stationary phases modified by imidazole side-group functionalized poly(ionic liquids)

doi:10.3724/SP.J.1123.2019.07029

Abstract

Abstract:

A novel mixed-mode chromatographic stationary phase was prepared via surface initiated atom transfer radical polymerization using an imidazole side-group functionalized ionic liquid monomer, 1-(4-vinylbenzyl)-3-cyanomethyl bromide. The structure of the stationary phase was characterized by infrared spectroscopy, elemental analysis, and thermogravimetric analysis. The stationary phase showed good separation ability. The retention mechanism of reversed-phase/ion exchange toward solutes on the stationary phase was verified by determining the effect of mobile phase pH on the retention of substances. Compared with octadecylsilyl-bonded silica stationary phase, it is confirmed that the poly(ionic liquid)-modified stationary phase provides π-π interaction toward the retention of the solutes. The results show that the functionalization of imidazole side groups is a feasible method for preparing new ionic liquid stationary phases.

Key words: atomic transfer radical polymerization (ATRP), poly(ionic liquids) (PILs), stationary phase, mixed-mode chromatography

CLC Number:

O658

WANG Jie, LIU Hong, WU Dan, ZHAO Bihong, SHEN Jiwei, WANG Chaozhan, WEI Yinmao. Preparation and chromatographic properties of mixed-mode chromatographic stationary phases modified by imidazole side-group functionalized poly(ionic liquids)[J]. Chinese Journal of Chromatography, 2020, 38(4): 424-429.

Figures/Tables 6

Fig. 1 Preparation route of stationary phase VBzIm: 1-(4-vinylbenzyl)-3-cyanomethylimidazole; ACN: acetonitrile; ILs: ionic liquids; SI-ATRP: surface-initiated atom transfer radical polymerization; PILs: poly(ionic liquids).

Fig. 2 (a) Infrared spectra and (b) thermogravimetric analysis of Silica-Cl and Silica-PILs

Fig. 3 Changes in (a) separation and (b) retention of polycyclic aromatic hydrocarbons for different acetonitrile contents in mobile phase Mobile phase: acetonitrile-water (25∶75, v/v). Peak Nos.: 1. naphthalene; 2. acenaphthene; 3. fluorene; 4. phenanthrene; 5. pyrene.

Fig. 4 Effects of pH on retention of (a) organic bases and (b) organic acids Mobile phase: acetonitrile-10 mmol/L ammonium formate (15∶85, v/v).

Fig. 5 Relationship between lg k and lg P of solutes on (a) Silica-PILs and (b) octadecylsilyl-bonded silica (ODS) stationary phases Mobile phase for Silica-PILs: CH3CN-H2O (25∶75, v/v); mobile phase for ODS: CH3CN-H2O (50∶50, v/v). Solutes: 1. toluene; 2. ethylbenzene; 3. propylbenzene; 4. butylbenzene; 5. pentylbenzene; 6. benzene; 7. naphthalene; 8. anthracene; 9. pyrene.

Fig. 6 Chromatographic separation of five non- steroidal anti-inflammatory drugs Mobile phase: acetonitrile-10 mmol/L ammonium formate (15∶85, v/v). Peak Nos.: 1. nimesulide; 2. ketoprofen; 3. fenbufen; 4. indomethacin; 5. diclofenac.

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