Synthesis and application of a chiral ionic liquid functionalized <i>β</i>‐cyclodextrin as a chiral selector in capillary electrophoresis

Yu, Jia; Zuo, Li; Liu, Hongjiao; Zhang, Lijuan; Guo, Xingjie

doi:10.1002/bmc.2900

Cited by 36 publications

(21 citation statements)

References 32 publications

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“…The use of ionic-liquid-functionalized β-CD [(HPTMA-β-CD)(BF 4 )] was reported for CE enantioseparations of chlorpheniramine, brompheniramine, promethazine, liarozole, tropicamide, warfarin, pheniramine and bifonazole enantiomers [32]. (HPTMA-β-CD)(BF 4 ) not only increased the water solubility but also afforded a stable reversed EOF.…”

Section: Monocationic and Dual-cationic Cds As Chiral Additivesmentioning

confidence: 99%

Recent development of cationic cyclodextrins for chiral separation

Zhou

Tang

2015

TrAC Trends in Analytical Chemistry

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Section: Monocationic and Dual-cationic Cds As Chiral Additivesmentioning

confidence: 99%

Recent development of cationic cyclodextrins for chiral separation

Zhou

Tang

2015

TrAC Trends in Analytical Chemistry

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“…Anionic β ‐CD derivatives bearing sulfonates and carboxylates have been extensively investigated as chiral selectors (Chen et al ., ; Mandrioli et al ., ; Kirschner et al ., ; Jiang et al ., ). Cationic β ‐CD derivatives are typically β ‐CD derivatized with nitrogen‐containing functionalities that can carry positive charges, but these are relatively less frequently used in chiral separation (Lin et al ., ; Xiao et al ., ; Yu et al ., ). This might be because properly substituted cationic β ‐CD derivatives are not always commercially available and are somewhat more challenging to synthesize.…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation of meptazinol and its three intermediate enantiomers by capillary electrophoresis using a new cationicβ‐cyclodextrin derivative in single and dual cyclodextrin systems

Zhao

Song

et al. 2014

Biomedical Chromatography

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A new cationic β-cyclodextrin derivative, mono-6-deoxy-6-piperdine-β-cyclodextrin (PIP-β-CD), was synthesized and applied as a chiral selector for the enantioseparation of meptazinol and its three intermediate enantiomers (intermediates II-IV) in capillary electrophoresis. When PIP-β-CD was employed as the single CD system, intermediate II was baseline enantioseparated while the results for the other analytes were less satisfactory. In order to enhance the selectivity and resolution of meptazinol intermediate III and intermediate IV, dual CD systems of PIP-β-CD in combination with three different neutral CDs were synthesized and tested: β-cyclodextrin (β-CD), trimethyl-β-cyclodextrin (TM-β-CD) and hydroxypropyl-β-cyclodextrin (HP-β-CD). After investigating the effect on the enantioseparation efficiency of the nature and the concentration of both CDs, the dual CD system consisting of PIP-β-CD and HP-β-CD was shown to be the most efficient for the simultaneous enantioseparation of meptazinol intermediates III and IV.

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“…The aforementioned unique properties allow ionic liquids to be widely applied in various analytical applications including gas chromatography [2][3][4], high-performance liquid chromatography [5], solvent-based microextraction [6], sorption-based extractions [7,8], capillary electrophoresis [9,10], mass spectrometry [11], and electrochemical sensing systems [12].…”

Section: Introductionmentioning

confidence: 99%

Capillary column coated with geminal ionic liquids as stationary phases for gas chromatographic separation

Jiang¹,

Liu²,

Yang³

et al. 2017

Acta Chromatographica

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Summary. Four geminal ionic liquids (GILs), namely, 1,4-bis(1,1′-butyl-3,3′-methylene-imidazolium)-benzene bis[(trifluoromethyl)sulfonyl]imide (BBMIB-NTf2), 1,4-bis(1,1′-butyl-3,3′-methylene-imidazolium)-benzene tetrafluoroborate (BBMIB-BF4), 1,4-bis(1,1′-butyl-3,3′-methylene-imidazolium)-benzene hexafluophosphate (BBMIB-PF6), and 1,4-bis(1,1′-methyl-3,3′-methylene-imidazolium)-benzene bis[(trifluoromethyl) sulfonyl]imide (BMMIB-NTf2), were synthesized. They were statically coated onto the inner walls of fused-silica capillary columns and used as stationary phases for gas chromatography. The evaluation of BBMIB-NTf2, BBMIB-BF4, BBMIB-PF6, and BMMIB-NTf2 as stationary phases is reported here for the first time. These new stationary phases exhibit efficiencies of at least 2.3 × 10 3 plates per meter. Abraham solvation parameter model was used to evaluate the solvation characteristics. The system constants indicated that the dipolarity/polarizability and the hydrogen-bond basicity play a major role among five molecular interactions between stationary phases and solute molecules. A fundamental understanding into the solvation characteristics of these GILs can be used as a guide to choosing the appropriate geminal ionic liquids for specific applications in various fields. The chromatographic separation performance was evaluated by a Grob test mixture, n-alkanes, alcohols, and aromatic isomers. Furthermore, the thermal stability was tested. The present results demonstrate that these geminal ionic liquids stationary phases possess excellent chromatographic separation performance and good thermal stability (at least up to 270 °C) and may be applicable as gas chromatography stationary phases for more application.

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Synthesis and application of a chiral ionic liquid functionalized β‐cyclodextrin as a chiral selector in capillary electrophoresis

Cited by 36 publications

References 32 publications

Recent development of cationic cyclodextrins for chiral separation

Recent development of cationic cyclodextrins for chiral separation

Enantioseparation of meptazinol and its three intermediate enantiomers by capillary electrophoresis using a new cationicβ‐cyclodextrin derivative in single and dual cyclodextrin systems

Capillary column coated with geminal ionic liquids as stationary phases for gas chromatographic separation

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