Chiral Ionic Liquids in Chromatographic Separation and Spectroscopic Discrimination

Li, Min; Bwambok, David K.; Fakayode, Sayo O.; Warner, Isiah M.

doi:10.1007/978-3-642-12445-7_11

Cited by 8 publications

(6 citation statements)

References 126 publications

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Section: Classification and Application Of Ilsmentioning

confidence: 99%

“…To date, only a few reviews on the synthesis and utility of chiral ionic liquids have been published. Some of them focus their attention on the synthesis of CILs [22,23], the role of CILs in chiral recognition of the enantiomers using various analytical techniques such as NMR and spectroscopy [24,25], liquid and gas chromatography [24][25][26] and capillary electrophoresis [24,26]. This review collectively describes the advantages of using CILs for enantioseparation in tandem with extraction including aqueous biphasic system (ABS) extraction systems, solid-liquid two-phase systems, liquid-liquid extraction systems with hydrophilic CILs, liquid-liquid extraction systems with hydrophobic CILs, solid-phase extraction and induced-precipitation techniques and separation techniques such as liquid chromatography and countercurrent chromatography.…”

Section: Introductionmentioning

confidence: 99%

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Chiral Ionic Liquids: Structural Diversity, Properties and Applications in Selected Separation Techniques

Flieger

Feder‐Kubis

Tatarczak-Michalewska

2020

IJMS

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Ionic liquids (ILs) are chemical compounds composed of ions with melting points below 100 °C exhibiting a design feature. ILs are commonly used as the so-called green solvents, reagents or highly efficient catalysts in varied chemical processes. The huge application potential of ionic liquids (IL) justifies the growing interest in these compounds. In the last decade, increasing attention has been devoted to the development of new methods in the synthesis of stable chiral ionic liquids (CILs) and their application in various separation techniques. The beginnings of the successful use of CILs to separate enantiomers date back to the 1990 s. Most chiral ILs are based on chiral cations or chiral anions. There is also a limited number of CILs possessing both a chiral cation and a chiral anion. Due to the high molecular diversity of both ions, of which at least one has a chiral center, we have the possibility to design a large variety of optically active structures, thus expanding the range of CIL applications. Research utilizing chiral ionic liquids only recently has become more popular. However, it is the area that still has great potential for future development. This review aimed to describe the diversity of structures, properties and examples of applications of chiral ionic liquids as new chiral solid materials and chiral components of the anisotropic environment, providing chiral recognition of enantiomeric analytes, which is useful in liquid chromatography, countercurrent chromatography and other various CIL-based extraction techniques including aqueous biphasic (ABS) extraction systems, solid–liquid two-phase systems, liquid–liquid extraction systems with hydrophilic CILs, liquid–liquid extraction systems with hydrophobic CILs, solid-phase extraction and induced-precipitation techniques developed in the recent years. The growing demand for pure enantiomers in the pharmaceutical and food industries sparks further development in the field of extraction and separation systems modified with CILs highlighting them as affordable and environmentally friendly both chiral selectors and solvents.

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Section: Classification and Application Of Ilsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Chiral Ionic Liquids: Structural Diversity, Properties and Applications in Selected Separation Techniques

Flieger

Feder‐Kubis

Tatarczak-Michalewska

2020

IJMS

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“…At present, there have been various chiral selectors that can be used for enantiomeric separation, such as cyclodextrins, polysaccharides, macrocyclic antibiotics, proteins, crown ethers, etc. However, the use of these chiral selectors is often limited due to their low solubility, difficult syntheses, and instability at high temperature as well as high cost . Recently, the most attractive interest is the development of novel selectors with reduced toxicity, environmentally benign capability, good biodegradability, and high biocompatibility .…”

Section: Introductionmentioning

confidence: 99%

“…However, the use of these chiral selectors is often limited due to their low solubility, difficult syntheses, and instability at high temperature as well as high cost. 20 Recently, the most attractive interest is the development of novel selectors with reduced toxicity, environmentally benign capability, good biodegradability, and high biocompatibility. 21 In this regard, much attention has been devoted to chiral ionic liquids (CILs) derived from natural sources.…”

Section: Introductionmentioning

confidence: 99%

Separation of Tryptophan Enantiomers by Ligand‐Exchange Chromatography With Novel Chiral Ionic Liquids Ligand

Qing

Jiang

2014

Chirality

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Chiral ionic liquids (CILs) with amino acids as cations have been applied as novel chiral ligands coordinated with Cu(2+) to separate tryptophan enantiomers in ligand exchange chromatography. Four kinds of amino acid ionic liquids, including [L-Pro][CF3COO], [L-Pro][NO3], [L-Pro]2[SO4], and [L-Phe][CF3COO] were successfully synthesized and used for separation of tryptophan enantiomers. To optimize the separation conditions, [L-Pro][CF3COO] was selected as the model ligand. Some factors influencing the efficiency of chiral separation, such as copper ion concentration, CILs concentration, methanol ratio (methanol/H2O, v/v), and pH, were investigated. The obtained optimal separation conditions were as follows: 8.0 mmol/L Cu(OAc)2, 4.0 mmol/L [L-Pro][CF3COO], and 20% (v/v) methanol at pH 3.6. Under the optimum conditions, acceptable enantioseparation of tryptophan enantiomers could be observed with a resolution of 1.89. The results demonstrate the good applicability of CILs with amino acids as cations for chiral separation. Furthermore, a comparative study was also conducted for exploring the mechanism of the CILs as new ligands in ligand exchange chromatography.

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“…Amino acids from the chiral pool seemed to be ideal precursors for this purpose due to their good availability and their low price. Most examples, which use amino acids as precursors or reagents, are from task‐specific ILs,2e,g,h, 4 where the amino acid can be either the cation2g,j or the anion 2d,f. 5 In the case of ILs with amino acid anions 1‐ethyl‐3‐methylimidazolium hydroxide was neutralised with the neat amino acid2d, 5 to yield compounds 1 (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Ionic Liquid Crystals Derived from Amino Acids

Mansueto

Frey

Laschat

2013

Chemistry A European J

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Novel chiral amino acid derived ionic liquid crystals with amine and amide moieties as spacers between the imidazolium head group and the alkyl chain were synthesised. The key step in the synthesis utilised the relatively uncommon SO3 leaving group in a microwave-assisted reaction. The mesomorphic properties of the mesogens were determined by differential scanning calorimetry (DSC), polarising optical microscopy (POM) and X-ray diffraction. All liquid crystalline salts exhibit a smectic A mesophase geometry with strongly interdigitated bilayer structures. An increase of the steric bulk of the stereogenic centre hindered the formation of mesophases. In case of phenylalanine-derived derivatives a mesomorphic behaviour was observed for shorter alkyl chains as compared to other amino acid derivatives indicating an additional stabilising effect by the phenyl moiety.

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Chiral Ionic Liquids in Chromatographic Separation and Spectroscopic Discrimination

Cited by 8 publications

References 126 publications

Chiral Ionic Liquids: Structural Diversity, Properties and Applications in Selected Separation Techniques

Chiral Ionic Liquids: Structural Diversity, Properties and Applications in Selected Separation Techniques

Separation of Tryptophan Enantiomers by Ligand‐Exchange Chromatography With Novel Chiral Ionic Liquids Ligand

Ionic Liquid Crystals Derived from Amino Acids

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