Chiral protic imidazolium salts with a (−)-menthol fragment in the cation: synthesis, properties and use in the Diels–Alder reaction

Januś, Ewa; Gano, Marcin; Feder‐Kubis, Joanna; Sośnicki, Jacek G.

doi:10.1039/c7ra12176h

Cited by 13 publications

(13 citation statements)

References 41 publications

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“…13–23 in Figure 2 were synthesized by our team. CILs with menthoxymethyl substituent(s) ( Men ) and various ammonium groups: imidazolium [ 36 , 37 , 38 , 39 ], pyridinium [ 40 ], and alkylammonium [ 41 ] groups (nos. 13–21 in Figure 2 ) were synthesized according to procedures given in the references.…”

Section: Methodsmentioning

confidence: 99%

On the Miscibility of Nematic Liquid Crystals with Ionic Liquids and Joint Reaction for High Helical Twisting Power Product(s)

et al. 2021

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Mixtures of nematic liquid crystals (LCs) with chiral ionic liquids (CILs) may find application as active materials for electrically driven broadband mirrors. Five nematic liquid crystal hosts were mixed with twenty three ionic liquids, including chiral ones, and studied in terms of their miscibility within the nematic phase. Phase diagrams of the mixtures with CILs which exhibited twisted nematic phase were determined. Miscibility, at levels between 2 and 5 wt%, was found in six mixtures with cyanobiphenyl-based liquid crystal host—E7. On the other hand, the highest changes in the isotropization temperature was found in the mixtures with isothiocyanate-based liquid crystal host—1825. Occurrence of chemical reactions was found. A novel chiral binaphtyl-based organic salt [N11116][BNDP] was synthesized and, in reaction to the 1825 host, resulted in high helical twisting power product(s). Selectivity of the reaction with the isothiocyanate-based liquid crystal was found.

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Section: Methodsmentioning

confidence: 99%

On the Miscibility of Nematic Liquid Crystals with Ionic Liquids and Joint Reaction for High Helical Twisting Power Product(s)

et al. 2021

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“…chiral: (S)-2-hydroxypropionate derivative; (L-lactate) Diels-Alder reaction [7] (1R,2S,5R)-(-)-menthol derivative Diels-Alder reaction [33] L-(-)-malic acid derivative Aza-Baylis-Hillman reaction [61] chiral recognition in spectroscopy: 19 F NMR, fluorescence [70] chiral: (S)-2-hydroxypropionate derivative; (l-lactate) Diels-Alder reaction [7] Int. J. Mol.…”

Section: Structure Application Referencementioning

confidence: 99%

“…Sci. 2020, 21, x FOR PEER REVIEW 6 of 39 Diels-Alder reaction [7] (1R,2S,5R)-(-)-menthol derivative Diels-Alder reaction [33] L-(-)-malic acid derivative Aza-Baylis-Hillman reaction [61] chiral recognition in spectroscopy: 19 F NMR, fluorescence [70] (1R,2S,5R)-(-)-menthol derivative [68] Several chiral ionic liquids, which have been synthesized, have either a chiral cation, a chiral anion or both. An example of which is shown in a work written by Yu et al [79], describing the chiral recognition of newly synthesized CILs containing cations with an imidazolium group and anions based on a borate ion with spiral structure and chiral substituents.…”

Section: Structure Application Referencementioning

confidence: 99%

“…The obvious consequence of the rapidly expanding interest in ionic liquids is the growing number of applications in which these ionic salts are being used [ 10 , 29 , 30 , 31 ], for purposes as diverse as catalysis [ 32 , 33 ], fuel cells [ 34 ], safe electrolytes [ 35 , 36 ], lubrication [ 37 , 38 ], biomass treatment [ 39 ] and energy storage [ 17 , 40 , 41 ]. In the field of analytical chemistry, ILs have gained greatest popularity in various types of extractions, separations and identification techniques, i.e., gas chromatography (GC), liquid chromatography (LC), capillary electrophoresis (CE), electrochemistry or mass spectrometry (MS) [ 24 , 26 , 42 , 43 ].…”

Section: Classification and Application Of Ilsmentioning

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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“… 25 − 27 , 30 , 31 ILs with the (−)-menthol substituent have also been tested by our group for their catalytic activity (cycloisomerization and Diels–Alder reaction). 28 , 29 Another beneficial feature of these salts is their high antielectrostatic activity. 25 For such applications, the method of applying a substance that removes the electric charge from a polymer surface is crucial from a technical perspective and is directly related to the viscosity of the applied system.…”

Section: Introductionmentioning

confidence: 99%

On the Influence of the Menthol Moiety on the Transport Properties of a Homologue Series of Functionalized Bis(trifluoromethylsulfonyl)imide Room-Temperature Ionic Liquids: A Quest for the Structure–Property Relationship

2021

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This study explores the transport properties of bis(trifluoromethylsulfonyl)imide-based ionic liquids with a naturally derived (1 R ,2 S ,5 R )-(−)-menthol moiety in the cationic part. In particular, we investigated the dependence of the dynamic viscosity and electrical conductivity as functions of the alkyl chain length. An important finding of this study is that both properties show nonmonotonic behavior with respect to the alkyl chain length. The nonmonotonic dependency is an obstacle for establishing the relationships between the structure and transport properties of homologues. To overcome this difficulty, we recommend fast property screening using a theoretical model that we developed, which allows for efficient viscosity prediction by means of the group contribution method. As demonstrated in this study, the model allows for reliable predictions of viscosity in the studied series with an overall relative deviation of less than 8%.

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Chiral protic imidazolium salts with a (−)-menthol fragment in the cation: synthesis, properties and use in the Diels–Alder reaction

Abstract: New chiral protic imidazolium salts from a natural (−)-menthol, their physicochemical properties and catalytic activity in a Diels–Alder reaction.

Cited by 13 publications

References 41 publications

On the Miscibility of Nematic Liquid Crystals with Ionic Liquids and Joint Reaction for High Helical Twisting Power Product(s)

On the Miscibility of Nematic Liquid Crystals with Ionic Liquids and Joint Reaction for High Helical Twisting Power Product(s)

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

On the Influence of the Menthol Moiety on the Transport Properties of a Homologue Series of Functionalized Bis(trifluoromethylsulfonyl)imide Room-Temperature Ionic Liquids: A Quest for the Structure–Property Relationship

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