A New Proton Conductive Liquid with No Ions: Pseudo‐Protic Ionic Liquids

Doi, Hiroyuki; Song, Xuedan; Minofar, Babak; Kanzaki, Ryo; Takamuku, Toshiyuki; Umebayashi, Yasuhiro

doi:10.1002/chem.201302228

Cited by 65 publications

(78 citation statements)

References 63 publications

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“…In the case of pure HTf 2 N, its signal for 19 F appeared at -76.0 ppm. 36 This indicates that 19 [10][11][12] the Grotthuss-like conduction of H + is promoted by dilution, while ligands move faster when they are added to common solvate ILs. 24 Consequently, in terms of the effect of dilution, the hydronium solvate IL is distinguished not only from protic ILs but also from the previously reported solvate ILs.…”

Section: The Formation Of [H 3 O + •18c6mentioning

confidence: 99%

Suppression of Fast Proton Conduction by Dilution of a Hydronium Solvate Ionic Liquid: Localization of Ligand Exchange

Kawata

Kitada

Tsuchida

et al. 2020

J. Electrochem. Soc.

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A dilution effect on the proton conduction of a hydronium solvate ionic liquid [H 3 O + •18C6]Tf 2 N, which consists of hydronium ion (H 3 O +), 18-crown-6-ether ligand (18C6), and bis[(trifluoromethyl)sulfonyl]amide anion (Tf 2 N-; Tf = CF 3 SO 2), has been studied. When [H 3 O + •18C6]Tf 2 N was diluted using equimolar 18C6 solvent, the distinctive fast proton conduction in [H 3 O + •18C6]Tf 2 N was suppressed in stark contrast to the case of common protic ionic liquids. Nuclear magnetic resonance spectroscopy showed that the fast exchange between free 18C6 molecules and coordinated ones, suggesting that the added solvent had induced a local proton exchange rather than a cooperative proton relay.

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Section: The Formation Of [H 3 O + •18c6mentioning

confidence: 99%

Suppression of Fast Proton Conduction by Dilution of a Hydronium Solvate Ionic Liquid: Localization of Ligand Exchange

Kawata

Kitada

Tsuchida

et al. 2020

J. Electrochem. Soc.

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“…MacFarlane and Seddon [24] proposed a limit of a 1% neutral species presence in an ionic liquid to be called 'pure ionic liquid'. The term pseudo-protic ionic liquid was suggested by Doi et al [25] after they discovered that a mixture of N-methylimidazole and acetic acid exhibited electrical conductivity behavior even though the mixture was mostly dominated by neutral species rather than ions when inspected using Raman spectroscopy.…”

Section: Introductionmentioning

confidence: 99%

Thermophysical Properties and CO2 Absorption of Ammonium-Based Protic Ionic Liquids Containing Acetate and Butyrate Anions

et al. 2019

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Ionic liquids, which are classified as new solvents, have been identified to be potential solvents in the application of CO2 capture. In this work, six ammonium-based protic ionic liquids, containing ethanolammonium [EtOHA], tributylammonium [TBA], bis(2-ethylhexyl)ammonium [BEHA] cations, and acetate [AC] and butyrate [BA] anions, were synthesized and characterized. The thermophysical properties of the ammonium-based protic ionic liquids were measured. Density, , and dynamic viscosity, , were determined at temperatures between 293.15 K and 363.15 K. The density and viscosity values were correlated using empirical correlations and the thermal coefficient expansion, p, and molecular volume, Vm, were estimated using density values. The thermal stability of the ammonium-based protic ionic liquids was investigated using thermogravimetric analyzer (TGA) at a heating rate of 10 C.min‒1. The CO2 absorption of the ammonium-based ionic liquids were measured up to 20 bar at 298.15 K. From the experimental results, [BEHA][BA] had the highest affinity towards CO2 with the mol fraction of CO2 absorbed approaching 0.5 at 20 bar. Generally, ionic liquids with butyrate anions have better CO2 absorption than that of acetate anions while [BEHA] ionic liquids have higher affinity towards CO2 followed by [TBA] and [EtOHA] ionic liquids.

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“…Although the ΔpK a is better as the solvent parameter for not only the inter-ionic interactions in PIL but also various static/dynamic macroscopic properties of PIL, the auto-protolysis constant K s could be more suitable for representing the acid-base property as they are determined on the basis of directly measured pH in PIL [54][55][56]. Although the ΔpK a is better as the solvent parameter for not only the inter-ionic interactions in PIL but also various static/dynamic macroscopic properties of PIL, the auto-protolysis constant K s could be more suitable for representing the acid-base property as they are determined on the basis of directly measured pH in PIL [54][55][56].…”

Section: Introductionmentioning

confidence: 99%

Hydrogen bond in imidazolium based protic and aprotic ionic liquids

Watanabe

Doi

Saito

et al. 2016

Journal of Molecular Liquids

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a b s t r a c t Keywords:Hydrogen bond Protic ionic liquids X-ray scattering MD simulations Liquid structure of bis-(trifluoromethanesulfonyl)amide TFSA − based protic and aprotic ionic liquids composed of imidazolium [h 2 Im + ], N-methylimidazolium [C 1 hIm + ] and N,N'-dimethylimidazolium [C 1 mIm + ] were investigated by high-energy total scattering (HETS) experiments. The nearest neighboring cation-anon orientation variations by the N-methyl groups substitution to proton were suggested based on the peaks at around 6 and 9 Å in the differential radial distribution functions as the form of r 2 {G X-ray (r) -1} for these ionic liquids. It was supposed that the NH · · · O hydrogen bond causes the cation-anion orientation variations. To obtain further insight into the hydrogen bond in the PIL, MD simulations performed and agreed well with the experiments. According to spatial distribution functions (SDF) for the three ionic liquids, the O atom of TFSA − prefers the NH hydrogen of the imidazolium that has the most positive partial atomic charge in the cation, while the F atom locates right above and right below the imidazolium ring plane. In addition, the NH · · · O hydrogen bond has short bond lengths and linear bond angles, while the C 2 H · ·O interaction is long and bent. The NH · · · O hydrogen bond in the PIL was discussed based on structural aspect accompanied by a thermodynamic viewpoint.

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A New Proton Conductive Liquid with No Ions: Pseudo‐Protic Ionic Liquids

Cited by 65 publications

References 63 publications

Suppression of Fast Proton Conduction by Dilution of a Hydronium Solvate Ionic Liquid: Localization of Ligand Exchange

Suppression of Fast Proton Conduction by Dilution of a Hydronium Solvate Ionic Liquid: Localization of Ligand Exchange

Thermophysical Properties and CO2 Absorption of Ammonium-Based Protic Ionic Liquids Containing Acetate and Butyrate Anions

Hydrogen bond in imidazolium based protic and aprotic ionic liquids

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