Cation-fluorinated ionic liquids: Synthesis, physicochemical properties and comparison with non-fluorinated analogues

Abafe, Onajite T. Diejomaoh; Azim, Muhammad Mohsin; Martincigh, Bice S.; Stark, Annegret

doi:10.1016/j.molliq.2021.118104

Cited by 9 publications

(12 citation statements)

References 60 publications

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“…This observation aligns with prior research investigating the NMR chemical shifts of FILs with halide and sulfonamide counterions. 13 These data support site-specific interactions of both fluorinated anions and the iodide counterion with the imidazolium core protons, particularly the C2 proton, while also demonstrating reduced interionic interactions with an increase in alkyl chain length.…”

Section: Design and Synthesis Of Filssupporting

confidence: 55%

“…N-methylimidazole (99%), isopropanol, 1H,1H,2H,2H-perfluorooctyl iodide (97%), and 1H,1H,2H,2H-perfluorohexyl iodide (97%) were purchased from Fisher Scientific. Lithium bis(trifluoromethanesulfonyl)imide (99.9%), sodium metal (in mineral oil, 99.9%), graphite, sulfuric acid (H 2 SO 4 , 95.0−98.0%), potassium permanganate (KMNO 4 , 99.0%), acetone (99.5%), ethylenediamine (EDA, 99%), propylamine (98%), m-xylylene diisocyanate (mXDI, 13 C, and 19 F nuclear magnetic resonance (NMR) spectroscopy was carried out using a Bruker Avance NEO 400 MHz NMR spectrometer using (CD 3 ) 2 SO (DMSO-d 6 ) as the solvent, with nondeuterated DMSO as a chemical shift standard. The purity of compounds was determined via C, H, N, and F elemental analysis performed at Atlantic Microlabs.…”

Section: Methodsmentioning

confidence: 99%

“…14,16,18,20 For example, Abafe et al investigated ILs of 1H, 1H, 2H, 2H-perfluorooctyl imidazolium cations with anions, such as Tf 2 N, OTf, acetate (OAc), and halides, examining the influence of cation fluorination on density, viscosity, and refractive index. 13 Their findings indicate that FILs exhibit elevated densities and viscosities but decreased refractive indices in comparison to their nonfluorinated counterparts, with viscosity and refractive index being anion-dependent and increasing in the order Tf 2 N < OTf < OAc. The authors attributed this to a combination of spatial constraints imposed by the fluoroalkyl chains and the increased interactions established between the fluorinated groups and various anions.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Characterization of Fluorinated Ionic Liquids and Their Application in Hydrofluorocarbon Gas Uptake

Pulukkody,

Baca,

Lak

et al. 2024

Ind. Eng. Chem. Res.

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This study reports the synthesis and comprehensive characterization of five fluorinated ionic liquids (FILs), each composed of an imidazolium cation of varied fluoroalkyl chain lengths paired with a fluorinated anion: a newly developed aromatic sulfonamide, bistriflimide (Tf 2 N), or iodide. The relationship between molecular structure and physical properties, including thermal behavior, density, and viscosity, is reported. The identity of the anion has the strongest effect on both thermal stability and thermal behavior, whereas elongation of the fluorinated alkyl chain of the cation more strongly influences density and viscosity. These observations suggest nanosegregation within the liquid and the formation of three microphases (polar, nonpolar, and fluorous). We then evaluate the solubilities of commonly used hydrofluorocarbon refrigerant gases, HFC-32 (difluoromethane) and HFC-125 (pentafluoroethane), in the neat and encapsulated FILs, comparing their performance against commercially available ionic liquids (ILs). We find higher solubilities of HFC-32 in the FILs relative to nonfluorinated commercial ILs that exhibited greater solubility of HFC-125, highlighting selective gas absorption. Additionally, we observe that encapsulated FILs exhibit trends in gas uptake analogous to those of neat FILs. This work not only contributes to a deeper understanding of the structure−property relationships in FILs but also presents promising avenues for their utilization in HFC gas uptake and separation processes, emphasizing the potential of encapsulated FILs as a viable technology to overcome challenges associated with high viscosities of ILs in bulk processing.

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Section: Design and Synthesis Of Filssupporting

confidence: 55%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and Characterization of Fluorinated Ionic Liquids and Their Application in Hydrofluorocarbon Gas Uptake

Pulukkody,

Baca,

Lak

et al. 2024

Ind. Eng. Chem. Res.

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“…According to refs , , bis(trifluoromethylsulfonyl)imide-based ionic liquids were obtained using anion exchange of 1,1,1-trifluoro- N -[(trifluoromethyl)sulfonyl]-methanesulfonamide lithium (LiTFSA) and chloride-based ionic liquids (VEL and VBL).…”

Section: Methodsmentioning

confidence: 99%

Experimental and DFT Studies on Electrochemical Performances of Ester-Containing Vinylimidazolium Ionic Liquids: Effect of the Ester Substituent and Anion

Deng

Shen

et al. 2023

J. Chem. Eng. Data

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Four imidazolium ionic liquids (ILs) with vinyl and ester groups were synthesized and characterized by 1H NMR, 13C NMR, and element analysis. The refractive index, electrical conductivity (EC), and electrochemical stability window (ESW) of the ILs were determined. The effect of the alkyl chain length of the ester group and anions on electrochemical properties was analyzed by density functional theory (DFT) calculations. At the same temperatures, the EC of the ILs decreased with the increase of the alkyl chain length. The ester group and vinyl group of cations showed a negative effect on the EC. The ESW increased with the increase of the alkyl chain length. The introduction of the ester group and vinyl group decreased the cathodic limiting potential of ester-based vinylimidazolium cations. DFT simulations showed that the structure of the IL was closely related to the EC and ESW. The average hydrogen bond length increased with the increase of the alkyl chain length of the ester group. The absolute interaction energy of ILs decreased with the increase of the alkyl chain length. Introduction of the vinyl group and ester group into the imidazolium cation resulted in a stronger cation–anion interaction, strengthening the ion mobility and charge transfer, resulting in a lower EC. The information is useful for the design and optimization of ILs as electrolytes for energy storage applications.

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“…50 From the data in Table S1 and Figure 4, it can be seen that the refractive index of [COC 4 mim][Tau] decreases linearly with the increase of water content, which is consistent with the trend of other functionalized ILs 33,40 non-functionalized ILs, 41 and as the temperature increases, the refractive index of [COC 4 mim]-[Tau] also gradually decreases, and this result is consistent with the results of the literature. 51 3.2. Volumetric Properties.…”

Section: Density Surface Tension and Refractive Indexmentioning

confidence: 99%

Thermodynamic Properties of Ether-Functionalized Ionic Liquids [COC₄mim][Tau]

Wu,

Wei,

Xuan

et al. 2024

J. Chem. Eng. Data

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The ether-functionalized ionic liquid 1-(4-methoxybutyl)-3-methylimidazolium taurine [COC 4 mim][Tau] was prepared and characterized. The density (ρ), surface tension (γ), and refractive index (n D ) were measured at 288.15−328.15 K using a standard addition method. The molar volume (V), standard entropy (S θ ), lattice energy (U lattice ), surface entropy (S a ), surface energy (E a ), and molar surface Gibbs free energy (G m,s) were calculated using the density and surface tension data. By refractive index data, the degree of molar polarization (R m ), molar polarizability (α p ), and its surface tension (γ pre ) were predicted. The results showed that its predicted value was highly similar to the measured value. Then, the variation of vapor pressure (p) of [COC 4 mim][Tau] with temperature was discussed using thermogravimetric analysis of experimental data. It was found that p increased exponentially with temperature, and compared to low temperature, a high temperature is more conducive to the increase of p for [COC 4 mim][Tau]. The enthalpy of vaporization (Δ l g H m θ (T av )) at average temperature (T av ) was calculated by combining the Langmuir equation with the Clausius−Clapeyron equation, and it was converted into the enthalpy of vaporization (Δ l g H m θ (298.15)) at ambient temperature (298.15). It is hoped that these thermodynamic properties data can provide a theoretical basis for the subsequent research.

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Cation-fluorinated ionic liquids: Synthesis, physicochemical properties and comparison with non-fluorinated analogues

Cited by 9 publications

References 60 publications

Synthesis and Characterization of Fluorinated Ionic Liquids and Their Application in Hydrofluorocarbon Gas Uptake

Synthesis and Characterization of Fluorinated Ionic Liquids and Their Application in Hydrofluorocarbon Gas Uptake

Experimental and DFT Studies on Electrochemical Performances of Ester-Containing Vinylimidazolium Ionic Liquids: Effect of the Ester Substituent and Anion

Thermodynamic Properties of Ether-Functionalized Ionic Liquids [COC₄mim][Tau]

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Cation-fluorinated ionic liquids: Synthesis, physicochemical properties and comparison with non-fluorinated analogues

Cited by 9 publications

References 60 publications

Synthesis and Characterization of Fluorinated Ionic Liquids and Their Application in Hydrofluorocarbon Gas Uptake

Synthesis and Characterization of Fluorinated Ionic Liquids and Their Application in Hydrofluorocarbon Gas Uptake

Experimental and DFT Studies on Electrochemical Performances of Ester-Containing Vinylimidazolium Ionic Liquids: Effect of the Ester Substituent and Anion

Thermodynamic Properties of Ether-Functionalized Ionic Liquids [COC4mim][Tau]

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Thermodynamic Properties of Ether-Functionalized Ionic Liquids [COC₄mim][Tau]