Browse
Submit Data
Databases
API
Help

Dataset Information

40 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis and Physical Properties of Tunable Aryl Alkyl Ionic Liquids (TAAILs).

ABSTRACT: Tunable aryl alkyl ionic liquids (TAAILs) based on the imidazolium cation were first reported in 2009. Since then, a series of TAAILs with different properties due to the electron-donating or -withdrawing effect of the substituents at the aryl ring has been developed. Herein, a wide variety of those ionic liquids (ILs) is presented in terms of their cation structure. The authors synthesized ILs containing the bromide or bis(trifluoromethane)sulfonimide anion and 1-aryl-3-alkyl imidazolium cations with various substituents in the ortho and/ or para position of the phenyl ring and alkyl chains of different lengths varying from butyl to dodecyl. The differences of their physical properties (melting point, thermal decomposition, viscosity, electro-chemical window) of these ILs are reported according to their structure.

SUBMITTER: Lerch S

PROVIDER: S-EPMC8596866 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Synthesis and Physical Properties of Tunable Aryl Alkyl Ionic Liquids (TAAILs).

Lerch Swantje S Strassner Thomas T

Chemistry (Weinheim an der Bergstrasse, Germany) 20211004 62

Tunable aryl alkyl ionic liquids (TAAILs) based on the imidazolium cation were first reported in 2009. Since then, a series of TAAILs with different properties due to the electron-donating or -withdrawing effect of the substituents at the aryl ring has been developed. Herein, a wide variety of those ionic liquids (ILs) is presented in terms of their cation structure. The authors synthesized ILs containing the bromide or bis(trifluoromethane)sulfonimide anion and 1-aryl-3-alkyl imidazolium cation ...[more]

PMID: 34608692

Similar Datasets

Friedel-Crafts acylation of benzene derivatives in tunable aryl alkyl ionic liquids (TAAILs).

Project description:An iron(III) chloride hexahydrate-catalyzed Friedel-Crafts acylation of benzene derivatives in tunable aryl alkyl ionic liquids (TAAILs) has been developed. Through optimization of the metal salt, reaction conditions and ionic liquids, we were able to design a robust catalyst system that tolerates different electron-rich substrates under ambient atmosphere and allows for a multigram scale.

| S-EPMC9972882 | biostudies-literature

Synthesis and Properties of Magnetic Aryl-Imidazolium Ionic Liquids with Dual Bronsted/Lewis Acidity.

Project description:A series of unique tunable aryl-imidazolium magnetic ionic liquids (MILs) with dual acidity that contain both Brønsted and Lewis acidic sites (abbreviated as B-L MILs) were synthesized and characterized using nuclear magnetic resonance and mass spectrometry. Physical properties, such as thermal properties, magnetic susceptibility, and Brønsted and Lewis acidity, were measured. These properties were found to depend on the cation structure. These B-L MILs had good solubility in many organic solvents, good thermal stability, and low melting points, and exhibited magnet-like behavior. For these B-L MILs, the Brønsted acidity was measured using ultraviolet-visible (UV-Vis), and the Lewis acidity was measured using Fourier transform infrared spectroscopy (FTIR). The results showed that B-L MILs with an electron-withdrawing group in the aryl-imidazolium moiety had higher Brønsted acidity, whereas those with an electron-donating group had higher Lewis acidity. This type of ionic liquid, with both Brønsted and Lewis acidic sites, is expected to be a useful solvent and catalyst for organic reactions.

| S-EPMC6316537 | biostudies-literature

Synthesis, Physical Properties and Application of a Series of New Polyoxometalate-Based Ionic Liquids.

Project description:This paper deals with the preparation and the characterization of four new ionic liquids resulting from the pairing of various polyoxotungstates or polyoxomolybdates with the cation trihexyltetradecylphosphonium. The physical properties measured by different techniques evidence that the viscosity and the rheological behaviors of such POM-based ionic liquids, POM-ILs, strongly depend on the nature of the POM, especially its charge. Playing on the nature of the POM, we can indeed obtain Newtonian liquids or some much more viscous materials exhibiting characteristics of resins or pseudo-plastics. In a second part of this study, the potentialities of using such materials both as solvent and catalyst for the oxidation of a series of alcohols are presented as proof of concept. This part highlights great differences in strength and selectivity as a function of the POM-IL used. Furthermore, a very simple way to recycle the catalyst is also presented.

| S-EPMC7831901 | biostudies-literature

Ionic Liquids Incorporating Polyamide 6: Miscibility and Physical Properties.

Project description:The effects of 1-vinyl-3-butyl imidazole chloride (VBIM) on the structure and properties of Polyamide 6 (PA6) were investigated systematically. It was found that PA6/VBIM blends were homogeneous without phase separation. The glass transition temperature (Tg) of PA6 increased with small VBIM loadings followed by the decreasing in Tg with further increasing the amount of VBIM. The crystallization temperature decreased with the addition of VBIM because of the strong interactions between VBIM and the PA6 matrix, as well as the dilution effect when large amounts of VBIM was introduced to the matrix. According to rheological testing, small amounts of VBIM enhanced the storage modulus and melt viscosity of PA6. Tensile tests also show an increase in strength and modulus at relatively low loadings of VBIM. The strength of PA6 with only 1 wt % VBIM improved by 108% compared to that of neat PA6. Fourier transform infrared (FTIR) investigations revealed that the ions of VBIM preferred to form hydrogen bonds with amide groups in PA6. Therefore, VBIM acts as physical connection point for the neighboring PA6 molecular chains. The specific interactions between VBIM and PA6 account not only for the enhanced melt viscosity of PA6, but also for the improved mechanical properties. Moreover, outstanding antistatic property was also observed. The surface resistivity of the sample with 1 wt % VBIM was 1.50 × 1010 Ω/sq, which means good electric dissipation property.

| S-EPMC6415449 | biostudies-literature

Tunable Aryl Alkyl Ionic Liquid Supported Synthesis of Platinum Nanoparticles and Their Catalytic Activity in the Hydrogen Evolution Reaction and in Hydrosilylation

Project description:Tunable aryl alkyl ionic liquids (TAAILs) are ionic liquids (ILs) with a 1-aryl-3-alkylimidazolium cation having differently substituted aryl groups. Herein, nine TAAILs with the bis(trifluoromethylsulfonyl)imide anion are utilized in combination with and without ethylene glycol (EG) as reaction media for the rapid microwave synthesis of platinum nanoparticles (Pt-NPs). TAAILs allow the synthesis of small NPs and are efficient solvents for microwave absorption. Transmission electron microscopy (TEM) shows that small primary NPs with sizes of 2 nm to 5 nm are obtained in TAAILs and EG/TAAIL mixtures. The Pt-NPs feature excellent activity as electrocatalysts in the hydrogen evolution reaction (HER) under acidic conditions, with an overpotential at a current density of 10 mA cm−2 as low as 32 mV vs the reversible hydrogen electrode (RHE), which is significantly lower than the standard Pt/C 20% with 42 mV. Pt-NPs obtained in TAAILs also achieved quantitative conversion in the hydrosilylation reaction of phenylacetylene with triethylsilane after just 5 min at 200 °C.

| S-EPMC9822459 | biostudies-literature

Synthesis and Physicochemical Properties of Acrylate Anion Based Ionic Liquids.

Project description:Two polymerizable ionic liquids (or monomeric ionic liquids, mILs) namely 1-butyl-3-methylimidazolium and choline acrylates ([C4mim]A and ChA, respectively) were synthesized using the modified Fukumoto method from corresponding chlorides. The chemical structure of the prepared mILs was confirmed with FTIR and NMR study. Investigation of the thermal properties with DSC demonstrates that both mILs have a Tg temperature of about 180 K and a melting point around 310 K. It was shown that the temperature dependence of FTIR confirm the Tg to be below 200. Both mILs exhibited non-Newtonian shear thinning rheological behavior at shear rates >4 s-1. It was shown that [C4mim]A is able to dissolve bacterial cellulose (BC) leading to a decrease in its degree of polymerization and recrystallisation upon regeneration with water; although in the ChA, the crystalline structure and nanofibrous morphology of BC was preserved. It was demonstrated that the thixotropic and rheological properties of cellulose dispersion in ChA at room temperature makes this system a prospective ink for 3D printing with subsequent UV-curing. The 3D printed filaments based on ChA, containing 2 wt% of BC, and 1% of N,N'-methylenebisacrylamide after radical polymerization induced with 1% 2-hydroxy-2-methylpropiophenone, demonstrated Young's modulus 7.1 ± 1.0 MPa with 1.2 ± 0.1 MPa and 40 ± 5% of strength and ultimate elongation, respectively.

| S-EPMC9736722 | biostudies-literature

Synthesis and investigation of physico-chemical properties of dicationic ionic liquids.

Project description:A series of dicationic ionic liquids (ILs) including [C4(MIM)2][PF6]2, [C5(MIM)2][PF6]2, [C6(MIM)2][PF6]2 and [C4(PYR)2][PF6]2 were synthesized. Their thermal stability and melting points were analysed. It was found that dicationic ILs presented important implications in the design of homogeneous and heterogeneous system with water. A homogeneous system of dicationic ILs with water could be formed at a relatively high temperature and then a heterogeneous system was formed when the solution was cooled to a low temperature. The ILs recovered by altering the temperature were obtained in high percentage yields of [C4(MIM)2][PF6]2 (97.6%), [C5(MIM)2][PF6]2 (97.3%), [C6(MIM)2][PF6]2 (98.0%) and [C4(PYR)2][PF6]2 (94.2%). On the other hand, [C4(MIM)2][PF6]2 and [C5(MIM)2][PF6]2 exhibited good solubility in acetonitrile and acetone. A homogeneous system could be achieved with imidazolium-based ILs with a relatively low amount of water and acetonitrile at room temperature. All of the properties of dicationic ILs have a strong correlation with the nature of dications, the linkage chain and the symmetry of dications. Dicationic ILs may provide a new opportunity for some specific applications in order to enable the effective separation and isolation of products.

| S-EPMC6304111 | biostudies-literature

The Nanostructure of Alkyl-Sulfonate Ionic Liquids: Two 1-Alkyl-3-methylimidazolium Alkyl-Sulfonate Homologous Series.

Project description:The functionalization of polymers with sulfonate groups has many important uses, ranging from biomedical applications to detergency properties used in oil-recovery processes. In this work, several ionic liquids (ILs) combining 1-alkyl-3-methylimidazolium cations [CnC1im]+ (4 ≤ n ≤ 8) with alkyl-sulfonate anions [CmSO3]- (4 ≤ m ≤ 8) have been studied using molecular dynamics simulations, totalizing nine ionic liquids belonging to two homologous series. The radial distribution functions, structure factors, aggregation analyses, and spatial distribution functions reveal that the increase in aliphatic chain length induces no significant change in the structure of the polar network of the ILs. However, for imidazolium cations and sulfonate anions with shorter alkyl chains, the nonpolar organization is conditioned by the forces acting on the polar domains, namely, electrostatic interactions and hydrogen bonding.

| S-EPMC10004415 | biostudies-literature

Synthesis and biological properties of a series of aryl alkyl disulfide derivatives.

Project description:Disulfide containing compounds are recognized for their wide range of biological properties and are known for their important applications in the pharmaceutical field. In this study, a series of diaryl disulfides with varying alkyl chain length (C8-C16) was synthesized and assessed for their physicochemical and biological properties. The interactions of compounds with bovine serum albumin (BSA) was investigated in order to study their ability to bind with blood serum protein. An increase in the binding constants (Ka) was observed with increasing chain length C8-C12, while a decrease in value was obtained with compounds of chain length C14 and C16 showing a cut off effect at C12. The thermodynamic parameters of binding indicated that the compounds bound to BSA mostly by van der Waals forces and hydrogen bonding. Molecular docking studies showed that the diaryl disulfides displayed greater binding affinity to Trp 213 rather than the Trp 134 residue on the BSA molecule. The trend observed in molecular docking is in line with the fluorescence binding studies whereby the C12 derivative was found to show optimum affinity with BSA. The disulfide with chain length C10 showed moderate antibacterial activity the highest inhibitory activity against Bacillus cereus. The cytotoxicity of the disulfides towards HaCaT cells decreased from C8 to C14. The overall results obtained show that these disulfides have potent antibacterial properties against Gram-positive bacteria Bacillus cereus at concentrations which are relatively non-toxic to normal cells.

| S-EPMC7644900 | biostudies-literature

Ge-Fe Carbonyl Cluster Compounds: Ionic Liquids-Based Synthesis, Structures, and Properties.

Project description:Nine Ge-Fe carbonyl cluster compounds are prepared via ionic liquids-based synthesis. This includes the novel compounds [EMIm][Fe(CO)3 I(GeI3 )], [EHIm][Fe(CO)3 I(GeI3 )], [BMIm][GeI2 {Fe(CO)4 }2 (μ-I)][AlCl4 ]2 , [GeI2 {Fe(CO)4 }2 (μ-I)][Fe(AlBr4 )3 ], [BMIm]2 [(FeI2 )0.75 {Fe(CO)2 I(GeI3 )2 }2 ], and [EHIm][Fe(CO)4 (GeI2 )2 Fe(CO)3 GeI3 ] as well as the previously reported compounds (Fe(CO)4 (GeI3 )2 , FeI4 {GeI3 Fe(CO)3 }2 , and Ge12 {Fe(CO)3 }8 (μ-I)4 (EMIm: 1-ethyl-3-methylimidazolium, EHIm: 1-ethylimidazolium, BMIm: 1-butyl-3-methylimidazolium). With this series of compounds, a comparison of synthesis conditions and structural features is possible and, for instance, allows correlating the composition and structure of the respective Ge-Fe carbonyl cluster compounds with the type and acidity of the ionic liquid. With [EMIm][{GeI3 }2 Fe(CO)3 I], moreover, we can exemplarily show the thermal decomposition as a single-source precursor in the ionic liquid, resulting in bimetallic Ge-Fe nanoparticles with small size and narrow size distribution (7.0±1.4 nm).

| S-EPMC7874258 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data