Browse
Submit Data
Databases
API
Help

Dataset Information

7 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Facile Synthesis of Tetra-Branched Tetraimidazolium and Tetrapyrrolidinium Ionic Liquids.

ABSTRACT: A facile synthetic route for tetra-branched tetraimidazolium and tetrapyrrolidinium ionic liquids was developed. In contrast to the previous synthetic scheme, the new synthetic route requires only three reaction steps instead of seven. The total yield of tetracation was also improved from 17-21 to 39-41%. Using the new synthetic scheme, four kinds of tetracations were synthesized from the combination of two cationic units (imidazolium and pyrrolidinium) and two counteranions [bis(fluorosulfonyl)imide (FSI) and bis(trifluoromethanesulfonyl)imide (TFSI)]. Basic physical properties including glass transition temperature, thermal decomposition temperature, density, viscosity, and ionic conductivity were determined. The counterion exchange from TFSI to FSI resulted in lower glass transition temperature and higher ionic conductivity. Tetrapyrrolidinium exhibited higher viscosity and lower ionic conductivity than tetraimidazolium. The counterion exchange from TFSI to FSI resulted in lower viscosity in the case of tetraimidazolium, while the opposite result was obtained in the case of tetrapyrrolidinium. Tetracations composed of ethyl imidazolium units, diethylene glycol spacers, and FSI counterions exhibited the highest ionic conductivity of 3.5 × 10^-4 S cm^-1 at 25 °C under anhydrous conditions. This is the best ionic conductivity in the tetracations ever reported.

SUBMITTER: Ikeda T

PROVIDER: S-EPMC8340402 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Tetrahydrothiophene-Based Ionic Liquids: Synthesis and Thermodynamic Characterizations.

Project description:S-alkyltetrahydrothiophenium, [Cn THT]+ bis(trifluorosulfonyl)imide, [NTf2 ]- room temperature ionic liquids (ILs) and tetraphenylborate, [BPh4 ]- salts with alkyl chain lengths from C4 to C10 have been prepared. The ILs and salts were characterized and their purity verified by 1 H- and 13 C-nuclear magnetic resonance, elemental analysis, ion chromatography, Karl-Fischer titration, single crystal X-ray diffraction as well as thermogravimetric analysis. The experimentally determined density and viscosity decrease with increasing temperature. The experimental solubility of the [Cn THT][NTf2 ]-ILs in water (75 to 2.2 mg/L for C4 to C10 ) was modelled with very good agreement by Perturbed Chain Statistical Associating Fluid Theory (PC-SAFT), based on the extremely low vapor pressures for the [Cn THT][NTf2 ]-ILs measured in this work (4.15 to 0.037 ⋅ 10-7 ×psat for C4 to C10 ). PC-SAFT is able to predict and correlate different thermodynamic properties by estimating the Helmholtz residual energy.

| S-EPMC7874261 | biostudies-literature

Transcriptional toxicity of imidazolium- and cholinium-based ionic liquids

Project description:Ionic Liquids are a broad group of salts with low melting points that can be specifically tuned for a broad range of applications. Despite being initially considered “green” solvents, their better environmental friendliness compared to traditional solvents has been increasingly challenged. In this study, we aimed to investigate the molecular effects of ILs exposure by using RNA-sequencing to study differential gene expression patterns. Thus, we exposed Daphnia magna to 1-ethyl-3-methylimidazolium chloride ([C2mim]Cl), 1-dodecyl chloride-3-methylimidazolium ([C12mim]Cl) and cholinium chloride ([Chol]Cl). Results suggest that the three ILs share several mechanisms of toxicity, including cellular membrane and cytoskeleton damage, oxidative stress, inhibition of antioxidant enzymes, mitochondrial affectation, changes in protein biosynthesis and energy production, DNA damage, and ultimately, programmed cell death and disease initiation. Overall, the dataset revealed that [C2mim]Cl and [C12mim]Cl were, respectively, the least and the most toxic ILs at the transcriptional level. Also, it is reinforced that [Chol]Cl is not devoid of environmental hazardous potential. Unique gene expression signatures could also be identified for each IL.

2021-08-13 | GSE156769 | GEO

Synthesis of Purine-Based Ionic Liquids and Their Applications.

Project description:Bio-based ionic liquids (ILs) are being increasingly sought after, as they are more sustainable and eco-friendly. Purines are the most widely distributed, naturally occurring N-heterocycles, but their low water-solubility limits their application. In this work, four purines (theobromine, theophylline, xanthine, and uric acid) were combined with the cation tetrabutylammonium to synthesize bio-based ILs. The physico-chemical properties of the purine-based ILs were characterized, including their melting and decomposition temperatures and water-solubility. The ecotoxicity against the microalgae Raphidocelis subcapitata was also determined. The ILs show good thermal stability (>457 K) and an aqueous solubility enhancement ranging from 53- to 870-fold, in comparison to their respective purine percursors, unlocking new prospects for their application where aqueous solutions are demanded. The ecotoxicity of these ILs seems to be dominated by the cation, and it is similar to chloride-based IL, emphasizing that the use of natural anions does not necessarily translate to more benign ILs. The application of the novel ILs in the formation of aqueous biphasic systems (ABS), and as solubility enhancers, was also evaluated. The ILs were able to form ABS with sodium sulfate and tripotassium citrate salts. The development of thermoresponsive ABS, using sodium sulfate as a salting-out agent, was accomplished, with the ILs having different thermosensitivities. In addition, the purine-based ILs acted as solubility enhancers of ferulic acid in aqueous solution.

| S-EPMC8620494 | biostudies-literature

Metal Assisted Synthesis of Cationic Sulfidobismuth Cubanes in Ionic Liquids.

Project description:Bi2 S3 was dissolved in the presence of either AuCl/PtCl2 or AgCl in the ionic liquids [BMIm]Cl ⋅ xAlCl3 (BMIm=1-n-butyl-3-methylimidazolium; x=4-4.3) through annealing the mixtures at 180 or 200 °C. Upon cooling to room temperature, orange, air-sensitive crystals of [BMIm](Bi4 S4 )[AlCl4 ]5 (1) or Ag(Bi7 S8 )[S(AlCl3 )3 ]2 [AlCl4 ]2 (2) precipitated, respectively. 1 did not form in the absence of AuCl/PtCl2 , suggesting an essential role of the metal cations. X-ray diffraction on single-crystals of 1 revealed a monoclinic crystal structure that contains (Bi4 S4 )4+ heterocubanes and [AlCl4 ]- tetrahedra as well as [BMIm]+ cations. The intercalation of the ionic liquid was confirmed via solid state NMR spectroscopy, revealing unusual coupling behavior. The crystal structure of 2 consists of (Bi7 S8 )5+ spiro-dicubanes, [S(AlCl3 )3 ]2- tetrahedra triples, isolated [AlCl4 ]- tetrahedra, and heavily disordered silver(I) cations. No cation ordering took place in 2 upon slow cooling to 100 K.

| S-EPMC7874255 | biostudies-literature

Electrodialytic Universal Synthesis of Highly Pure and Mixed Ionic Liquids.

Project description:Ionic liquids (ILs) have attracted significant attention from researchers in various fields as a result of their unique properties. As new and important applications are identified for these materials, there is also a drive to develop methods for accessing a wider range of ILs. However, despite this demand, only a few techniques have so far been reported and, more importantly, general but efficient processes for IL synthesis have been lacking. Thus, it would be beneficial to devise a cost-effective, environmentally friendly means of producing a wide variety of pure ILs. The present work demonstrates a general purpose electrodialysis approach to the formation of highly pure ILs, based on the formation of nine different ILs from various combinations of cations and anions. In each case, the IL is obtained with a purity of greater than 99%. This method offers the advantages of avoiding the use of hazardous organic solvents and eliminating tedious and costly purification processes. Unlike conventional methods, this membrane-based technology also prevents the generation of side products. Mixed ILs have many potential applications, and the present technique readily generates various mixed ILs based on a simple adjustment of the applied current.

| S-EPMC9245113 | biostudies-literature

Ketoprofen-Based Ionic Liquids: Synthesis and Interactions with Bovine Serum Albumin.

Project description:The development of ionic liquids based on active pharmaceutical ingredients (API-ILs) is a possible solution to some of the problems of solid and/or hydrophobic drugs such as low solubility and bioavailability, polymorphism and an alternative route of administration could be suggested as compared to the classical drug. Here, we report for the first time the synthesis and detailed characterization of a series of ILs containing a cation amino acid esters and anion ketoprofen (KETO-ILs). The affinity and the binding mode of the KETO-ILs to bovine serum albumin (BSA) were assessed using fluorescence spectroscopy. All compounds bind in a distance not longer than 6.14 nm to the BSA fluorophores. The estimated binding constants (KA) are in order of 105 L mol-1, which is indicative of strong drug or IL-BSA interactions. With respect to the ketoprofen-BSA system, a stronger affinity of the ILs containing l-LeuOEt, l-ValOBu, and l-ValOEt cation towards BSA is clearly seen. Fourier transformed infrared spectroscopy experiments have shown that all studied compounds induced a rearrangement of the protein molecule upon binding, which is consistent with the suggested static mechanism of BSA fluorescence quenching and formation of complexes between BSA and the drugs. All tested compounds were safe for macrophages.

| S-EPMC6983093 | biostudies-literature

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

Project description: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.

| S-EPMC8596866 | 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

Cyclic phosphonium ionic liquids.

Project description:Ionic liquids (ILs) incorporating cyclic phosphonium cations are a novel category of materials. We report here on the synthesis and characterization of four new cyclic phosphonium bis(trifluoromethylsulfonyl)amide ILs with aliphatic and aromatic pendant groups. In addition to the syntheses of these novel materials, we report on a comparison of their properties with their ammonium congeners. These exemplars are slightly less conductive and have slightly smaller self-diffusion coefficients than their cyclic ammonium congeners.

| S-EPMC3944138 | biostudies-literature

Hydrogen Bonds in Disulfonic-Functionalized Acid Ionic Liquids for Efficient Biodiesel Synthesis.

Project description:Regulating the states of hydrogen bonds in ionic liquids (ILs) is an effective way to improve their catalytic performance. In this paper, disulfonic-functionalized acidic ionic liquids (DSFAILs) were synthesized successfully, including novel SO3H-functionalized binuclear IL (bis[3-(CH2)3SO3H-1-(CH2)2-Im][HSO4]2). For the biodiesel synthesis, compared with the traditional ILs catalysts, DSFAILs bis[(3-(CH2)3SO3H-1-(CH2)2-Im][HSO4]2, [Im(N (CH2)3SO3H)2][HSO4]) had higher catalytic activity even under mild reaction conditions. Using the density functional theory (DFT) method, the role of hydrogen bonds in different SO3H-functionalized acidic ionic liquids (SFAILs) was explored. The forms of hydrogen bonds existing in different ILs directly determine their acidity. It suggested that the forming status of the active sites (hydrogen bonds) were diverse in different SFAILs. Also, deep ionization of the hydrogen atoms from the cation-anion strong interaction could increase the acidity and catalytic performance of SFAILs. From this, the structure-activity relationship between the SFAILs structures and the catalytic activity of methyl oleate synthesis was proposed. Besides, the experimental results also showed that bis[3-(CH2)3SO3H-1-(CH2)2-Im][HSO4]2 catalyst had a high catalytic activity to obtain methyl oleate and the catalyst could be separated easily owing to its larger molecular weight. However, [Im(N(CH2)3SO3H)2][HSO4] had a stronger acidity and a lower steric hindrance and thus a higher catalytic activity and was the optimal catalyst for the methyl oleate synthesis. In the presence of a small amount of catalyst (6 wt %) and at low reaction temperature (353 K), the methyl oleate yield could reach up to 93%. After six recycles of the catalyst, the methyl oleate yield remained at 90%.

| S-EPMC7271023 | 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