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A New Class of Task-Specific Imidazolium Salts and Ionic Liquids and Their Corresponding Transition-Metal Complexes for Immobilization on Electrochemically Active Surfaces.

ABSTRACT: Adding to the versatile class of ionic liquids, we report the detailed structure and property analysis of a new class of asymmetrically substituted imidazolium salts, offering interesting thermal characteristics, such as liquid crystalline behavior, polymorphism or glass transitions. A scalable general synthetic procedure for N-polyaryl-N'-alkyl-functionalized imidazolium salts with para-substituted linker (L) moieties at the aryl chain, namely [LPh_m Im^H R]⁺ (L=Br, CN, SMe, CO₂ Et, OH; m=2, 3; R=C₁₂ , PEG_n ; n=2, 3, 4), was developed. These imidazolium salts were studied by single-crystal X-ray diffraction (SC-XRD), NMR spectroscopy and thermochemical methods (DSC, TGA). Furthermore, these imidazolium salts were used as N-heterocyclic carbene (NHC) ligand precursors for mononuclear, first-row transition metal complexes (Mn^II , Fe^II , Co^II , Ni^II , Zn^II , Cu^I , Ag^I , Au^I ) and for the dinuclear Ti-supported Fe-NHC complex [(OPy)₂ Ti(OPh₂ ImC₁₂ )₂ (FeI₂ )] (OPy=pyridin-2-ylmethanolate). The complexes were studied concerning their structural and magnetic behavior via multi-nuclear NMR spectroscopy, SC-XRD analyses, variable temperature and field-dependent (VT-VF) SQUID magnetization methods, X-band EPR spectroscopy and, where appropriate, zero-field ⁵⁷ Fe Mössbauer spectroscopy.

SUBMITTER: Seidl V

PROVIDER: S-EPMC9315159 | biostudies-literature |

REPOSITORIES: biostudies-literature

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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

Transcriptional toxicity of imidazolium- and cholinium-based ionic liquids

Project description:Transcriptional toxicity of imidazolium- and cholinium-based ionic liquids

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Biodegradation of imidazolium ionic liquids by activated sludge microorganisms.

Project description:Biological properties of ionic liquids (ILs) have been usually tested with the help of standard biodegradation or ecotoxicity tests. So far, several articles on the identification of intermediate metabolites of microbiological decay of ILs have been published. Simultaneously, the number of novel ILs with unrecognized characteristics regarding biodegradability and effect on organisms and environment is still increasing. In this work, seven imidazolium ionic liquids of different chemical structure were studied. Three of them are 1-alkyl-3-methyl-imidazolium bromides, while the other four are tetra- or completely substituted imidazolium iodides. This study focused on the identification of intermediate metabolites of the aforementioned ionic liquids subjected to biodegradation in a laboratory activated sludge system. Both fully substituted ionic liquids and 1-ethyl-3-methyl-imidazolium bromide were barely biodegradable. In the case of two of them, no biotransformation products were detected. The elongation of the alkyl side chain made the IL more susceptible for microbiological decomposition. 1-Decyl-3-methyl-imidazolium bromide was biotransformed most easily. Its primary biodegradation up to 100 % could be achieved. Nevertheless, the cleavage of the imidazolium ring has not been observed.

| S-EPMC4637002 | biostudies-literature

Imidazolium-based ionic liquids support biosimilar flavin electron transfer.

Project description:Understanding electron transport with electroactive microbes is key to engineering effective and scalable bio-electrochemical technologies. Much of this electron transfer occurs through small-molecule flavin mediators that perform one-electron transfers in abiotic systems but concerted two-electron transfer in biological systems, rendering abiotic systems less efficient. To boost efficiency, the principles guiding flavin electron transfer must be elucidated, necessitating a tunable system. Ionic liquids (ILs) offer such a platform due to their chemical diversity. In particular, imidazolium-containing ILs that resemble the amino acid histidine are bio-similar electrolytes that enable the study of flavin electron transfer. Using the model IL 1-ethyl-3-methylimidazolium ([Emim][BF4]), we observe concerted two-electron transfer between flavin mononucleotide and an unmodified glassy carbon electrode surface, while a one-electron transfer occurs in standard inorganic electrolytes. This work demonstrates the power of ILs to enable the mechanistic study of biological electron transfer, providing critical guidelines for improving electrochemical technologies based on these biological properties.

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Indium-Mediated Allylation of Carbonyl Compounds in Ionic Liquids: Effect of Salts in Ionic Liquids.

Project description:The In-mediated allylation of carbonyl compounds can be performed in various types of solvents including ionic liquids. However, we have found that in [bmim][BF?] (where bmim = 1-butyl-3-methylimidazolium), the In-mediated coupling of crotyl bromide with benzaldehyde gives a complex mixture, and some additives, such as halides and amines, are crucial for the successful conversion to the corresponding ?-adduct. Instead, the addition of alcohols or water promotes the formation of the ?-adduct. An asymmetric induction with up to 62% enantiomeric excess (ee) was observed employing cinchonidine as an additive in a binary solvent consisting of an ionic liquid and dichloromethane.

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Task-Specific Organic Salts and Ionic Liquids Binary Mixtures: A Combination to Obtain 5-Hydroxymethylfurfural From Carbohydrates.

Project description:The increase in energy demand and depletion of fossil fuels are among major issues of modern society. Valorization and transformation of raw materials in products of industrial value represent a challenge. This justifies the growing interest of scientific research toward the identification of suitable media and methodologies able to pursue above goals, paying attention to matter of sustainability. On this subject, we studied sulfonic-acid functionalized diimidazolium salts as catalysts for the conversion of fructose and sucrose to 5-hydroxymethylfurfural (5-HMF) in an ionic liquid mixture. In general, using these salts allowed us to obtain 5-HMF in good yields from both substrates in mild conditions. Indeed, at 60°C and in the presence of 20 mol% of catalyst, 5-HMF yields of 60 and 30% were obtained from fructose and sucrose, respectively. The catalytic system was recycled and used up to six times observing no appreciable loss in yield for the first four cycles. Moreover, we gathered mechanistic information by in situ 1H NMR monitoring the dehydration of fructose. To dissect the role of acidity on the reaction, we determined the Hammett acidity function of each salt. Comparison of these results with yields and reactivity observed in the presence of related monocationic salts and with a dicationic salt bearing only one sulfonic acid group, allowed stating that the reactivity observed is the result of the combined action of acidity and structural features of the catalysts. Overall, the approach proposed here could contribute to pave the way to increase sustainability in the raw material valorization processes.

| S-EPMC6437106 | biostudies-literature

Unexpected Intrinsic Lability of Thiol-Functionalized Carboxylate Imidazolium Ionic Liquids.

Project description:New thiol-functionalized carboxylate ionic liquids (ILs), varying both for the cation and for the anion structures, have been prepared as new potential redox switching systems by reacting either 3-mercapto propionic acid (3-MPA) or N-acetyl-cysteine (NAC) with commercially available methyl carbonate ILs. Different ratios of thiol/disulfide ILs were obtained depending both on the acid employed in the neutralization reaction and on the reaction conditions used. Surprisingly, the imidazolium ILs displayed limited thermal stability which resulted in the formation of an imidazole 2-thione and a new sulfide ionic liquid. Conversely, the formation of the imidazole 2-thione was not observed when phosphonium disulfide ILs were heated, thus confirming the involvement of the imidazolium ring in an unexpected side reaction. An insight into the mechanism of the decomposition has been provided by means of DFT calculations.

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Multifunctional Characteristics of Carbon Fibers Modified with Imidazolium Ionic Liquids.

Project description:A multifunctional designing approach is of great importance for advanced composite applications. This study assessed the use of ionic liquids (ILs) to modify the surface of carbon fiber (CF) and impart multifunctional characteristics to it. For that, ethanolic solutions of different ILs, 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, 1-butyl-3-methylimidazolium chloride and 1-(2-hydroxyethyl)-3-methylimidazolium chloride, at different concentrations, were used to treat the CF. Fourier-transform infrared spectroscopy confirmed the presence of IL on the CF surface. The contact angle for 1% w/v IL-treated CF and DGEBA epoxy decreased by up to 35%, corresponding to an increase in surface energy of fiber, accompanied by an increase of 91% in interfacial shear strength. These enhancements were achieved with the hydroxy-functionalized IL, showing the tunability of CF properties through the N-imidazolium substituent. An increase in crystallite size along the basal plane was also found due to the ordering of the graphitic structure on the surface. Moreover, there was a decrease in electrical resistivity of 77%. In all, the imidazolium ILs were considered a promising approach to induce multifunctional characteristics, namely enhanced interfacial strength and electrical conductivity, to unsized CF, which can also be beneficial for recycled fibers without deteriorating their inherent surface properties.

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Stable and Oriented Liquid Crystal Droplets Stabilized by Imidazolium Ionic Liquids.

Project description:Liquid crystals represent a fascinating intermediate state of matter, with dynamic yet organized molecular features and untapped opportunities in sensing. Several works report the use of liquid crystal droplets formed by microfluidics and stabilized by surfactants such as sodium dodecyl sulfate (SDS). In this work, we explore, for the first time, the potential of surface-active ionic liquids of the imidazolium family as surfactants to generate in high yield, stable and oriented liquid crystal droplets. Our results show that [C12MIM][Cl], in particular, yields stable, uniform and monodisperse droplets (diameter 74 ± 6 µm; PDI = 8%) with the liquid crystal in a radial configuration, even when compared with the standard SDS surfactant. These findings reveal an additional application for ionic liquids in the field of soft matter.

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Structural Reorganization of Imidazolium Ionic Liquids Induced by Pressure-Enhanced Ionic Liquid-Polyethylene Oxide Interactions.

Project description:Mixtures of polyethylene oxide (PEO, M.W.~900,000) and imidazolium ionic liquids (ILs) are studied using high-pressure Fourier-transform infrared spectroscopy. At ambient pressure, the spectral features in the C-H stretching region reveal that PEO can disturb the local structures of the imidazolium rings of [BMIM]+ and [HMIM]+. The pressure-induced phase transition of pure 1-butyl-3-methylimidazolium bromide ([BMIM]Br) is observed at a pressure of 0.4 GPa. Pressure-enhanced [BMIM]Br-PEO interactions may assist PEO in dividing [BMIM]Br clusters to hinder the aggregation of [BMIM]Br under high pressures. The C-H absorptions of pure 1-hexyl-3-methylimidazolium bromide [HMIM]Br do not show band narrowing under high pressures, as observed for pure [BMIM]Br. The band narrowing of C-H peaks is observed at 1.5 GPa for the [HMIM]Br-PEO mixture containing 80 wt% of [HMIM]Br. The presence of PEO may reorganize [HMIM]Br clusters into a semi-crystalline network under high pressures. The differences in aggregation states for ambient-pressure phase and high-pressure phase may suggest the potential of [HMIM]Br-PEO (M.W.~900,000) for serving as optical or electronic switches.

| S-EPMC7835789 | biostudies-literature

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