- Aggregation behavior of zwitterionic surface active ionic liquids with different counterions, cations, and alkyl chains
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A group of zwitterionic surface active ionic liquids (SAILs) with different counterions, cations and alkyl chains, 3-(1-alkyl-3-imidazolio)propanesulfonate β-naphthalene sulfonate, (CnIPS-Nsa, n = 12, 14), 3-(1-dodecyl-3-imidazolio)propanesulfonate benzenesulfonate (C12IPS-Bsa), and dodecyl-N,N-dimethylammonio-3-propane sulfonate β-naphthalene sulfonate (SB-12-Nsa), were synthesized. Their aggregation behaviors in aqueous solutions were systematically investigated by surface tension, dynamic light scattering (DLS) and 1H NMR spectroscopy. Surface tension and DLS results illustrated that the surface properties, micelle size, and micellization behavior of zwitterionic SAILs in aqueous solutions are significantly affected by the anion type, anionic structure and the hydrophobicity of the alkyl chain. The SAILs with more hydrophobic anions and long alkyl chains are expected to favor the micellization. The steric hindrance and hydrophobicity of the cations, as well as the binding strength of the cations with the anions, also play important roles in the aggregation of zwitterionic SAILs. Additionally, the micelle formation mechanism was acquired by detailed analysis of the 1H NMR spectra. The existence of π-π stacking between imidazolium and counterions was proved. The enhanced π-π stacking and hydrophobic effect of Nsa- can promote the aggregation of zwitterionic SAILs. Density functional theory (DFT) calculations illustrated that the negative interaction energy of the complexes were C12IPS-Bsa/H2O > SB-12-Nsa/H2O > C12IPS-Nsa/H2O > C14IPS-Nsa/H2O. It is more difficult to form micelles in complexes with more negative interaction energy. The counterion electronegativity of Nsa- is smaller than that of Bsa-, which favors the formation of micelles.
- Sun, Panpan,Shi, Lijuan,Lu, Fei,Zheng, Liqiang
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- Supernucleophilic systems based on functionalized surfactants in the decomposition of 4-nitrophenyl esters derived from phosphorus and sulfur acids: I. Reactivity of a hydroxyimino derivative of gemini imidazolium surfactant
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A new functionalized gemini surfactant, 3,3′-[2-(hydroxyimino) propane-1,3-diyl]bis(1-dodecyl-1H-imidazol-3-ium) dichloride, and its non-micelle-forming methyl analog, were synthesized. Nucleophilicity of the oximate group in these compounds in the decomposition of 4-nitrophenyl esters derived from phosphorus and sulfur acids follows Bronsted relations for monomeric functionalized surfactants and non-micelle-forming oximes. As compared to the single-chained analog, the gemini surfactant ensured the same observed rate of substrate decomposition at lower concentration and lower pH. Micellar effects of the gemini surfactant in these reactions attain a value of ～103 and are determined mainly by substrate concentration in the micellar pseudophase.
- Kapitanov,Belousova,Shumeiko,Kostrikin,Prokop'Eva,Popov
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- Synthesis and assessment of new cationic gemini surfactants as inhibitors for carbon steel corrosion in oilfield water
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Three gemini surfactants were synthesized having the same length of terminal chain but differing in the spacer chain length and they were evaluated as corrosion inhibitors for carbon steel in oilfield water using weight loss, EIS, potentiodynamic polarization and open-circuit potential measurements. These measurements revealed that the synthesized materials have served as effective mixed-type corrosion inhibitors. Their adsorption on a carbon steel surface was well described by means of the Langmuir adsorption isotherm. The activation parameters for the dissolution of carbon steel in solutions of oilfield water in the absence and presence of these inhibitors were calculated. The effect of immersion time on the stability and durability of protective films adsorbed on a carbon steel surface was studied using weight loss method. Ex situ inspection, i.e. post-exposure analysis, for the treated carbon steel surface has been performed using SEM, EDX and FT-IR tools.
- El-Taib Heakal,Deyab,Osman,Nessim,Elkholy
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- Ionic conduction and dielectric response of poly(imidazolium acrylate) ionomers
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We use X-ray scattering to investigate morphology and dielectric spectroscopy to study ionic conduction and dielectric response of imidazolium-based single-ion conductors with two different counterions [hexafluorophosphate (PF6-) or bis(trifluoromethanesulfonyl)imide (F3CSO2NSO 2CF3- = Tf2N-)] with different imidazolium pendant structures, particularly tail length (n-butyl vs n-dodecyl). A physical model of electrode polarization is used to separate ionic conductivity of the ionomers into number density of conducting ions and their mobility. Tf2N- counterions display higher ionic conductivity and mobility than PF6- counterions, as anticipated by ab initio calculations. Ion mobility is coupled to polymer segmental motion, as these are observed to share the same Vogel temperature. Ionomers with the n-butyl tail impart much larger static dielectric constant than those with the n-dodecyl tail. From the analysis of the static dielectric constant using Onsager theory, there is more ionic aggregation in ionomers with the n-dodecyl tails than in those with the n-butyl tails, consistent with X-ray scattering, which shows a much stronger ionic aggregate peak for the ionomers with dodecyl tails on their imidazolium side chains.
- Choi, U Hyeok,Lee, Minjae,Wang, Sharon,Liu, Wenjuan,Winey, Karen I.,Gibson, Harry W.,Colby, Ralph H.
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- Synthesis of dicationic alkyl imidazolium peroxopolyoxotungsten-based phase transfer catalyst and its catalytic activity for olefin epoxidation
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Peroxopolyoxotungsten-based hybrid catalysts modified by dicationic long-chain alkyl imidazolium cations have been synthesized and characterized. The catalytic activity of the catalysts was measured for the epoxidation of olefins with H2O2. These catalysts proved to be high catalytic activity phase transfer catalysts. In particular, for the catalyst [D12min]1.5PW4O24 modified by the dodecyl dicationic imidazolium cation, the conversion of cyclohexene and selectivity for epoxycyclohexane were 97.7% and 96.3%, respectively. After the reaction, the catalyst could be recovered simply by filtration and reused four times. The conversion of cyclohexene and selectivity for epoxycyclohexane were still 72.4% and 97.2%, respectively, after recycling the catalyst four times. In addition, this phase transfer catalyst can be applied to the epoxidation of a wide range of olefins.
- Wu, Jianghao,Jiang, Pingping,Leng, Yan,Ye, Yuanyuan,Qin, Xiaojie
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- Synthesis of triethoxysilane imidazolium based ionic liquids and their application in the preparation of mesoporous ZSM-5
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Triethoxysilane containing imidazole based ionic liquids were synthesized. These ionic liquids were utilized as a structure directing agent for the synthesis of mesoporous ZSM-5. ZSM-5 was characterized by a complementary combination of X-ray diffraction, N2 adsorption/desorption, Scanning electron microscopy, Transmission electron microscopy, Temperature programmed desorption techniques, Infrared spectroscopy and Nuclear Magnetic Resonance spectroscopy. The resultant zeolites were mesoporous and showed unique characteristics of a fully crystalline microporous MFI zeolite framework. Mesoporous ZSM-5 synthesized from imidazole based ionic liquids exhibited higher catalytic activity than conventional ZSM-5 in alkylation and cracking reactions. Significantly high catalytic activity of the mesoporous ZSM-5 suggests that large external surface area and accessible acid sites are beneficial for catalytic reactions involving large organic molecules.
- Kore, Rajkumar,Srivastava, Rajendra
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- 1,2-Bis[N-(N′-alkylimidazolium)]ethane salts as new guests for crown ethers and cryptands
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1,2-Bis[N-(N′-alkylimidazolium)ethane salts form complexes presumed to be pseudorotaxanes with crown ether and cryptand hosts. The association constants of 1,2-bis[N-(N′-butylimidazolium)]ethane bis(hexafluorophosphate) with dibenzo-24-crown-8 and a dibenzo-24-crown-8-based pyridyl cryptand were estimated as 24 (±1) and 348 (±30) M -1, respectively, in acetonitrile at 25 °C. The pseudorotaxane-like structure of the 1:2 complex of the N′-methyl analog with the cryptand was observed by X-ray crystallography. Replacement of the ethylene spacer with propylene and butylene spacers resulted in Ka values an order of magnitude smaller.
- Lee, Minjae,Niu, Zhenbin,Schoonover, Daniel V.,Slebodnick, Carla,Gibson, Harry W.
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- The structure – Activity correlation in the family of dicationic imidazolium surfactants: Antimicrobial properties and cytotoxic effect
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Background: The development of new effective microbicide surfactants and the search for the structure–biological activity relationship is an important and promising problem. Surfactants containing imidazolium fragment attract attention of researchers in the field of chemotherapy, because these compounds often exhibit high antimicrobial activity. The aim of this work is to identify the newly synthesized surfactants from the viewpoint of their potential usefulness in pharmacology and medicine. For this purpose, a detailed study of antimicrobial, hemolytic and cytotoxic activity of dicationic alkylimidazolium surfactants of the m-s-m (Im) series with a variable length of a hydrocarbon tail (m = 10, 12) and a spacer fragment (s = 2, 3, 4) was carried out. Methods: Aggregation of surfactants in solutions was estimated by tensiometry and conductivity. Antimicrobial activity was determined by the serial dilution technique. Cytotoxic effects of the test compounds on human cancer and normal cells were estimated by means of the multifunctional Cytell Cell Imaging system. Cell Apoptosis Analysis was made by flow cytometry. Results: The test compounds show high antimicrobial activity against a wide range of test microorganisms and do not possess high hemolytic activity. Importantly, some of them display a bactericidal activity comparable to ciprofloxacin fluoroquinolone antibiotic against Gram-positive bacteria, including methicillin-resistant strains of S. aureus (MRSA). The cytotoxicity of the compounds against normal and tumor human cell lines has been tested as well, with cytotoxic effect and selectivity strongly controlled by structural factor and kind of cell line. Superior results were revealed for compound 10–4-10 (Im) in the case of HuTu 80 cell line (duodenal adenocarcinoma), for which IC50 value at the level of doxorubicin and a markedly higher selectivity index (SI 7.5) were demonstrated. Flow cytometry assay shows apoptosis-inducing effect of this compound on HuTu 80 cells, through significant changes in the potential of mitochondrial membrane. Major conclusions: Antibacterial properties are shown to be controlled by alkyl chain length, with the highest activity demonstrated by surfactants with decyl tail, with the length of the spacer fragment showing practically no effect. The results indicate that the mechanism of cytotoxic effect of the compounds can be associated with the induction of apoptosis via the mitochondrial pathway. General significance: Selectivity against pathogenic microorganisms and low toxicity against eukaryotic cells allow considering dicationic imidazolium surfactants as new effective antimicrobial agents. At the same time, high selectivity against some cancer cell lines indicates the prospect of their using as components of new anticancer drugs.
- Gumerova, Syumbelya K.,Kotenko, Alla A.,Kulik, Natalia V.,Mikhailov, Vasilii A.,Mirgorodskaya, Alla B.,Prokopyeva, Tatiana M.,Sapunova, Аnastasiia S.,Sinyashin, Oleg G.,Voloshina, Alexandra D.,Zakharova, Lucia Ya
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- Mono and co-immobilization of imidazolium ionic liquids on silica: Effects of the substituted groups on the adsorption behavior of 2,4-dinitrophenol
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Ionic liquid modified silicas with high adsorption capacity for phenols prompt us to deeply explore the contribution of interactions between the adsorbent and adsorbate, with a particular focus on hydrophobicity, π-π, electrostatic and acid-base interactions. Herein, by introducing a series of typical substituent groups including N,N-dimethylaminopropyl (A), benzyl (B), dodecyl (D) and naphthylmethyl (N) in an imidazole ring (Im), three mono-immobilized and two co-immobilized imidazolium ionic liquid modified silicas, namely SilprAImCl, SilprBImCl, SilprNImCl, SilprDBImCl and SilprDAImCl, werre synthesized for removal and recovery of 2,4-dinitrophenol (2,4-DNP) from aqueous solutions. Adsorption kinetics, isotherms, thermodynamic analysis and desorption experiments have been carried out. The experimental results reveal that the substituent groups such as N,N-dimethylaminopropyl, benzyl and naphthylmethyl on the imidazole ring can significantly enhance the adsorption of 2,4-DNP via the acid-base interaction or π-π interaction and the adsorption capacity of 2,4-DNP follows the order: SilprNImCl > SilprAImCl > SilprBImCl. Furthermore, SilprDBImCl exhibits the largest adsorption capacity and SilprDAImCl has the lowest among the five adsorbents. These interesting finds indicate that the combination of hydrophobicity and π-π interactions lead to enhanced adsorption performance towards 2,4-DNP, while the combination of the hydrophobicity and acid-base interactions can restrain greatly adsorption of 2,4-DNP from aqueous medium. Adsorption mechanisms of 2,4-DNP on the five adsorbents have been clarified. These results will provide a deeper insight for efficient removal of phenols from water environments.
- Wang, Zhike,Ge, Honglian,Wang, Xueyuan,Ye, Cunling,Fan, Shunli
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- Ruthenium complex immobilized on supported ionic-liquid-phase (SILP) for alkoxycarbonylation of olefins with CO2
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In this study, the heterogeneously catalyzed alkoxycarbonylation of olefins with CO2based on a supported ionic-liquid-phase (SILP) strategy is reported for the first time. An [Ru]@SILP catalyst was accessed by immobilization of ruthenium complex on a SILP, wherein imidazolium chloride was chemically integrated at the surface or in the channels of the silica gel support. An active Ru site was generated through reacting Ru3(CO)12with the decorated imidazolium chloride in a proper microenvironment. Different IL films, by varying the functionality of the side chain at the imidazolium cation, were found to strongly affect the porosity, active Ru sites, and CO2adsorption capacity of [Ru]@SILP, thereby considerably influencing its catalytic performance. The optimized [Ru]@SILP-A-2 displayed enhanced catalytic performance and prominent substrate selectivity compared to an independent homogeneous system under identical conditions. These findings provide the basis for a novel design concept for achieving both efficient and stable catalysts in the coupling of CO2with olefins.
- Xia, Shi-Ping,Ding, Guang-Rong,Zhang, Rui,Han, Li-Jun,Xu, Bao-Hua,Zhang, Suo-Jiang
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supporting information
p. 3073 - 3080
(2021/05/05)
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- Structure-activity relationship modeling and experimental validation of the imidazolium and pyridinium based ionic liquids as potential antibacterials of mdr acinetobacter baumannii and staphylococcus aureus
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Online Chemical Modeling Environment (OCHEM) was used for QSAR analysis of a set of ionic liquids (ILs) tested against multi-drug resistant (MDR) clinical isolate Acinetobacter baumannii and Staphylococcus aureus strains. The predictive accuracy of regression models has coefficient of determination q2 = 0.66 ? 0.79 with cross-validation and independent test sets. The models were used to screen a virtual chemical library of ILs, which was designed with targeted activity against MDR Acinetobacter baumannii and Staphylococcus aureus strains. Seven most promising ILs were selected, synthesized, and tested. Three ILs showed high activity against both these MDR clinical isolates.
- Semenyuta, Ivan V.,Trush, Maria M.,Kovalishyn, Vasyl V.,Rogalsky, Sergiy P.,Hodyna, Diana M.,Karpov, Pavel,Xia, Zhonghua,Tetko, Igor V.,Metelytsia, Larisa O.
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- A Remarkable Fluorescence Quenching Based Amplification in ATP Detection through Signal Transduction in Self-Assembled Multivalent Aggregates
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Signal transduction is essential for the survival of living organisms, because it allows them to respond to the changes in external environments. In artificial systems, signal transduction has been exploited for the highly sensitive detection of analytes. Herein, a remarkable signal transduction, upon ATP binding, in the multivalent fibrillar nanoaggregates of anthracene conjugated imidazolium receptors is reported. The aggregates of one particular amphiphilic receptor sensed ATP in high pm concentrations with one ATP molecule essentially quenching the emission of thousands of receptors. A cooperative merging of the multivalent binding and signal transduction led to this superquenching and translated to an outstanding enhancement of more than a millionfold in the sensitivity of ATP detection by the nanoaggregates; in comparison to the “molecular” imidazolium receptors. Furthermore, an exceptional selectivity to ATP over other nucleotides was demonstrated.
- Biswas, Rakesh,Naskar, Sumit,Ghosh, Surya,Das, Mousumi,Banerjee, Supratim
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supporting information
p. 13595 - 13600
(2020/10/06)
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- Gemini basic ionic liquid as bi-functional catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones at room temperature
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A cascade synthesis of 2,3-dihydroquinazolin-4(1H)-ones has been developed from 2-aminobenzonitriles and carbonyl analogues using Gemini basic ionic liquid as green catalyst cum solvent at room temperature. Both aldehydes and ketones were condensed with 2-aminobenzonitriles affording good to excellent yields of products. Moreover, the ionic liquids can be reused up to 5th cycle without significant loss of catalytic activity.
- Dutta, Apurba,Damarla, Krishnaiah,Kumar, Arvind,Saikia, Prakash J.,Sarma, Diganta
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supporting information
(2020/01/08)
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- Synthesis of Ionic Liquids as Novel Nanocatalysts for Fixation of Carbon Dioxide with Epoxides by Using a Carbon Dioxide Balloon
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Abstract: In the present study, the nanocatalyst of imidazolium based ionic liquids (ILs) is synthesized for the fixation of carbon dioxide (CO2) under moderate conditions by utilizing a balloon of CO2 with commercially available epoxides. IL incorporated porous dendritic fibrous nanosilica (DFNS) catalyst (IL/DFNS) was designed and synthesized. The synthesized catalyst was characterized using N2 absorption desorption isotherm, XPS, SEM, EDX, TGA, HR-TEM, and AFM. For cyclic carbonate, an environmental friendly catalyst of porous IL/DFNS indicate highly impressive catalytic efficiency from CO2 through CO2 fixation and epoxides under mild condition. Attendance of polar hydroxyl and anion exchange nature groups of IL frame work to high surface area is known as the main aspect to be reliable for elevated catalytic efficiency and also advance in stability of catalyst and providing a proper recyclability. Graphic Abstract: [Figure not available: see fulltext.].
- Zhang, Pu,Zhiani, Rahele
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p. 2254 - 2266
(2020/02/18)
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- Refining method for removing trace aldehyde group in 1,3-propylene glycol
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The invention relates to a method for removing residual trace aldehyde group-containing impurities in 1,3-propylene glycol (1,3-PDO). The method comprises: dehydrating and concentrating a 3-hydroxypropionaldehyde hydrogenation reaction product to obtain a 1,3-PDO solution containing trace aldehyde impurities, adding a sulfonic acid ionic liquid into the solution, carrying out aldehyde removal treatment at a certain temperature, carrying out reduced pressure rectification on the aldehyde-removed 1,3-PDO solution, and condensing the distillate to obtain the high-purity 1,3-PDO product. Accordingto invention, 1,3-PDO is produced by the acrolein hydration route; by using the method, the content of the residual aldehyde impurities can be reduced to less than 10 ppm, the product with a purity of higher than 99.7% is obtained, and the requirements of low-chrominance polyester PTT synthesis on the quality of raw materials are met; and the treatment method is simple to operate, and efficient,and the acidic ionic liquid can be recycled.
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Paragraph 0055
(2020/03/05)
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- Inhibition of bacterial growth and galactosyltransferase activity of WbwC by α, ω-bis(3-alkyl-1H-imidazolium)alkane salts: Effect of varying carbon content
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A series of compounds was designed and synthesized having two imidazolium rings separated by a polymethylene spacer and having alkyl substituents on each of the imidazolium rings. The compounds were assayed for their effects on the activity of galactosyltransferase WbwC, and also on the growth of Gram-negative and Gram-positive bacteria, as well as human cells. The inhibition observed on enzyme activities and cell growth was dependent on the total number of carbons in the spacer and the alkyl substituents on the imidazolium rings. These readily synthesized, achiral compounds have potential as antimicrobial and antiseptic agents.
- Brockhausen, Inka,Kocev, Alexander,Kong, Xianqi,Melamed, Jacob,Szarek, Walter A.,Vlahakis, Jason Z.,Wang, Shuo,Xu, Yaozu
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- N-Functionalised Imidazoles as Stabilisers for Metal Nanoparticles in Catalysis and Anion Binding
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Metal nanoparticles (NPs) have physicochemical properties which are distinct from both the bulk and molecular metal species, and provide opportunities in fields such as catalysis and sensing. NPs typically require protection of their surface to impede aggregation, but these coatings can also block access to the surface which would be required to take advantage of their unusual properties. Here, we show that alkyl imidazoles can stabilise Pd, Pt, Au, and Ag NPs, and delineate the limits of their synthesis. These ligands provide an intermediate level of surface protection, for which we demonstrate proof-of-principle in catalysis and anion binding.
- Beer, Paul D.,Cookson, James,Serpell, Christopher J.
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p. 683 - 690
(2020/07/03)
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- Photoisomerization and Mesophase Formation in Azo-Ionic Liquids
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Ionic liquids present a versatile, highly tunable class of soft functional materials. Aside from being low melting salts, they can be endowed with additional functionalities. In N-alkylimidazolium halides, which are a prominent class of ionic liquids (ILs), the imidazolium cation was linked via an ether-bridge to an azobenzene unit in order to obtain photoresponsive materials through photoinduced trans-cis isomerization. The azobenzene unit, in turn, was modified with electron-donating or -withdrawing groups such as methyl-, tert-butyl-, methoxy-, N,N-dimethylamino, and nitro groups to study their influence on the photoisomerization and phase behavior. Endowing the imidazolium additionally with a long alkyl chain allows the materials to potentially form liquid crystalline (LC) mesophases before melting into the isotropic liquid. All studied compounds qualify as ionic liquids, and all, except for the nitro-compound, show the formation of smectic mesophases melting to the isotropic liquid. The compounds with the bulkiest aliphatic substituent, the tert-butyl, shows the lowest melting point, the largest mesophase window, and an efficient photochemical trans-cis conversion (>90%). In summary, by tuning sterically and electronically the cationic part of ILs, a photoswitchable room temperature liquid crystal could be developed and design guidelines for photoresponsive ionic liquids could be obtained.
- Renier, Olivier,Bousrez, Guillaume,Stappert, Kathrin,Wilk-Kozubek, Magdalena,Adranno, Brando,Pei, Hanwen,Spielberg, Eike T.,Smetana, Volodymyr,Mudring, Anja-Verena
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p. 214 - 225
(2019/12/24)
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- Metal-free selective synthesis of 2-substituted benzimidazoles catalyzed by Br?nsted acidic ionic liquid: Convenient access to one-pot synthesis of N-alkylated 1,2-disubstituted benzimidazoles
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A novel efficient method for the selective synthesis of 2-substituted benzimidazoles is described through condensation reaction of o-phenylenediamines with a wide rang of aliphatic, aromatic and heteroaromatic aldehyde substrates using Br?nsted acidic ionic liquid as a reusable catalyst under metal-free conditions at ambient temperature. Notably, Dodecylimidazolium hydrogen sulfate ([DodecIm][HSO4]) is the most efficient catalyst for good to excellent yields of the corresponding products (up to 98%). Subsequently, this protocol was successfully applied for the preparation of N-alkylated 1,2-disubstituted benzimidazoles in high to excellent yields via sequential one-pot reaction. In addition, catalysts are recycled at least four times without significant loss in activity.
- Senapak, Warapong,Saeeng, Rungnapha,Jaratjaroonphong, Jaray,Promarak, Vinich,Sirion, Uthaiwan
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supporting information
p. 3543 - 3552
(2019/05/29)
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- Imidazole compounds containing biphenyl groups and preparation method thereof
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The invention belongs to the technical field of chemical materials and relates to imidazole compounds containing biphenyl groups and a preparation method thereof. The molecular formula of the productsis shown in the description, where R represents -(CH2)nCH3 and n is 0-13. N-methylimidazole-(N-dodecyl imidazole) and 4-(10-bromodecyloxy)-4-(dodecyloxy)biphenyl as raw materials undergo a microwavesynthesis reaction. The preparation and post-treatment method of the imidazole compounds are easy to operate and have small pollution on the environment. The imidazole compounds have liquid crystal structures through polarized light irradiation and have the good reversible phase change behavior in heating and cooling processes.
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Paragraph 0023; 0024
(2018/11/22)
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- Exploring the cellular uptake and localisation of phosphorescent rhenium: Fac -tricarbonyl metallosurfactants as a function of lipophilicity
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A systematic study of the cellular uptake of emissive complexes as a function of their lipophilicity is presented. Here a series of amphiphilic rhenium fac-tricarbonyl bisimine complexes bearing axial substituted imidazole or thiazole ligands, [Re(bpy)(CO)3(ImCnHm)]+ {n = 1 m = 3 (1+), n = 4 m = 9 (2+), n = 8 m = 17 (3+), n = 12 m = 25 (4+), n = 16 m = 33 (5+), n = 2 m = 3 (6+); bpy = 2,2′-bipyridine, Im = imidazole} and [Re(bpy)(CO)3(L)]+ {L = 1-mesitylimidazole, ImMes (7+), 4,5-dimethylthiazole, dmt (8+) and 4-methyl-5-thiazole-ethanol, mte (9+)} is reported. The X-ray crystal structures of 2+, 8+ and 9+ confirm the geometry and expected distribution of ligands and indicated that the plane of the imidazole/thiazole ring is approximately parallel to the long axis of the bipy ligand. Luminescence studies revealed excellent properties for their use in cell imaging with visible excitation and broad emission profiles. Their uptake in two distinct species has been examined by fluorescence imaging of the diplomonad fish parasite Spironucleus vortens (S. vortens) and rod-shaped yeast Schizosaccharomyces pombe (Schiz. pombe) as a function of their lipophilicity. The uptake of the complexes was highest for the more lipophilic 2+-5+ in both S. vortens and Schiz. pombe in which the long alkyl chain aids in crossing bilipid membranes. However, the increased lipophilicity of longer chains also resulted in greater toxicity. Localisation over the whole cell varied with differing alkyl chain lengths with complex 2+ preferentially locating to the nucleus of S. vortens, 3+ showing enhanced nuclear partitioning in Schiz. pombe, and 4+ for the remaining cell wall bound in the case of S. vortens. Interestingly, complexes of intermediate lipophilicity such as 7+ and 8+ showed reasonable uptake, proved to be non-toxic, and were capable of crossing exterior cell walls and localising in the organelles of the cells.
- Hallett, Andrew J.,Placet, Emeline,Prieux, Roxane,McCafferty, Danielle,Platts, James A.,Lloyd, David,Isaacs, Marc,Hayes, Anthony J.,Coles, Simon J.,Pitak, Mateusz B.,Marchant, Sarah,Marriott, Stephen N.,Allemann, Rudolf K.,Dervisi, Athanasia,Fallis, Ian A.
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supporting information
p. 14241 - 14253
(2018/10/25)
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- Preparation and application of neutral C-H bond anion recognition receptor
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The invention discloses a novel compound capable of detecting and recognizing chloride ions, particularly relates to preparation and application of a neutral C-H bond anion recognition receptor, and belongs to the technical field of supramolecular chemistry molecular recognition. The structural formula of the receptor compound is as follows (as shown in the description). Through the pyrimidine receptor compound based on a neutral C-H bond, the anion recognition property can be greatly improved, and the pyrimidine receptor compound and the chloride ion can form a stable complex compound in the proportion of the pyrimidine receptor compound to the chloride ions being 1 to 1. The compound is good in selectivity, high in combining capacity and high in sensitivity, can be used for detecting and recognizing the chloride ions in biological samples or environmental samples, and has good application prospects.
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Paragraph 0016
(2017/02/17)
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- 1,1 the [...] -di-alkyl -3,3 the [...] -(2-phosphate ester -1,3-propyl) imidazole in the process for the preparation of salt compound
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The invention relates to a 1,1'-dialkyl-3,3'-(2-phosphate-1,3-propylidene)imidazolium compound and a preparation method thereof. The structural formula of the 1,1'-dialkyl-3,3'-(2-phosphate-1,3-propylidene)imidazolium compound is shown in the specification, wherein n is 6, 8, 10, 12 and 14, and the alkyl imidazole can be replaced with alkyl benzimidazole. The 1,1'-dialkyl-3,3'-(2-phosphate-1,3-propylidene)imidazolium is a amphoteric dimeric surfactant, and a concrete synthesis method comprises the following steps: synthesizing 1, 3-dichloro-2-propanol, synthesizing N-alkyl imidazole, synthesizing 1,1'-dialkyl-3,3'-(2-hydroxyl-1,3-propylidene)imidazole hydrochloride, and synthesizing 1,1'-dialkyl-3,3'-(2-phosphate-1,3-propylidene)imidazolium. The 1,1'-dialkyl-3,3'-(2-phosphate-1,3-propylidene)imidazolium compound and the preparation method are easily available in raw materials, the reaction technology conditions are easy to control, operation is simple, the product is easy to purify, and yield is high. The compound has low critical micelle concentration, and can be used as a wetting agent, an emulsifier, a foaming agent and a foam stabilizer. A molecular structure has macrocyclic cefpimizole group and phosphate ester, and thus the compound has good thermal stability, solubility, salinity resistance, temperature resistance and acid and base resistance.
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Paragraph 0059; 0060
(2016/12/07)
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- Synthesis of surface-active N-heterocyclic carbene ligand and its Pd-catalyzed aqueous Mizoroki–Heck reaction
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A surface-active N-heterocyclic carbene (NHC) ligand with an octaethylene glycol monomethyl ether and n-dodecyl chain was synthesized. The NHC and its Pd complex behaved as a general surfactant, and hydrophobic oily substrates such as iodobenzene and styrene were emulsified in water, resulting in the acceleration of the Mizoroki–Heck reaction under heterogeneous conditions. Our results demonstrated that the reactive emulsion interface rendered by the surface-active NHC is effective for the aqueous Mizoroki–Heck reaction.
- Taira, Toshiaki,Yanagimoto, Takaya,Sakai, Kenichi,Sakai, Hideki,Endo, Akira,Imura, Tomohiro
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p. 4117 - 4122
(2016/07/06)
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- Complex compound
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PROBLEM TO BE SOLVED: To provide a new complex compound that can be used as a catalyst for an organic synthesis reaction and in particular a surfactant type catalyst having both functions of catalytic ability and surface active ability. SOLUTION: A complex compound comprises a nitrogen-containing heterocyclic carbene ligand represented by formula (A) and including at least one metal atom selected from palladium, silver, rhodium, iridium, and ruthenium as a central metal. (R1 represents a divalent hydrocarbon group that has 2-20 carbon atoms and may include at least one atom selected from N, O, S and halogen atoms; R2 represents a hydrocarbon group having 6-70 carbon atoms and including a polyoxyalkylene group and/or a polyglyceryl group having a polymerization number of 2-20 or a hydrocarbon group having 2-20 carbon atoms and including at least one ionic functional group selected from a sulfonic acid group, a carboxyl group, an ammonium group, or their salts; and R3 represents a hydrocarbon group having 2-20 carbon atoms) SELECTED DRAWING: None COPYRIGHT: (C)2016,JPO&INPIT
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Paragraph 0035
(2016/10/10)
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- Catalytic asymmetric cycloaddition of CO2 to epoxides via chiral bifunctional ionic liquids
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A series of new chiral ionic liquid catalysts composed of the N,N'-bis(salicyclidene) cyclohexene diaminatocobalt and an imidazolium salt were designed, prepared and applied for the chiral cyclic carbonate synthesis from racemic epoxides and carbon dioxide. All reactions exhibit good enantioselectivity for the chiral cyclic carbonate without polycarbonate and other by-products. The order of The order of catalytic activity toward the axial anions is OAc- > CF3CO2- > CCl3CO2- > OTs- and the order of enantioselectivity is OTs- > OAc- > CCl3CO2- > CF3CO2-.
- Duan, Shuhui,Jing, Xinyao,Li, Dandan,Jing, Huanwang
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- A Comprehensive Study on the Synthesis and Micellization of Disymmetric Gemini Imidazolium Surfactants
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Two groups of disymmetric Gemini imidazolium surfactants, [C14C4Cmim]Br2 (m?=?10, 12, 14) and [CmC4Cnim]Br2 (m?+?n?=?24, m?=?12, 14, 16, 18) surfactants, were synthesized and their structures were confirmed by 1H NMR and ESI–MS spectroscopy. Their adsorption at the air/water interface, thermodynamic parameters and aggregation behavior were explored by means of surface tension, electrical conductivity and steady-state fluorescence. A series of surface activity parameters, including cmc, γcmc, πcmc, pC20, cmc/C20, Γmax and Amin, were obtained from surface tension measurements. The results revealed that the overall hydrophobic chain length (Nc) for [C14C4Cmim]Br2 and the disymmetry (m/n) for [CmC4Cnim]Br2 had a significant effect on the surface activity. The cmc values decreased with an increase of Nc or m/n. The thermodynamic parameters of micellization (ΔGm θ, ΔHm θ, ΔSm θ) derived from the electrical conductivity indicated that the micellization process of [C14C4Cmim]Br2 and [CmC4Cnim]Br2 was entropy-driven at different temperatures, but the contribution of ΔHm θ to ΔGm θ was enhanced by increasing Nc or m/n. The micropolarity and micellar aggregation number (Nagg) were estimated by steady-state fluorescence measurements. The results showed that the surfactant with higher Nc or m/n can form larger micelles, due to a tighter micellar structure.
- Zhao, Xiaohui,An, Dong,Ye, Zhiwen
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p. 681 - 691
(2016/07/06)
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- Bronsted acidic ionic liquid [C3SO3HDoim]HSO4 catalyzed one-pot three-component Biginelli-type reaction: An efficient and solvent-free synthesis of pyrimidinone derivatives and its mechanistic study
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A series of Bronsted acidic ionic liquids (ILs) were prepared and used for Biginelli-type condensation reaction among aromatic aldehydes, urea or thiourea and cyclopentanone. Through this reaction, the synthesis of various pyrimidinones could be achieved. Of interest, it was found that the reaction was efficiently catalyzed by a novel, eco-friendly functionalized IL [C3SO3HDoim]HSO4, which could be reused for at least 7 times without significantly loss of catalytic activity. The reaction proceeded efficiently at 80 °C to afford the desired products in good yield (up to 96%). In addition, a possible mechanism that accounted for the IL [C3SO3HDoim]HSO4-catalyzed reaction was proposed.
- Zhou, Zhi-Lei,Wang, Peng-Cheng,Lu, Ming
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p. 226 - 230
(2018/03/27)
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- Alkyl-imidazolium glycosides: Non-ionic - Cationic hybrid surfactants from renewable resources
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A series of surfactants combining carbohydrate and imidazolium head groups were prepared and investigated on their assembly behavior. The presence of the imidazolium group dominated the interactions of the surfactants, leading to high CMCs and large molecular surface areas, reflected in curved rather than lamellar surfactant assemblies. The carbohydrate, on the other hand, stabilized molecular assemblies slightly and reduced the surface tension of surfactant solutions considerably. A comparative emulsion study discourages the use of pure alkyl imidazolium glycosides owing to reduced assembly stabilities compared with APGs. However, the surfactants are believed to have potential as component in carbohydrate based surfactant mixtures.
- Salman, Abbas Abdulameer,Tabandeh, Mojtaba,Heidelberg, Thorsten,Hussen, Rusnah Syahila Duali,Ali, Hapipah Mohd
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supporting information
p. 28 - 33
(2015/05/27)
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- Tris-imidazolium and benzimidazolium ionic liquids: A new class of biodegradable surfactants
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Based on imidazolium and benzimidazolium, two series of novel tris-cationic ionic liquid surfactants containing ester groups were synthesized simply from readily available starting materials in high yields. Biodegradability and surfactants properties of the tris-imidazolium and tris-benzimidazolium ionic liquids were investigated. Some compounds showed assembly behaviour in the pure form (i.e. absence of solvent) and in the presence of polar or nonpolar solvents. These surfactants are effectively reducing the surface tension of water in the range of 28-31 mN m-1. Through using the 'Closed-Bottle Test' OECD 301D, the incorporation of alkyl or phenyl side chains with ester groups in the same molecule significantly improved the biodegradation compared to sodium n-dodecyl sulphate (SDS) as a reference. The aliphatic alkyl side chain, i.e., butyl, hexyl, octyl, decyl and dodecyl, in both imidazolium and benzimidazolium ionic liquids have marked increasing biodegradation and phase behaviour results compared to aromatic side-chains.
- Al-Mohammed, Nassir N.,Duali Hussen, Rusnah Syahila,Alias, Yatimah,Abdullah, Zanariah
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p. 2869 - 2881
(2015/02/02)
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- Synthesis of polyoxymethylene dimethyl ethers from methylal and trioxane catalyzed by Br?nsted acid ionic liquids with different alkyl groups
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Br?nsted acid ionic liquids with different alkyl group carbon chain lengths and an alkane sulfonic acid group were synthesized through bromoalkane, imidazole and 1,4-butane sultone as raw materials. The structures and properties of the ionic liquids were experimentally characterized. Catalytic reaction of methylal (DMM) with trioxane (TOX) for preparation of polyoxymethylene dimethyl ethers (PODMEn, CH3O(CH2O)nCH3, where n > 1) was investigated in various Br?nsted acid ionic liquids with different carbon chain length of alkyl groups. The carbon chain length of alkyl groups and activity correlation for the ionic liquids was studied. It was found that the structures of ionic liquids were consistent with the designed structure and their purities were high. They possessed high thermal stability and wide liquid range. The hydrophobicity of ionic liquids became stronger with the increase of carbon chain length. With increasing the carbon chain length of ionic liquids, the selectivity of PODME3-8 is increased at first and then decreased. Among all the ionic liquids, [C6ImBS][HSO4] shows the best catalytic performance and the selectivity of PODME3-8 is 57.85%.
- Wu, Qin,Li, Weijiao,Wang, Min,Hao, Yu,Chu, Tonghua,Shang, Jiqing,Li, Hansheng,Zhao, Yun,Jiao, Qingze
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p. 57968 - 57974
(2015/07/20)
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- Temperature-responsive proton-conductive liquid crystals formed by the self-assembly of zwitterionic ionic liquids
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In the present study, we synthesized a series of ionic liquids by mixing amphiphilic imidazolium-type zwitterions with sulfonic acids containing different substituent groups. Nanostructured proton conductors having hexagonal and cubic structures were constructed by the self-assembly of these zwitterionic ionic liquids. These nanostructured proton conductors exhibited an assembled-structure dependent proton conduction behavior. The introduction of highly ordered liquid crystal structures efficiently improved ionic conductivity, suggesting the induction of proton conduction through a hopping mechanism. Temperature-responsive ionic conductivity behavior based on phase transition within the self-assembled liquid crystal structures was also observed.
- Gao, Xinpei,Lu, Fei,Dong, Bin,Zhou, Tao,Liu, Yizhi,Zheng, Liqiang
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p. 63732 - 63737
(2015/08/11)
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- Imidazolium-based zwitterionic surfactants: Characterization of normal and reverse micelles and stabilization of nanoparticles
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This paper presents the physicochemical properties of micellar aggregates formed from a series of zwitterionic surfactants of the type 3-(1-alkyl-3-imidazolio)propane-sulfonate (ImS3-n), with n = 10, 12, 14, and 16. The ImS3-n dipolar ionic surfactants represent a versatile class of dipolar ionic compounds, which form normal and reverse micelles. Furthermore, they are able to stabilize nanoparticles in water and in organic media. Aqueous solubility is too low at room temperature to allow characterization of micellar aggregates but increases with addition of salts, allowing determination of aggregation number and cmc. As expected, these parameters depend on the length of the alkyl chain, and cmc values follow Klevens equation. In the presence of NaClO4, all ImS3-n micelles become anionoid by incorporating ClO4- on the micellar interface. A special feature of these surfactants is the ability to form reverse micelles and solubilize copious amounts of saline solutions in chloroform. 1H NMR and infrared spectroscopic evidence showed that the maximum water to surfactant molar ratio w0 achievable depends on the concentration and type of salt dissolved. Reverse micelles of the ImS3-n surfactants can be used to stabilize metallic nanoparticles, whose size may be tuned by the amount of water dissolved.
- Souza, Franciane D.,Souza, Bruno S.,Tondo, Daniel W.,Leopoldino, Elder C.,Fiedler, Haidi D.,Nome, Faruk
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p. 3587 - 3595
(2015/04/14)
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- Tetrakis-imidazolium and benzimidazolium ionic liquids: A new class of biodegradable surfactants
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Novel series of tetra-cationic ionic liquids containing alkyl or phenyl side chains and ester groups within the same molecule were successfully prepared. Based on imidazolium and benzimidazolium, these ionic liquids were synthesized from readily available starting materials in high yield. Surfactant properties including liquid crystalline behaviour and surface properties as well as their biodegradability were investigated. Tetrakis-imidazolium ionic liquid compounds showed assembly behaviour in the pure form (i.e. spontaneously) and in the presence of polar or nonpolar solvents, while both imidazolium and benzimidazolium ionic liquids effectively reduced the surface tension of water in the range of 29-34 mN m-1. The incorporation of tetra alkyl or phenyl side chains into imidazolium and benzimidazolium ionic liquids with tetra-ester groups, significantly improved the biodegradation. 'Closed-Bottle Test' OECD 301D and sodium n-dodecyl sulphate (SDS) as a reference were used for evaluation. The linear alkyl side chains (i.e. butyl, hexyl, octyl, decyl and dodecyl) in both tetrakis-imidazolium and benzimidazolium ionic liquids promote the increasing in biodegradation and phase behaviour results comparing to aromatic side-chains.
- Al-Mohammed, Nassir N.,Duali Hussen, Rusnah Syahila,Ali, Tammar Hussein,Alias, Yatimah,Abdullah, Zanariah
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p. 21865 - 21876
(2015/11/27)
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- Synthesis of methylal from methanol and formaldehyde catalyzed by Br?nsted acid ionic liquids with different alkyl groups
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The catalytic reaction of methanol with formaldehyde for the preparation of methylal was investigated in various Br?nsted acid ionic liquids with different carbon chain length of alkyl groups. The structures, acidities, and properties of ionic liquids were experimentally characterized and theoretically analyzed. The Br?nsted acidity-viscosity-activity correlation for the ionic liquids was studied. Among all these ionic liquids, [C6ImBS][HSO4] exhibited the best catalytic performance, which was ascribed to its strong Br?nsted acidity and low viscosity. The catalytic activity of the ionic liquid was near that of concentrated sulfuric acid. The influences of ionic liquid dosage, reaction temperature and molar ratio of methanol to formaldehyde were explored using [C6ImBS]HSO4 as the catalyst. Under the optimal conditions of n(methanol):n(formaldehyde):n(ILs) = 2.5:1:0.0258, 60 °C, and 4 h, the conversion of formaldehyde can reach 63.37%. The ionic liquid [C6ImBS]HSO4 could be reused.
- Sun, Jiahan,Li, Hansheng,Song, Haoran,Wu, Qin,Zhao, Yun,Jiao, Qingze
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p. 87200 - 87205
(2015/11/09)
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- Imidazolium-functionalized β-cyclodextrin as a highly recyclable multifunctional ligand in water
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We describe here the synthesis and the catalytic properties of a novel dodecyl-imidazolium modified β-cyclodextrin as a self-assembled catalytic system (Fig. 1) in neat water for an effective Suzuki-Miyaura reaction. The introduction of the dodecyl-imidazolium motif on the primary face of the β-cyclodextrin allowed the development of a green highly recyclable catalytic system for reactions in an aqueous environment. We present the application of this system to the Suzuki-Miyaura coupling without the use of a co-solvent or stabilizing phosphine ligands in aqueous media. The catalytic system is highly recyclable, allowing the reuse of the palladium catalyst in subsequent catalytic runs without loss of activity. This journal is the Partner Organisations 2014.
- Kairouz, Vanessa,Schmitzer, Andreea R.
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supporting information
p. 3117 - 3124
(2014/06/10)
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- Antimicrobial activity and SAR study of new gemini imidazolium-based chlorides
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A series of 70 new 3,3′(α,ω-dioxaalkyl)bis(1- alkylimidazolium) chlorides were synthesized. They were characterized with respect to surface active properties and antimicrobial activity against the following pathogens: Staphylococcus aureus, Enterococcus faecalis, Acinetobacter baumannii, Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Pseudomonas aeruginosa, Candida krusei, and Candida albicans. In this article, besides description of the synthesis, we characterize a set of features of these compounds, concerning their structure (described by the length of the dioxaalkan spacer and the length of the alkyl substituent in the aromatic ring) and surface active properties (critical micelle concentration, value of surface tension at critical micelle concentration, value of surface excess, molecular area of a single particle, and free energy of adsorption of molecule). Then, we present a SAR study for Staphylococcus aureus, as one of the most widespread pathogenic strains, conducted with the help of the Dominance-based Rough Set Approach (DRSA), that involves identification of relevant features and relevant combinations of features being in strong relationship with a high antimicrobial activity of the compounds. The SAR study shows, moreover, that the antimicrobial activity is dependent on the type of substituents and their position at the chloride moiety, as well as on the surface active properties of the compounds.
- Pa?kowski, ?ukasz,B?aszczyński, Jerzy,Skrzypczak, Andrzej,B?aszczak, Jan,Kozakowska, Karolina,Wróblewska, Joanna,Kozuszko, Sylwia,Gospodarek, Eugenia,Krysiński, Jerzy,S?owiński, Roman
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p. 278 - 288
(2014/03/21)
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- Peroxopolyoxotungsten-based ionic hybrid as a highly efficient recyclable catalyst for epoxidation of vegetable oil with H2O2
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A peroxopolyoxotungsten-based ionic hybrid was synthesized by anion-change of peroxopolyoxometalate (POM) PW4O243- with dicationic long-chain alkyl imidazolium ionic liquids. The characterization was conducted by FT-IR, TGA, 1H-NMR and CHN Elemental analyses. Its catalytic performance was evaluated by the epoxidation of soybean oil with H2O2 under solvent-free condition, including testing of organic cations influence, catalytic reusability and reaction conditions. The catalyst was proved to be a highly efficient recyclable catalyst for epoxidation of various vegetable oils with H2O2, showing high H 2O2 utilization efficiency, high catalytic activity, convenient recovery and good reuse ability.
- Wu, Jianghao,Jiang, Pingping,Qin, Xiaojie,Ye, Yuanyuan,Leng, Yan
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p. 1675 - 1680
(2014/07/07)
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- CO2/N2 triggered Switchable surfactants with imidazole group
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In order to overcome the hydrolysis of 2-alkyl-1-hydroxyethyl imidazoline and its unsatisfactory emulsification-demulsification switchability to water-alkane, the long-chain N-alkylimidazole compounds were synthesized by n-octyl bromide, n-decyl bromide, n-dodecyl bromide, n-tetradecyl bromide and n-hexadecyl bromide with imidazole, respectively and characterized by MS, 1H NMR and FTIR. The long-chain N-alkylimidazole compounds can be reversibly transformed into charged surfactants by exposure to CO2. Surface tension values indicated that N-alkylimidazolium bicarbonates had excellent surface activity compared with corresponding conventional surfactants with a lower γ CMC. The surface behaviors of the five surfactants can be illustrated by A min. Five conductivity cycles by bubbling CO2 and N2 alternately indicated that these surfactants could be switched by CO2 reversibly and repeatedly. Emulsions were repeatedly stabilized for five cycles by N-alkylimidazolium bicarbonate and broken by bubbling N2 through the solutions to reverses the reaction, releasing CO2.
- Chai, Mingfeng,Zheng, Zhibo,Bao, Lei,Qiao, Weihong
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p. 383 - 390
(2014/05/20)
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- Hyperbranched polymeric ionic liquids with onion-like topology as transporters and compartmentalized systems
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A new family of hyperbranched polymeric ionic liquids ("hyperILs" ) with onion-like topology and facile polarity design were tailored as transporters and compartmentalized systems. Applications include transport and dispersion of water-soluble dyes and functionalized graphene nanosheets from aqueous phase into nonpolar fluids, including polymer melts.
- Schueler, Fabian,Kerscher, Benjamin,Beckert, Fabian,Thomann, Ralf,Muelhaupt, Rolf
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supporting information
p. 455 - 458
(2013/02/26)
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- Chemo-immunotherapeutic antimalarials targeting isoprenoid biosynthesis
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We synthesized 30 lipophilic bisphosphonates and tested them in malaria parasite killing (targeting parasite geranylgeranyl diphosphate synthase, GGPPS) and human γδ T cell activation (targeting human farnesyl diphosphate synthase, FPPS). Similar patterns of activity were seen in inhibiting human FPPS and Plasmodium GGPPS, with short to medium chain-length species having most activity. In cells, shorter chain-length species had low activity, due to poor membrane permeability, and longer chain length species were poor enzyme inhibitors. Optimal activity was thus seen with ～C 10 side-chains, which have the best combination of enzyme inhibition and cell penetration. We also solved the crystal structure of one potent inhibitor, bound to FPPS. The results are of interest since they suggest the possibility of a combined chemo/immuno-therapeutic approach to antimalarial development in which both direct parasite killing and γδ T cell activation can be achieved with a single compound.
- Zhang, Yonghui,Zhu, Wei,Liu, Yi-Liang,Wang, Hong,Wang, Ke,Li, Kai,No, Joo Hwan,Ayong, Lawrence,Gulati, Anmol,Pang, Ran,Freitas-Junior, Lucio,Morita, Craig T.,Oldfield, Eric
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supporting information
p. 423 - 427
(2013/06/05)
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- Symmetrical 1, 3-Dialkylimidazolium Based Ionic Liquid Crystals
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The synthesis and characterization for a series of symmetrical 1, 3-dialkylimidazolium salts with different chain lengths and counter anions together with their 1-alkylimidazole precursors are described. Liquid crystal (LC) properties of these salts are studied. Images under polarizing optical microscopy show focal conic texture together with homeotropic domains. A smectic A mesophase, typical for rod-like imida-zolium salts, is assigned. Studies from powder X-ray diffraction suggest a lamellar structure with non-interdigitated monolayer arrangement for the LC salts in the mesophase. In addition, a short note on the structure and property relationship for rod-like, discor fan-like, and dendritic shaped imidazolium ionic liquid crystals (ImILCs) forming smectic, columnar, and cubic phase is briefly summarized. Acomparison of minimum alkyl chain length needed for 1-alkyl-3-methyl and symmetrical 1, 3-dialkyl ImILCs to exhibit LC behavior is addressed.
- Rohini, Rondla,Lee, Ching-Kuan,Lu, Jung-Tang,Lin, Ivan J.B.
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p. 745 - 754
(2013/11/06)
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- Anisotropic ionic conductivity in fluorinated ionic liquid crystals suitable for optoelectronic applications
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In this work, we report a library of thirteen fluorinated ionic liquids consisting of iodide salts of 1-alkyl-3-polyfluoroalkyl-imidazolium cations. By changing the length of the alkyl and polyfluoroalkyl pendants, we discovered that particular combinations of these result in compounds showing a mesophase. The nature and the molecular arrangement of the mesophase are characterised by polarised optical microscopy and powder X-ray diffraction analysis, among others. We demonstrate that, after the addition of I2 to generate the I-/I3- redox couple, anisotropic ionic conductivity takes place along preferential pathways in the lamellar structure of the mesophase. Notably, the addition of I2 does not suppress the mesophase temperature range, contrary to previously reported systems. Furthermore, the tendency of these materials to supercool allows the molecular arrangement in the mesophase to be retained in a solid film at ambient temperatures. Finally, we demonstrate their applicability as a quasi-solid electrolyte by preparing dye-sensitised solar cells with power conversion efficiencies comparable to the previous reports.
- Abate, Antonio,Petrozza, Annamaria,Cavallo, Gabriella,Lanzani, Guglielmo,Matteucci, Francesco,Bruce, Duncan W.,Houbenov, Nikolay,Metrangolo, Pierangelo,Resnati, Giuseppe
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p. 6572 - 6578
(2013/07/26)
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- Isoprene as lithiation mediator: Synthesis of 2-substituted 1-alkylimidazole derivatives
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The lithiation of different imidazoles bearing a primary (i.e., butyl, pentyl, dodecyl) or secondary (i.e., cyclohexyl, 1-methylheptyl) alkyl substituent on the nitrogen has been successfully achieved by means of an isoprene-mediated protocol. The subsequent reaction of the 2-lithioimidazole intermediates with different electrophiles leads to the formation of interesting 1,2-disubstituted imidazoles. Georg Thieme Verlag Stuttgart · New York.
- Martinez, Regina,Torregrosa, Rosario,Pastor, Isidro M.,Yus, Miguel
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experimental part
p. 2630 - 2638
(2012/09/07)
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- 1,2-Bis[N-(N′-alkylimidazolium)]ethane salts: A new class of organic ionic plastic crystals
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A new class of organic ionic plastic crystals was discovered. A series of alkylene 1,2-bis[N-(N′-alkylimidazolium)] salts with Br- and PF6- anions was prepared and most of the ethylene (C 2) linked compounds undergo multiple solid-solid phase transitions as determined by differential scanning calorimetry (DSC). The salts with longer spacers (C3 or C4) between the imidazolium units do not display any solid-solid transitions. The PF6- salts with terminal C10 and C12n-alkyl moieties are "classical" organic ionic plastic crystals by Timmermans' definition; they have low ΔSf (11 J K-1 mol-1 for C10 and 12 J K-1 mol-1 for C12). Additionally, the C2 linked bis-imidazolium salts with n-butyl, n-hexyl, n-heptyl and n-octyl termini all undergo two, three or four solid state transitions and exhibit ΔSf values in the range of 36-49 J K-1 mol-1, which are similar to those of other known ionic plastic crystalline materials. These materials were additionally characterized via ionic conductivity and solid state NMR. These ionic plastic crystals are presumably single-ion conductors, but the ionic conductivities appear to be too low for practical applications. The activation energy for conduction decreases as these compounds are heated through each solid-solid transition. The lack of any change in solid state 2H NMR spectra with temperature indicates that there is no change in phenyl ring flipping, suggesting no change in the imidazolium local environment. A resolution of this apparent dichotomy is perhaps that the counterions reside with the ethylene spacers between imidazolium moieties.
- Lee, Minjae,Choi, U Hyeok,Wi, Sungsool,Slebodnick, Carla,Colby, Ralph H.,Gibson, Harry W.
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supporting information; experimental part
p. 12280 - 12287
(2011/12/21)
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- Synthesis and self-aggregation of a hydroxyl-functionalized imidazolium-based ionic liquid surfactant in aqueous solution
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This paper deals with the synthesis and self-aggregation of a hydroxyl-functionalized imidazoliumbased ionic liquid (IL) surfactant, namely 1-hydroxyethyl-3-dodecylimidazolium chloride ([C2OHC 12im]Cl). The molecular structure was confirmed by means of electrospray ionization mass spectrometry (ESI-MS), 1H nuclear magnetic resonance (1H NMR) and elemental analysis. Many important physicochemical parameters, such as the critical micelle concentration (CMC), the surface tension at CMC (γCMC), the adsorption efficiency (pC20), the surface pressure at CMC (ΠCMC), the maximum surface excess (Γm), the minimum molecular cross-sectional area (Amin), the value of CMC/C20, the average number of aggregation (Nm) and the micellar microenvironment polarity were determined by surface tension-concentration curves, fluorescence spectra, and electrical conductivity. The phenomena of the second CMC, the concentration dependence of Nm, and the critical average aggregation number (N m,c) of imidazolium-based IL surfactants are reported for the first time in this paper. AOCS 2010.
- Liu, Xue-Feng,Dong, Li-Li,Fang, Yun
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experimental part
p. 203 - 210
(2012/04/17)
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- A Novel zwitterionic imidazolium-based ionic liquid surfactant: 1-carboxymethyl-3-dodecylimidazolium inner salt
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A novel zwitterionic imidazolium-based ionic liquid (IL) surfactant, 1-carboxymethyl-3-dodecylimidazolium inner salt, was synthesized. The molecule structure was confirmed by means of electrospray ionization mass spectrometry, 1H nuclear magnetic resonance and elemental analysis. The isoelectric point (pI) is 3.8 ± 0.1 at 35 ± 0.1 °C. The other important physicochemical parameters such as the critical micelle concentration (CMC), the surface tension at CMC (γCMC), the adsorption efficiency (pC 20), the surface pressure at CMC (ΠCMC), the maximum surface excess (Γm), the minimum molecular cross-sectional area (A min), the value of CMC/C 20 and the average number of aggregation (N m) were determined by surface tension and steady-state fluorescence probe methods, respectively. AOCS 2011.
- Liu, Xue-Feng,Dong, Li-Li,Fang, Yun
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experimental part
p. 497 - 504
(2012/07/28)
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- Structure and properties of N, N-alkylene bis(Na?2-alkylimidazolium) salts
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A series of N,N-alkylene bis(Na?2-alkylimidazolium) salts with various anions was prepared and characterized. The hydrogen-bonding abilities and ion-pairing strengths of the salts in solution were varied by changing the solvent and anion. Qualitatively, the extent of ion pairing of the 1,2-bis[N-(Na?2-butylimidazolium)]ethane salts with different anions was determined in acetone-d6 by 1H NMR spectroscopy. Thermal properties of the imidazolium salts were related not only to the nature of anions but also to the spacer length between imidazolium cations. Exceptionally high melting points of 1,2-bis[N-(Na?2-alkylimidazolium)]ethane bis(hexafluorophosphate)s can be explained by multiple hydrogen bonds observed in the X-ray crystal structures. Moreover, a trans conformation of the ethylene spacer of 1,2-bis[N-(Na?2-alkylimidazolium)]ethane bis(hexafluorophosphate)s allows good stacking structure in the crystals. ? 2010 American Chemical Society.
- Lee, Minjae,Niu, Zhenbin,Slebodnick, Carla,Gibson, Harry W.
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experimental part
p. 7312 - 7319
(2010/10/01)
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- Peroxopolyoxometalate-based room temperature ionic liquid as a self-separation catalyst for epoxidation of olefins
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A new peroxopolyoxometalate-based room temperature ionic liquid (POM-RTIL) has been synthesized and used as catalyst for efficient epoxidation of various olefins. The RTIL catalyst was found to be well dissolved in the solvent (ethyl acetate) during the reaction, while it can self-separate from the reaction media at room temperature after the reaction completed, which made the recovery and reuse of the IL catalyst convenient. The POM-RTIL catalyst can be recycled for five times without significant loss of activity.
- Li, Huan,Hou, Zhenshan,Qiao, Yunxiang,Feng, Bo,Hu, Yu,Wang, Xiangrui,Zhao, Xiuge
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scheme or table
p. 470 - 475
(2010/11/21)
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- Morita-baylis-hillman reaction on water without organic solvent, assisted by a 'catalytic' amount of amphiphilic imidazole derivatives
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A Morita-Baylis-Hillman (MBH) reaction using water as a solvent without any organic solvent can be performed by using an amphiphilic N-alkylimidazole. This reaction is accelerated by the addition of water and is the first example of a 'catalytic' MBH reaction without organic solvent in the presence of water.
- Asano, Keisuke,Matsubara, Seijiro
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experimental part
p. 3219 - 3226
(2010/02/28)
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