- 1-Alkenyl-3-methylimidazolium trifluoromethanesulfonate ionic liquids: Novel and low-viscosity ionic liquid electrolytes for dye-sensitized solar cells
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Dye-sensitized Solar Cells (DSCs) based on ruthenium complex N719 as sensitizer have received much attention due to their affordability and high efficiency. However, their best performance is only achieved when using volatile organic solvents as electrolyte solutions, which are unstable under prolonged thermal stress. Thus, we developed a new series of 1-alkenyl-3-methylimidazolium trifluoromethanesulfonate ionic liquids used as robust DSC electrolytes. These ionic liquids exhibit low viscosity, high conductivity, and thermal stability. The implementation of 1-but-3-enyl-3-methyl-imidazolium trifluoromethanesulfonate, [ButMIm]OTf, into DSCs gave the best photovoltaic performance. The results are fairly comparable to those reports for other popular ionic liquid electrolytes currently used in DSC field. An insightful discussion on the relationship between the structure of these new ionic liquids and the J-V characterization as well as electrochemical impedance measurement of DSCs will give more interesting information. The results are useful for large-scale outdoor application of DSCs.
- Nguyen, Phuong Tuyet,Nguyen, Trang Ngoc,Nguyen, Vinh Son,Nguyen, Hai Truong,Thi Ngo, Dung Kim,Tran, Phuong Hoang
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- Synthesis and thermophysical characterization of novel azide functionalized imidazolium based ionic liquids
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Several new monocationic and unsymmetrical dicationic azide functionalized ionic liquids (ILs) were synthesized. FT-IR, 1H NMR, 13C NMR and elemental analyses were applied to identify the molecular structure of these compounds. The density of these ionic liquids was measured too. Unsymmetrical dicationic ionic liquids had higher density than monocationic analogues. The shear viscosity of a dicationic ionic liquid ((1-(2-azido-3-methyl-3H-imidazole-1-ium) propyl)-3-vinyl-3H-imidazole-1-ium di-dicyanamide) and its corresponding monocationic analogue were also measured. Further thermal behaviour and heat capacity of this dicationic ionic liquid were investigated by TGA and DSC techniques. TGA analysis suggested that the decomposition temperature increases with increasing the heating rate and unsymmetrical dicationic ionic liquid has good thermal stability (up to 502.4-533.6 K) and heat capacity (298-343 K).
- Fareghi-Alamdari, Reza,Hatefipour, Razieh
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- Allylimidazolium halides as novel room temperature ionic liquids
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Liquid state halide salts composed of imidazolium cations having allyl groups were prepared. Their ionic conductivity, viscosity, and thermal properties were investigated. Introduction of allyl group on N-position effectively suppressed the crystallizatio
- Mizumo, Tomonobu,Marwanta, Edy,Matsumi, Noriyoshi,Ohno, Hiroyuki
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Read Online
- Quantum dots in which ionic liquids are ion-bonded and their preparation method
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A quantum dot particle in which an ionic liquid is ion-bonded is disclosed. The quantum dot particle includes a quantum dot having a core/shell nanostructure; and an ionic liquid compound represented by following Chemical Formula 1, bonded to the surface of the quantum dot, wherein the quantum dot and the ionic liquid compound form an ionic bond: wherein, R1 and R2 are each independently a branched or unbranched hydrocarbon group having 1 to 22 carbon atoms, and X? is a monovalent anion, wherein the hydrocarbon group includes a saturated or unsaturated group and may include one or more hetero atoms.
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Page/Page column 17
(2021/09/01)
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- Dimethyldioxirane (DMDO) as a valuable oxidant for the synthesis of polyfunctional aromatic imidazolium monomers bearing epoxides
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Conventional organic salts represent a new paradigm in many areas of research. Despite their great potential, an improvement in their physicochemical properties requires the chemical modification of their intrinsic structure. Thus, an efficient pathway was developed for the preparation of polyfunctional imidazolium monomers incorporating aromatic rings and terminal epoxides which presented a real synthetic challenge. In this work, we describe the reactivity of various oxidizing agents to develop a strong, clean and powerful methodology to generate epoxidized salts. Various reaction conditions for the formation of the epoxides were investigated such as the role of the cation and the counterion as well as the influence of an aromatic and/or aliphatic linker chain. Finally, we have evaluated the thermal properties of these new polyfunctional salts by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC).
- Chardin,Rouden,Livi,Baudoux
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supporting information
p. 5054 - 5059
(2017/11/09)
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- Low viscosity azide-containing mono and dicationic ionic liquids with unsaturated side chain
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A new class of azide-functionalized monocationic and unsymmetrical dicationic ionic liquids (ILs) with low viscosity and high liquid range was synthesized. All of the synthesized ILs, were characterized by FT-IR, 1HNMR, 13CNMR spectroscopies and elemental analysis. Some thermophysical properties including melting point, density, shear viscosity, decomposition temperature and heat capacity of the unsymmetrical dicationic azide functionalized IL with dicyanamide (DCA) were measured. To find the unique and general features of this dicationic IL, its properties were compared with the ones of the similar monocationic ILs. The results showed that the shear viscosity, density, thermal stability and heat capacity of the unsymmetrical dicationic IL are higher than monocationic analogues. In addition we found that the shear viscosity for the synthesized unsymmetrical dicationic IL containing azide group and DCA anion is 83.9?cP whereas the shear viscosities for other dicationic ILs reported in the literature are higher than 240?cP.
- Fareghi-Alamdari, Reza,Hatefipour, Razieh
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p. 793 - 799
(2016/12/30)
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- Ion-Tagged Oligonucleotides Coupled with a Magnetic Liquid Support for the Sequence-Specific Capture of DNA
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The isolation of specific nucleic acid sequences is a major bottleneck in molecular diagnostics. Magnetic beads/particles are typically used as solid supports for the capture of DNA targets to improve sample throughput but aggregate over time resulting in lower capture efficiency and obstruction of liquid handling devices. Herein, we describe a particle-free approach to sequence-specific DNA extraction using a magnetic liquid support and ion-tagged oligonucleotide (ITO) probes. ITO conjugates were synthesized with the highest yields ever achieved for the radical thiol-ene coupling of a substrate and oligonucleotide. In addition to distinguishing nucleotide mismatches, the ITO and magnetic liquid-based approach was more sensitive than a commercial magnetic bead-based method for the capture of target DNA from a pool of interfering genomic DNA.
- Clark, Kevin D.,Varona, Marcelino,Anderson, Jared L.
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supporting information
p. 7630 - 7633
(2017/06/13)
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- Bifunctional hydrophobic ionic liquids: Facile synthesis by thiol-ene "click" chemistry
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We describe the facile, robust and orthogonal fabrication of a structurally comprehensive library of hydrophobic trimethoxysilyl-functionalized ionic liquids with C7-C15 thioether spacer, using thiol-ene "click" chemistry. The synthesized ionic liquids displayed very low glass transition temperatures, high thermal stability and were hydrophobic in character. And the ability to serve as surface coating agents was tested by immobilizing them on the surface of iron oxide supermagnetic nanoparticles and the organic loadings were quantified.
- Sanchez Zayas, Manuel,Gaitor, Jamie C.,Nestor, Stephen T.,Minkowicz, Samuel,Sheng, Yinghong,Mirjafari, Arsalan
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p. 2443 - 2452
(2016/05/19)
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- Synthesis and thermal characterization of mono and dicationic imidazolium pyridinium based ionic liquids
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A series of monocationic and dicationic ionic liquids, in which each ionic liquid is associated with dicyanamide anion, are synthesized. The molecular structures of these compounds were identified by 1H-NMR, FT-IR and CHN analysis. Thermal behaviors of these ionic liquids were also investigated by thermogravimetry (TGA). The results suggested that all new ionic liquids have reasonable thermal stabilities, however, dicationic ionic liquids show more thermal stability than monocationics.
- Alamdari, Reza Fareghi,Zamani, Faezeh Ghorbani,Shekarriz, Marzieh
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p. 1127 - 1132
(2015/10/28)
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- Functionalized Ionic Liquids and Their Applications
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Disclosure of functionalized ionic liquids. Use of disclosed ionic liquids as solvent for carbon dioxide. Use of disclosed ionic liquids as flame retardant. Use of disclosed ionic liquids for coating fabric to obtain flame retardant fabric.
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Paragraph 029; 0250
(2014/09/30)
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- Structural diversity of copper(I)-N-heterocyclic carbene complexes; Ligand tuning facilitates isolation of the first structurally characterised copper(I)-NHC containing a copper(I)-alkene interaction
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The preparation of a series of imidazolium salts bearing N-allyl substituents, and a range of substituents on the second nitrogen atom that have varying electronic and steric properties, is reported. The ligands have been coordinated to a copper(I) centre and the resulting copper(I)-NHC (NHC=N-heterocyclic carbene) complexes have been thoroughly examined, both in solution and in the solid-state. The solid-state structures are highly diverse and exhibit a range of unusual geometries and cuprophilic interactions. The first structurally characterised copper(I)-NHC complex containing a copper(I)-alkene interaction is reported. An N-pyridyl substituent, which forms a dative bond with the copper(I) centre, stabilises an interaction between the metal centre and the allyl substituent of a neighbouring ligand, to form a 1D coordination polymer. The stabilisation is attributed to the pyridyl substituent increasing the electron density at the copper(I) centre, and thus enhancing the metal(d)-to-alkene(π*) back-bonding. In addition, components other than charge transfer appear to have a role in copper(I)-alkene stabilisation because further increases in the Lewis basicity of the ligand disfavours copper(I)-alkene binding.
- Lake, Benjamin R. M.,Willans, Charlotte E.
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supporting information
p. 16780 - 16790
(2014/01/06)
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- Asymmetric rhodium-directed anti-markovnikov regioselective boracyclopentannulation
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A Shimoi-type activation of B-H bond of NHC-boranes by a diphosphane-ligated cationic Rh complex was applied in an unprecedented intramolecular hydroboration reaction of simple olefins. The use of NHC-boranes as hydroborating reagents is still undisclosed due to their nonreactivity toward alkenes which could be explained by the high stability of this complex rendering it unable to provide a "free" borane hydroborating reagent. B-H bond Rh activation of NHC-borane circumvents this limitation, and asymmetric Rh-directed anti-Markovnikov boracyclopentannulation reaction led to a library of enantioenriched cyclic boranes in high yield (up to 94%) with high regio- (up to 100%) and enantioselectivity (er up to 99.2:0.8). This new activation mode of NHC-boranes highlights their use in organometallic chemistry and offers a very good approach to access chiral cyclic NHC-boranes.
- Toure, Momar,Chuzel, Olivier,Parrain, Jean-Luc
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supporting information
p. 17892 - 17895
(2013/01/15)
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- Parallel microwave-assisted synthesis of ionic liquids and screening for denitrogenation of straight-run diesel feed by liquid-liquid extraction
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Fifty-six ionic liquids were efficiently synthesized in parallel format under one-pot, solvent-free microwaveassisted synthesis. These compounds were evaluated as extracting agents of nitrogen-containing compounds from a real Diesel feed before being submitted to the hydrodesulfurization process to obtain ultralow sulfur Diesel. Our results showed that halogenated ionic liquids are an excellent alternative due to these ionic liquids are relatively inexpensive, presenting a high selectivity for the extraction of nitrogen-containing compounds and can be regenerated and recycled.
- Ceron, Miguel A.,Guzman-Lucero, Diego J.,Palomeque, Jorge F.,Martinez-Palou, Rafael
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experimental part
p. 427 - 432
(2012/07/01)
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- A superior new route to methyl phosphonate-based ionic liquids
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In the search for new ionic liquids (ILs) for biomass processing, analytical chemistry, or modern nonvolatile fire retarding agents, alkyl phosphonate-based ILs represent very promising candidates. A very practical synthesis of such ILs, which is superior to the conventional quaternization of 1-alkylimidazoles by dimethyl phosphite (DMP), was developed. 1,3-Dialkylimidazolium halide salts serve as convenient starting materials, and various 1,3-dialkylimidazolium methyl phosphonates are thus accessible by simple, fast, and solventfree procedures with DMP, where the anion is methylated.
- Froschauer, Carmen,Laus, Gerhard,Schottenberger, Herwig,Weber, Hedda K.,Sixta, Herbert,Kahlenberg, Volker
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supporting information
p. 945 - 946,2
(2020/08/31)
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- Further investigation of the biodegradability of imidazolium ionic liquids
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In continuation of our earlier investigations, this report presents a rationale behind the design of a series of imidazolium based ionic liquids and their biodegradation using the CO2 headspace test (ISO 14593 method, OECD 310). The effect on biodegradability of these salts through variation of the N-substituted side chains of imidazolium ions was examined further through incorporation of various functional groups and increased alkyl chain lengths. A series of anions containing moieties known to be biodegradable were also incorporated into a number of imidazolium based salts and examined in a similar fashion.
- Harjani, Jitendra R.,Farrell, Jeff,Garcia, M. Teresa,Singer, Robert D.,Scammells, Peter J.
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experimental part
p. 821 - 829
(2010/04/23)
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- Thermodynamic properties of mixtures containing ionic liquids: Activity coefficients at infinite dilution of organic compounds in 1-propyl boronic acid-3-alkylimidazolium bromide and 1-propenyl-3-alkylimidazolium bromide using inverse gas chromatography
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Activity coefficients at infinite dilution γ∞ of 28 organic compounds in eight room-temperature ionic liquids of the family of 1-propyl boronic acid-3-alkylimidazolium bromide and 1-propenyl-3-alkylimidazolium bromide (with alkyl = methyl, octyl, decyl, or dodecyl) were determined at 323.15 K using inverse gas chromatography. Using all the available γ∞ data, the selectivities at infinite dilution S12 ∞ were determined. Indeed, such values are extremely useful for the design and the optimization of separation processes.
- Mutelet, Fabrice,Jaubert, Jean-Noel,Rogalski, Marek,Boukherissa, Malika,Dicko, Amadou
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p. 1274 - 1279
(2007/10/03)
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- IONIC LIQUIDS BASED ON IMIDAZOLIUM SALTS INCORPORATING A NITRILE FUNCTIONALITY
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Novel chemical compounds of the general formula K+A-, in which K+ is a 5- or 6- membered heterocyclic ring having 1-3 hetereo atoms, which can be independently N, S, or 0; with the proviso that at least one of the hetereo atoms must be a quaternized nitrogen atom having a -R'CN substituent, wherein R' is alkyl (C1 to C12); the heterocyclic ring having up to 4 or 5 substituents independently chosen from the moieties: (i) H; (ii) halogen or (iii) alkyl (C1 to C12) , which is unsubstituted or partially or fully substituted by further groups, preferably F, Cl, N(CnF(2n+1-x)Hx)2, O(CnF(2n+1-x)Hx), S02(CnF(2n+1-x)Hx)2 or CnF(2n+1-x)Hx where 1nF(2n+1-x.)Hx.)2, O(CnF(2n+1-x)Hx), S02(CnF(2n+1-x)Hx)2 or CnF(2n+1-x)Hx where 1- is any anion that provides a salt with a low melting point, below about 100 °C; A- can be halide, BF4- , PF6-, N03-, CH3CO2-, CF3SO3-, (CF3SO2)2N-, (CF3SO2)3C- CF3CO2- or N(CN)2- or [BF3RCN]-. These compounds can be used as industrial solvents, especially as ligands for efficient catalyst recycling.
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Page/Page column 18
(2008/06/13)
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- Syntheses of very dense halogenated liquids
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A family of halogenated liquids with densities ranging from 1.95 to 2.80 g cm-3 was readily synthesized by a one-pot procedure. These liquids exhibit characteristics of ionic liquids with melting/transition points lower than room temperature, long liquid ranges, and marked hydrolytic and thermal stabilities.
- Ye, Chengfeng,Shreeve, Jean'ne M.
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p. 6511 - 6513
(2007/10/03)
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- THE EFFECT OF POLYMERIC AND MODEL IMIDAZOLIUM HALIDES ON THE RATE OF HYDROLYSIS OF 4-ACETOXY-3-NITROBENZOIC ACID
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The course of hydrolysis of an ester, 4-acetoxy-3-nitrobenzoic acid catalyzed with poly(1-methyl-3-allylimidazolium bromide) (IIa), poly (IIb) and poly (IIc) in a 28.5percent aqueous ethanol was investigated as a function of pH and compared with low-molecular weight models, viz., 1-methyl-3-alkylimidazolium bromides (the alkyl group being methyl, propyl, and hexyl, resp).Polymers IIb, IIc possessed a higher activity at pH above 9, while the models were more active at a lower pH with a maximum at pH 7.67.The catalytic activity at the higher pH is attributed to an attack by the OH- group, while at the lower pH it is assigned to a direct attack of water on the substrate.The rate of hydrolysis of 4-acetoxy-3-nitrobenzoic acid is proportional to the catalyst concentration and proceeds as a first-order reaction.The hydrolysis depends on the composition of the solvent and was highest at 28.5percent (vol.) of ethanol in water.The hydrolysis of a neutral ester, 4-nitrophenyl acetate, was not accelerated by IIc.
- Sorm, Miloslav,Prochazka, Miloslav,Kalal, Jaroslav
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p. 845 - 853
(2007/10/02)
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