Imidazolium ionic liquids: A simple anion exchange protocol

Dinarés, Immaculada; Miguel, Cristina Garcia de; Ibáñez, Anna; Mesquida, Neus; Alcalde, Ermitas

doi:10.1039/b915743n

Cited by 92 publications

(70 citation statements)

References 52 publications

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“…34 Compound 2a was subjected to anion exchange using a basic resin Amberlite IRA-400 with chloride sites. The resin (15.9 g for 0.0037 mol of 2a) was washed with water.…”

Section: Methodsmentioning

confidence: 99%

“…In order to carry out the anion exchange, the most widely used metathetic reaction was used to obtain the bistrifylimide derivative. 33 Indeed, most of the salts used in this work showed a very low solubility in conventional organic solvents and we used a previously reported exchange protocol on resin, 34 converting the bromide (2a) into the corresponding hydroxide that was subsequently neutralised in the presence of conjugate acids of the anions. According to previous reports, this procedure allowed us to obtain the organic salts with high yields and avoid the use of large volumes of organic solvents.…”

Section: Organic and Biomolecular Chemistrymentioning

confidence: 99%

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Solution and thermal behaviour of novel dicationic imidazolium ionic liquids

et al. 2013

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A new class of functionalised dicationic ionic liquids, containing a central cationic unit capped by a basic functionality (imidazole), has been synthesised. These salts have been characterised in isotropic solution using proton and 2D-NMR spectroscopy, and their thermal stability has been studied by DSC and TGA. All these novel salts contain the 1-(1-imidazolylmethyl)-3,5-di{1-(3'-octylimidazolylmethyl)}-benzene cation as a defining structural motif. Salts of both singly and doubly charged anions were prepared and, in particular, the selected monoanions (Br − , [BF 4 ] − , or [NTf 2 ] − ) differ in size, shape and hydrogenbonding ability, whereas the dianions differ in the nature of the spacer, such as 1,4-benzenedicarboxylate, 2,6-naphthalenedicarboxylate, 1,5-and 2,6-naphthalenedisulfonate, 1,4-butanedicarboxylate, and 1,6-hexanedicarboxylate. These ionic liquids exhibit the presence of different conformers in solution, whose distribution is affected by the nature of the anion. The nature of the anion also affects their thermal stability.

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“…34 Compound 2a was subjected to anion exchange using a basic resin Amberlite IRA-400 with chloride sites. The resin (15.9 g for 0.0037 mol of 2a) was washed with water.…”

Section: Methodsmentioning

confidence: 99%

Section: Organic and Biomolecular Chemistrymentioning

confidence: 99%

Solution and thermal behaviour of novel dicationic imidazolium ionic liquids

et al. 2013

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“…After filtration on neutral aluminum oxide and concentration in vacuo, the desired salt was obtained. General procedure for the synthesis of the naphthalenedisulfonate salts (1 b, c and 2 b, c) [27] A column packed with anion-exchange Amberlite resin IRA-400 (chloride form, 11.50 g) was used. To convert the chloride form of the resin into the hydroxide form, it was first washed with an aqueous solution of NaOH (570 mL, 10 % w/v) and subsequently with water until the eluate was neutral.…”

Section: Methodsmentioning

confidence: 99%

The Gelling Ability of Some Diimidazolium Salts: Effect of Isomeric Substitution of the Cation and Anion

et al. 2013

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The gelling ability of some geminal imidazolium salts was investigated both in organic solvents and in water solution. Organic salts differing either in the cation or anion structure were taken into account. In particular, the effects on the gel‐phase formation of isomeric substitution on the cation or anion as well as of the use of mono‐ or dianions were evaluated. As far as the cation structure is concerned, isomeric cations, such as 3,3′‐di‐n‐octyl‐1,1′‐(1,4‐phenylenedimethylene)diimidazolium and 3,3′‐di‐n‐octyl‐1,1′‐(1,3‐phenylenedimethylene)diimidazolium, were used. On the other hand, in addition to the bromide anion, isomeric dianions, such as the 1,5‐ and 2,6‐naphthalenedisulfonate anions, were also examined. After preliminary gelation tests, different factors affecting the obtained gel phases, such as the nature of the solvent, organogelator concentrations, and action of external stimuli, were analyzed. The gel‐phase formation was also studied as a function of time, by using resonance light scattering measurements. Gel morphologies were analyzed by scanning electron microscopy. To further support the understanding of the different behavior shown by the isomeric cations, some representative ion pairs were analyzed by DFT‐based investigations. The collected data underline the significant role played by isomeric substitution of both cation and anion structures in determining the gelling capability of the investigated salts, as well as the properties of the gel phases. Finally, DFT investigations were helpful in the identification of the structural features affecting the self‐assembly.

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“…The use of inorganic acids instead of salts is a potential approach to reducing these inorganic contaminations. 28 In the case of a large number of inorganic or organic anions, alternatives need to be considered, due to the fact that an anion exchange by weaker acids than hydrohalic acids 29 cannot be efficiently performed. In the case of imidazolium cations, Earle and Seddon proposed the use of imidazole carbenes 30 as strong bases.…”

Section: Introductionmentioning

confidence: 99%

Development of novel ionic liquids based on ampicillin

et al. 2012

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Novel ionic liquids containing ampicillin as an active pharmaceutical ingredient anion were prepared with good yields by using a new, efficient synthetic procedure based on the neutralization of a moderately basic ammonia solution of ampicillin with different organic cation hydroxides. The relevant physical and thermal properties of these novel ionic liquids based on ampicillin were also evaluated.

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Imidazolium ionic liquids: A simple anion exchange protocol

Cited by 92 publications

References 52 publications

Solution and thermal behaviour of novel dicationic imidazolium ionic liquids

Solution and thermal behaviour of novel dicationic imidazolium ionic liquids

The Gelling Ability of Some Diimidazolium Salts: Effect of Isomeric Substitution of the Cation and Anion

Development of novel ionic liquids based on ampicillin

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