The irreversible dimerization of the acetophenone radical anion, chosen as an example of a carbon-carbon coupling reaction between two charged species, was investigated in a series of 1,3-dialkylimidazolium and 1,2,3-trialkylimidazolium ionic liquids. Indeed, such ion dimerizations which display slow kinetics despite small activation energies, are controlled by a subtle competition between bond...

Imidazolium-based ionic liquids that contain perrhenate anions are very efficient reaction media for the epoxidation of olefins with H2O2 as an oxidant, thus affording cyclooctene in almost quantitative yields. The mechanism of this reaction does not follow the usual pathway through peroxo complexes, as is the case with long-known molecular transition-metal catalysts. By using in situ Raman, FT...

Ionic liquids based on 1-alkyl-3-methylimidazolium cations and the hydrogen sulfate (or bisulfate) anion, HSO(4)(-), are much more viscous than ionic liquids with alkyl sulfates, RSO(4)(-). The structural origin of the high viscosity of HSO(4)(-) ionic liquids is unraveled from detailed comparison of the anion Raman bands in 1-ethyl-3-methylimidazolium hydrogen sulfate and 1-butyl-3-methylimida...

Macrocycles based on neutral calixarenes and calixpyrroles have been extensively explored for ion binding, molecular assembly and related applications. Given that only these two types of calix compounds and their analogs are available, the introduction of new forms of widely usable calix macrocycles is an outstanding challenge. Here we report the quadruply/quintuply charged imidazole-based homo...

The effects of interionic hydrogen bonding and π-π stacking interactions on the physical properties of a new series of picrate anion based ionic liquids (ILs) have been investigated experimentally and theoretically. The existence of aromatic (C2-HO) and aliphatic (C7-HO-N22 and C6-HO-N20) hydrogen bonding and π-π stacking interactions in these ILs has been observed using various spectroscopic t...

Imidazolium, pyridinium, pyrrolidinium, piperidinium, morpholinium, and quaternary ammonium bis(trifluoromethylsulfonyl)imide salts were functionalized with a carboxyl group. These ionic liquids are useful for the selective dissolution of metal oxides and hydroxides. Although these hydrophobic ionic liquids are immiscible with water at room temperature, several of them form a single phase with ...

Aluminum is the most earth-abundant metal, trivalent, inert in ambient humid air, and has a density approximately four-times that of lithium at room temperature. These attributes make it an attractive material for cost-effective, long-duration storage electrical energy batteries. Scientific discoveries past decade have established secondary Al batteries can be created by paring anode with graph...

Two methylene-bridged bis(imidazolium) salts [H4L](PF6)2 and [H4L](PF6)2 with appended amide groups have been synthesized which, after deprotonation, may serve as potentially tetradentate ligands providing two bis(imidazole-2-ylidene) and two amide donors. Using [H4L](PF6)2, a square-planar nickel(II) complex [NiL1] and a six-coordinate bis(ligand) iron(II) complex [Fe(HL)2] have been isolated ...

Al-based batteries are considered an attractive alternative to Li metal due the use of Al as anode with lower cost, reactivity and larger abundance compared Li. Despite aforementioned attributes, few electrolytes permit reversible electrodeposition at room temperature. Thus, for last 30 years, expensive imidazolium-based ionic liquids have dominated field. Even though extensive research has bee...