Acoustic levitation and infrared thermography: a sound approach to studying droplet evaporation.

Herein we report a new technique combining acoustic levitation and infrared thermography to directly monitor droplet surface temperatures. Using it, temperature profiles were recorded during the evaporation of deionized water, methanol, n-propanol, and isopropanol. Results support the viability of this inexpensive and easily-accessed technique for studying chemical and physical changes in droplets.

3-(1-Methyl-3-imidazolio)propane-sulfonate: a precursor to a Brønsted acid ionic liquid.

The title compound, C(7)H(12)N(2)O(3)S, is a zwitterion precursor to a Brønsted acid ionic liquid with potential as an acid catalyst. The C-N-C-C torsion angle of 100.05 (8)° allows the positively charged imidazolium head group and the negatively charged sulfonate group to inter-act with neighboring zwitterions, forming a C-H⋯O hydrogen-bonding network; the shortest among these inter-actions is 2.9512 (9) Å. The C-H⋯O inter-actions can be described by graph-set notation as two R(2) (2)(16) and one R(2) (2)(5) hydrogen-bonded rings.

In search of ionic liquids incorporating azolate anions.

Twenty-eight novel salts with tetramethyl-, tetraethyl-, and tetrabutylammonium and 1-butyl-3-methylimidazolium cations paired with 3,5-dinitro-1,2,4-triazolate, 4-nitro-1,2,3-triazolate, 2,4-dinitroimidazolate, 4,5-dinitroimidazolate, 4,5-dicyanoimidazolate, 4-nitroimidazolate, and tetrazolate anions have been prepared and characterized by using differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), and single-crystal X-ray crystallography. The effects of cation and anion type and structure on the physicochemical properties of the resulting salts, including several ionic liquids, have been examined and discussed. Ionic liquids (defined as having m.p.<100 degrees C) were obtained with all combinations of the 1-butyl-3-methylimidazolium cation ([C(4)mim](+)) and the heterocyclic azolate anions studied, and with several combinations of tetraethyl or tetrabutylammonium cations and the azolate anions. The [C(4)mim](+) azolates were liquid at room temperature exhibiting large liquid ranges and forming glasses on cooling with glass-transition temperatures in the range of -53 to -82 degrees C (except for the 3,5-dinitro-1,2,4-triazolate salt with m.p. 33 degrees C). Six crystal structures of the corresponding tetraalkylammonium salts were determined and the effects of changes to the cations and anions on the packing of the structure have been investigated.

Approaches to crystallization from ionic liquids: complex solvents-complex results, or, a strategy for controlled formation of new supramolecular architectures?

There are now more than 1200 papers a year describing research results using the 'neoteric' solvents, known as ionic liquids (ILs). If ILs are such highly studied solvents, why has there been so comparatively little research in their use in crystallization? Here we explore this question and discuss possible strategies for utilization of the mundane and the unique aspects of ILs for novel crystallization strategies including crystallization of high and low melting solids using thermal shifts; "solvothermal" techniques; slow diffusion; electrocrystallization; and use of a co-solvent. The results presented here and those appearing in the literature indicate both the complex nature of these solvents and their promise in delivering unique solvation, metal ion coordination numbers, coordination polymer motifs, and metal-anion interactions, to name but a few. These complex, but fascinating, results and the promise of much more intimate control over crystallization processes will drive a growing interest in using ILs as crystallization solvents.

Exploiting isolobal relationships to create new ionic liquids: novel room-temperature ionic liquids based upon (N-alkylimidazole)(amine)BH2+"boronium" ions.

Readily prepared imidazole-based boronium ions form stable, hydrophobic, room-temperature ionic liquids (RTIL) with unique electronic and spectroscopic characteristics.

1-butyl-3-methylimidazolium 3,5-dinitro-1,2,4-triazolate: a novel ionic liquid containing a rigid, planar energetic anion.

The novel ionic liquid, 1-butyl-3-methylimidazolium 3,5-dinitro-1,2,4-triazolate has been synthesized and exhibits an unexpectedly low melting point (35 degrees C) considering the size and shape of the rigid, planar anion; analogous tetraalkylammonium salts (methyl, ethyl and n-butyl) have also been prepared and the tetraethylammonium example was characterized by single crystal X-ray diffraction.

Crystal structures of imidazolium bis(trifluoromethanesulfonyl)imide 'ionic liquid' salts: the first organic salt with a cis-TFSI anion conformation.

Crystal structures of two examples of an important class of ionic liquids, 1,3-dimethylimidazolium and 1,2,3-triethylimidazolium bis(trifluoromethanesulfonyl)imide have been characterized by single crystal X-ray diffraction. The anion in the 1,3-dimethylimidazolium example (mp 22 degrees C), adopts an unusual cis-geometry constrained by bifurcated cation-anion C-H. . .O hydrogen-bonds from the imidazolium cation to the anion resulting in the formation of fluorous layers within the solid-state structure. In contrast, in the 1,2,3-triethylimidazolium salt (mp 57 degrees C), the ions are discretely packed with only weak C-H. . .O contacts between the ions close to the van der Waals separation distances, and with the anion adopting the twisted conformation observed for all other examples from the limited set of organic bis(trifluoromethanesulfonyl)imide crystal structures. The structures are discussed in terms of the favorable physical properties that bis(trifluoromethanesulfonyl)imide anions impart in ionic liquids.

1,3-dimethylimidazolium-2-carboxylate: the unexpected synthesis of an ionic liquid precursor and carbene-CO2 adduct.

1,3-Dimethylimidazolium-2-carboxylate is formed in good yield, rather than the anticipated organic salt, 1,3-dimethylimidazolium methyl carbonate, as the reaction product resulting from both N-alkylation and C-carboxylation of 1-methylimidazole with dimethyl carbonate; the crystal structure of the zwitterion exhibits pi-stacked rings and two-dimensional sheets constructed by hydrogen-bonds from imidazolium-ring hydrogens to the carboxylate group.

Liquid clathrate formation in ionic liquid-aromatic mixtures.

1-Alkyl-3-methylimidazolium containing ionic liquids with hexafluorophosphate, bis(trifyl)imide, tetrafluoroborate, and chloride anions form liquid clathrates when mixed with aromatic hydrocarbons; in the system 1,3-dimethylimidazolium hexafluorophosphate-benzene, the aromatic solute could be trapped in the solid state forming a crystalline 2:1 inclusion compound.

Conventional free radical polymerization in room temperature ionic liquids: a green approach to commodity polymers with practical advantages.

Free-radical polymerization of methyl methacrylate and styrene using conventional organic initiators in the room temperature ionic liquid, 1-butyl-3-methylimidazolium hexafluorophosphate ([C4mim][PF6]) is rapid and produces polymers with molecular weights up to 10x higher than from benzene; both polymerization and isolation of products were achieved without using VOCs, offering economic as well as environmental advantages.

Task-specific ionic liquids incorporating novel cations for the coordination and extraction of Hg2+ and Cd2+: synthesis, characterization, and extraction studies.

A series of hydrophobic task-specific ionic liquids designed to extract Hg2+ and Cd2+ from water were prepared by appending urea-, thiourea-, and thioether-substituted alkyl groups to imidazoles and combining the resulting cationic species with PF6-. The new ionic liquids were characterized and investigated for their metal ion extraction capabilities. When used in liquid/liquid extraction of Hg2+ and Cd2+ from aqueous solutions, the metal ion distribution ratios increased several orders of magnitude, regardless of whether the ionic liquids were used as the sole extracting phase or doped into a series of [1-alkyl-3-methylimidazolium][PF6] (alkyl = n-C4-C8) ionic liquids to form a 1:1 solution. In the 1:1 mixtures, as the length of the alkyl chain increased from butyl to hexyl to octyl, the metal ion distribution ratios increased. Increasing the ratio TSIL/[C4mim][PF6] resulted in higher distribution ratios for both Hg2+ and Cd2+. Overall, the thiourea- and urea-derivatized cations yielded the highest distribution ratios, and those for Hg2+ were higher than those for Cd2+; however, a change in aqueous-phase pH does not promote the stripping of metal ions from the extracting phase. The combination of these imidazolium cations and PF6- produced ionic liquids with decreased thermal stability in comparison to [C(n)mim]-[PF6]. Gaussian98 restricted Hartree-Fock geometry optimizations for one of the thiourea-appended cations shows the charge delocalization around the ring and suggests that the thiourea group may aid in deprotonating the imidazolium ring and may be responsible for the lowered thermal stability of these cations.