Structure and Properties of High Stability Geminal Dicationic Ionic Liquids
Top Cited Papers
- 23 December 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (2), 593-604
- https://doi.org/10.1021/ja046521u
Abstract
Thirty-nine geminal dicationic ILs were synthesized and characterized in terms of their surface tensions, densities, melting points, refractive indices, viscosities, and miscibilities with a polar and nonpolar solvent. Two imidazolium or pyrrolidinium cations were joined via different length hydrocarbon linkage chains (from 3 to 12 carbons long). The various geminal dications were paired with up to four different anions. The effect of the dication type, linkage chain, alkyl substituents, and anion type on the physicochemical properties of these compounds was examined. Among the more interesting findings for this class of compounds was that their liquid and thermal stability ranges generally exceeded those of the more conventional, better known ILs. Indeed, this range was from −4 to >400 °C for one of the pyrrolidinium-based geminal dicationic liquids. X-ray crystallography of the smaller solid ionic compounds indicated that there may be a correlation between the configurational degrees of freedom of the ILs and their melting points/glass transition temperatures. In one case, the crystal structure showed that a dicationic moiety had three distinct conformations in an asymmetric unit cell. The solvation properties of the geminal dicationic ILs tend to be similar to those of their monocationic analogues.Keywords
This publication has 17 references indexed in Scilit:
- Ionic liquids—weakly-coordinating solvents for the biphasic ethylene oligomerization to α-olefins using cationic Ni-complexesJournal of Molecular Catalysis A: Chemical, 2004
- Properties of ionic liquid solvents for catalysisJournal of Molecular Catalysis A: Chemical, 2004
- Why Is CO2 So Soluble in Imidazolium-Based Ionic Liquids?Journal of the American Chemical Society, 2004
- Switching Potentials and Conductivity of Polypyrrole Films Prepared in the Ionic Liquid 1-Butyl-3-methylimidazolium HexafluorophosphateJournal of the Electrochemical Society, 2004
- Predicting melting points of quaternary ammonium ionic liquidsElectronic supplementary information (ESI) available: training sets B and C. See http://www.rsc.org/suppdata/gc/b3/b301217d/Green Chemistry, 2003
- Viscosity and Density of 1-Alkyl-3-methylimidazolium Ionic LiquidsPublished by American Chemical Society (ACS) ,2002
- Room-Temperature Ionic Liquids. Solvents for Synthesis and CatalysisChemical Reviews, 1999
- Hydrophobic, Highly Conductive Ambient-Temperature Molten SaltsInorganic Chemistry, 1996
- A matrix-operator approach to reflection high-energy electron diffraction theoryActa Crystallographica Section A Foundations of Crystallography, 1995
- Conductivities of AlCl3 ‐ Rich Molten AlCl3 ‐ LiCl MixturesJournal of the Electrochemical Society, 1979