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Updated: Aug 6, 2026

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
Published on: March 24, 2018
Syntheses and characterization of unsymmetric dicationic salts incorporating imidazolium and triazolium
Ruihu Wang1, Chuan-Ming Jin, Brendan Twamley
1Department of Chemistry, University of Idaho, Moscow, ID 83844-2343, USA.
Abstract:
A series of both imidazolium- and triazolium-based unsymmetric dicationic salts with alkyl and polyfluoroalkyl substituents were prepared and characterized. Most of them can be classified as ionic liquids (MP < 100 degrees C). Key physical properties, such as melting point, thermal stability, density, and solubility in common solvents were determined and were compared with those of the related monocationic imidazolium- or triazolium-based salts. The effects of anions and substituents bonded to the triazolium and imidazolium cations on these properties were examined. 1-(3-Butyl-imidazolium-1-yl)methylene-(4-butyl-1,2,4-triazolium diiodide) (2d), the precursor of 1-(3-butylimidazolium-1-yl)methylene-(4-butyl-1,2,4-triazolium) bi[bis(trifluoromethanesulfonyl)amide] (3d), reacted with Pd(OAc)(2) at 120 degrees C to generate a binuclear palladium(II) dicarbene complex. The palladium(II) complex was characterized by single-crystal X-ray diffraction analysis and was used as a catalyst precursor for palladium-catalyzed Heck cross-coupling reactions in 3d. Preliminary results show that 3d could serve as both the solvent and catalyst support in the catalytic reactions.
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