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Crystals 2016, 6(4), 40; doi:10.3390/cryst6040040

2-Azidoimidazolium Ions Captured by N-Heterocyclic Carbenes: Azole-Substituted Triazatrimethine Cyanines

1
Faculty of Chemistry and Pharmacy, University of Innsbruck, Innsbruck 6020, Austria
2
Institute of Mineralogy and Petrography, University of Innsbruck, Innsbruck 6020, Austria
3
Research Institute for Textile Chemistry and Textile Physics, University of Innsbruck, Dornbirn 6850, Austria
*
Author to whom correspondence should be addressed.
Academic Editor: Helmut Cölfen
Received: 29 January 2016 / Revised: 15 February 2016 / Accepted: 17 February 2016 / Published: 8 April 2016
(This article belongs to the Special Issue Nitrogen-Rich Salts)
View Full-Text   |   Download PDF [2063 KB, uploaded 8 April 2016]   |  

Abstract

1,3-Disubstituted 2-azidoimidazolium salts (substituents = methyl, methoxy; anion = PF6) reacted with N-heterocyclic carbenes to yield yellow 2-(1-(azolinylidene)triazen-3-yl)-1,3-R2-imidazolium salts (azole = 1,3-dimethylimidazole, 1,3-dimethoxyimidazole, 4-dimethylamino-1-methyl-1,2,4-triazole; R = methyl, methoxy; anion = PF6). Crystal structures of three cationic triazenes were determined. Numerous interionic C–H···F contacts were observed. Solvatochromism of the triazenes in polar solvents was investigated by UV-Vis spectroscopy, involving the dipolarity π* and hydrogen-bond donor acidity α of the solvent. Cyclovoltammetry showed irreversible reduction of the cations to uncharged radicals. Thermoanalysis showed exothermal decomposition. View Full-Text
Keywords: azide; carbene; cyanine; cyclovoltammetry; imidazole; thermoanalysis; triazene; triazole; UV-Vis spectroscopy azide; carbene; cyanine; cyclovoltammetry; imidazole; thermoanalysis; triazene; triazole; UV-Vis spectroscopy
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MDPI and ACS Style

Haslinger, S.; Laus, G.; Kahlenberg, V.; Wurst, K.; Bechtold, T.; Vergeiner, S.; Schottenberger, H. 2-Azidoimidazolium Ions Captured by N-Heterocyclic Carbenes: Azole-Substituted Triazatrimethine Cyanines. Crystals 2016, 6, 40.

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