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.
Highlights
IntroductionThe 2-azido-1,3-dimethoxyimidazolium [1] and 2-azido-1,3-dimethylimidazolinium [2]
The 2-azido-1,3-dimethoxyimidazolium [1] and 2-azido-1,3-dimethylimidazolinium [2]ions were synthesized from the respective 2-bromo or 2-chloro compounds and sodium azide.This pathway is only viable when the halogen derivatives are readily available
One crystal structure of a cationic triazatrimethine cyanine chromophore derived from benzimidazole has been reported [12]
Summary
The 2-azido-1,3-dimethoxyimidazolium [1] and 2-azido-1,3-dimethylimidazolinium [2]. Ions were synthesized from the respective 2-bromo or 2-chloro compounds and sodium azide. This pathway is only viable when the halogen derivatives are readily available. A different approach to azidoazoles involves fragmentation of sulfonyltriazenes [3], which can be accessed by azidation of azole anions. Triazene formation is accomplished by reaction of imidazolin-2-ylidenes with alkyl or aryl azides [4,5], and a series of triazene crystal structures of this type are known [4,5,6,7,8,9,10,11]. We intended to combine the azidation of a carbene with the fragmentation of a sulfonyltriazene
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