Benzimidazolium dyes

Wang S, Chang YT (2006) Combinatorial synthesis of benzimidazolium dyes and its diversity directed application toward GTP-selective fluorescent chemosensors. J Am Chem Soc 128 10380-10381... 

Positively charging CCAs are organic molecules with a positive charge. Colored positive CCAs tend to be the black Nigrosine dyes, which are mixtures of compounds in which highly arylated phenazines (8) are the major component. Colorless positive CCAs tend to contain a quaternary nitrogen atom cetylpyridi-nium chloride (9), also found in antiseptic mouthwashes, is one of the most widely used [2,3], Triphenylmethane, benzimidazolium and beta di- and tri-car-bonyl compounds are also used [6],... 

The heterocyclic quaternary salt l,3-diethyl-2-methyl-5-(iV-trifluoromethylsul-fonyl -trifluoromethylsulfoximido)-l -benzimidazolium tosylate, containing the superstrong electron acceptor (ap = 1.4) group CF3S(0)=NS0 2CF 3, was prepared and used as an intermediate for carbocyanine, merocyanine, and styryl dyes. The spectra of these dyes showed a large bathochromic shift compared with the... 

The l,3-dimethyl-2-substituted styryl benzimidazolium salts (xxxii), a useful hemocyanine dyes have been synthesized by the solvent free microwave assisted condensation of 1,2,3-trimethyl benzimidazole salts with aromatic aldehydes in the presence of piperidine [38]. 

Fig. 17.16 Synthesis of benzimidazolium hemicyanine dyes. Reagents and conditions (a) triethyl orthoacetate, H+, toluene, reflux (b) KOH, Mel, acetone (c) Tf20, poly(4-vinylpyridine), DCM (d) 4, DCM (e) 48% HBr, 65°C (f) 2-chlorotrityl alcohol resin sequentially treated with thionyl chloride in DCM and ethylene diamine in DCM (g) 8, HATU, DIPEA, 30% DMF/DCM (h) R-CHO (96-aromatic aldehydes), pyrrolidine, NMP (i) 5% TFA/DCM...

CA Index Name l//-Benzimidazolium, 5,6-dichloro-2-[3-(5,6-dichloro-l,3-diethyl-l,3-dihydro-2//-benzimida-zol-2-ylidene)-l-propen-l-yl]-l,3-diethyl-, iodide (1 1) Other Names l//-Benzimidazolium, 5,6-dichloro-2-[3-(5,6-dichloro-l,3-diethyl-l,3-dihydro-2//-benzimida-zol-2-ylidene)-l-propenyl]-1,3-diethyl-, iodide 5,6-Di-chloro-2-[3-(5,6-dichloro-l,3-diethyl-2-benzimidazoli-nylidene)propenyl] -1,3 -diethylbenzimidazolium iodide Benzimidazolium, 5,6-dichloro-2-[3-(5,6-dichloro-l,3-diethyl-2-benzimidazolinylidene)propenyl]-1,3-diethyl-, iodide Benzimidazolocarbocyanine iodide, 5,5, 6,6 -tet-rachloro-l,l, 3,3 -tetraethyl- Imidacarbocyanine iodide, 1, l, 3,3 -tetraethyl-5,5, 6,6 -tetrachloro- 1, l, 3,3 -Tetra-ethyl-5,5, 6,6 -tetrachlorobenziimdazolocarbocyanine iodide 1, l, 3,3 -Tetraethyl-5,5, 6,6 -tetrachloroimidacar-bocyanine iodide 5,5, 6,6 -Tetrachloro-l,l, 3,3 -tetra-ethylbenzimidazolocarbocyanine iodide Bis(5,6-di-chloro-1,3-diethyl-2-benziimdazole)trimethinecyanine iodide CBIC2 JC 1 NK 1420 Merck Index Number Not listed Chemical/Dye Class Cyanine Molecular Formula C25H27CI4IN4... 

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