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1,1'-DIETHYL-4,4'-CARBOCYANINE IODIDE is dark green fine crystalline powder

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Organic dye, soluble, used as a chemical shutter in laser operation.

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1,1'-DIETHYL-4,4'-CARBOCYANINE IODIDE is a cationic C3-cyanine type compound with 1-ethylquinolin-4-yl groups at both ends.

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The putative mitochondria-targeted cryptocyanine (Mito-CCy) and a non-targeted cryptocyanine (CCy) control were synthe- sized as outlined in Figure 1. Briefly, the synthesis entailed the alkylation of 4-methylquinoline with 4-bromomethylbenzoic acid to yield 3, which was further reacted with N,N′-diphenyl- formamidine and acetic anhydride to produce 2. Extension of the π-conjugated system 2 with 3 and triethylamine (TEA) re- sulted in cryptocyanine 1. The amide-linked target compound, Mito-CCy, was obtained from 1 by reacting with (PPh3+(CH2)2NH2)Br? in the presence of 2-(1H-9-azobenzo-tri- azole-1-yl)-1,1,3,3-tetramethylammonium hexafluorophos- phate (HATU), diisopropylethylamine (DIPEA) and TEA in N,N-dimethylformamide (DMF). CCy, an analogue lacking the TPP unit, was prepared using an analogous procedure. Both Mito-CCy and CCy and gave 1H NMR and 13C NMR spectral and ESI-MS analytical data consistent with their proposed structures.

Figure 1. Synthesis of Mito-CCy and CCy. (i) Triphenylphosphine, acetonitrile, reflux, 24 h, 88%; (ii) 4-(bromomethyl)benzoic acid, acetonitrile, 110 °C, 6 h, 72%; (iii) N,N′-diphenylformamidine, acetic anhydride, 150 °C, 1 h, 87%; (iv) 3, TEA, dichloromethane, 25 °C, 24 h, 48%; (v) propylamine, HATU, TEA, DIPEA, DMF, r.t., 24 h, 32%; (vi) 4, HATU, TEA, DIPEA, DMF, r.t., 24 h, 35%.

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Store at -20°C away from light, under an inert gas atmosphere (e.g. nitrogen) to prevent oxidative degradation. Repeated freeze-thaw cycles or high temperatures (>75°C) may cause decomposition.

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Cryptocyanine ?? ??: