Imidazole → N-(2,5-Di-t-butyl-4-nitrophenyl)perylene-3,4-dicarboximide

関与物質

反応条件

反応手順

0.20 g (0.93 mmol) of perylene-3,4-dicarboxylic anhydride is mixed with 0.47 g (1.9 mmol) of 2,5-di-t-butyl-4-nitroaniline, 0.20 g of zinc acetate dihydrate and 4 g of imidazole, and the mixture is heated under argon at 170° C. for 22 h. The product is removed from the flask by washing with ethanol, treated with 2N hydrochloric acid and then boiled until all the ethanol has evaporated. The solid product is filtered off with suction, washed twice with water and then boiled in 10% potassium carbonate solution. The reaction product is again filtered off with suction while hot and washed several times with hot water until the filtrate run-off is no longer yellow. The residue is dried in a drying cabinet at 120° C. and then chromatographed on silica gel using toluene. The solution thus obtained is filtered through a D5 sintered crucible in order to remove any adhering silica gel. Yield 0.09 g (26%) of a red powder showing a red solid fluorescence, m.p. >360° C., Rf (CHCl3 /silica gel)=0.31, UV (CHCl3): λmax (ε)=514 (24450), 489 (25850), 356 (3100), 265 (33790). Fluorescence (CHCl3): λmax (Ired)=543 (1), 576 (0.45).

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