Imidazole → Perylene

Participants

Reaction Conditions

Reaction Steps

In an autoclave of capacity 100 ml, a mixture of 3.66 g (9.34 mmol) of perylene-3,4,9,10-tetracarboxylic dianhydride, 18.7 g of imidazole, 1.32 g of zinc acetate dihydrate, 8.0 ml (450 mmol) of water and 1.05 g (5.12 mmol) of 2,5-di-tert-butylaniline (prepared according to Rec. Trav. Chim. Pays-Bas, 1958, 77, 491) is heated at 210° C. for 23 h. After the end of the reaction, the mixture is removed from the autoclave by rinsing with ethanol, treated with water and concentrated hydrochloric acid and boiled until all the ethanol has evaporated. The brown-red residue is filtered off with suction and boiled in 10 per cent potassium carbonate solution for 1 h. The residue is filtered off with suction, dried at 120° C. in a drying cabinet and chromatographed on silica gel using chloroform. This gives a forerun (yellow, blue fluorescence) of perylene, followed by N-(2,5-di-tert-butylphenyl)perylene-3,4-dicarboximide (2b) and then by N,N'-bis(2,5-di-tert-butylphenyl)perylene-3,4,9,10-tetracarboximide (1b). Yield 2.40 g (50.5%), m.p. >300° C. Rf (CHCl3 /silica gel)=0.85. UV (CHCl3): λmax (ε)=489 nm (35300), 512 (33590). Fluorescence (CHCl3,exc. 489 nm) λmax (Irel)=535 nm (1), 576 nm (0.36).

Provenance & Evidence