Imidazole → N-(1-Octylnonyl)perylene-3,4-dicarboximide

Participants

Reaction Steps

1.4 g (3.1 mmol) of perylene-3,4,9,10-tetracarboxylic dianhydride, 6.1 g of imidazole, 960 mg (3.7 mmol) of 9-aminoheptadecane (prepared according to DE-A 4,007,618), 150 mg (0.68 mmol) of zinc acetate dihydrate and 3.0 ml (170 mmol) of water are heated in an autoclave (100 ml) at 190° C. for 24 h. Workup is analogous to that used for preparing 2b. Yield 130 mg (7% by extractive recrystallization from methanol, such as described in Chem. Ber. 1985, 118, 4641) orange red crystals showing strong solid fluorescence, m.p. 143°-143.6° C. Rf (CHCl3 /silica gel)=0.94. UV (CHCl3): λmax (ε)=454 nm (sh, 17620), 485 (32530), 508 (29480). Fluorescence (CHCl3, exc. 485 nm): λmax (Irel)=572 (sh, 0.49), 536 (1).

Provenance & Evidence