1-Iodonaphthalene → 5,11-Di-1-naphthyl-5,11-dihydroindolo[3,2-b]carbazole

Participants

Reaction Conditions

Reaction Steps

A 200 milliliter 3-necked round bottom flask equipped with a mechanical stirrer, reflux condenser, and argon inlet was purged with argon and then charged with 5,11-dihydroindolo[3,2-b]carbazole (5.1 grams, 0.02 mol), 1-iodonaphthalene (10.16 grams, 0.04 mol), copper sulfate pentahydrate (0.25 gram, 1.0 mmol), potassium carbonate (5.52 grams, 0.04 mol), and n-tridecane (5.0 milliliters). Under an argon atmosphere, the reaction mixture was heated to about 250° C. with a heating mantle and allowed to proceed at this temperature to completion in about 6 hours. The reaction mixture was cooled to about 100° C., and 100 milliliters of toluene and 15 milliliters of water were then added with vigorous stirring for 30 minutes. The resulting two phase mixture was transferred into a separatory funnel and the layers separated. The organic phase which contains the desired product was washed with water, treated with 25 grams of alumina under an argon atmosphere, and filtered. The filtrate was then evaporated and the residue was recrystallized from toluene to provide 2.5 grams of pure, about 99.9 percent, 5,11-di-1-naphthyl-5,11-dihydroindolo[3,2-b]carbazole (3).

Provenance & Evidence