Potassium Carbonate → 5,11-Bis(4-methylphenyl)indolo[3,2-b]carbazole

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A mixture of 5,11-dihydridoindolo[3,2-b]carbazole (2.56 g, 10 mmol), 18-crown-6 (0.52 g, 2.0 mmol), K2CO3 (11.06 g, 80 mmol), 4-iodotoluene (6.54 g, 30 mmol), copper (2.54 g, 40 mmol), and 1,2-dichlorobenzene (40 mL) was charged into an argon-filled 200 mL flask fitted with a condenser. The mixture was heated under reflux in an argon atmosphere for 24 h. Subsequently, the reaction mixture was cooled down to room temperature, diluted with toluene, and filtered. The solid was stirred in 50 mL of N,N-dimethylformamide and 50 mL of 2N HCl was added dropwise and the mixture was stirred for 30 min. The yellow suspension was decanted and filtered to give a yellow solid. The solid was then stirred in a mixture of DMSO (200 mL) and 20% NaOH (50 mL) for 30 min and then filtered. The solid was washed with deionized water, methanol, and dried to yield 1.65 g of 5,11-bis(4-methylphenyl)indolo[3,2-b]carbazole, which was then subject to train sublimation to obtain electrically pure compound for OTFT fabrication. DSC showed two endotherms at 305° C. and 322° C. on first heating. 1H NMR (CDCl3): δ 8.11 (d, J=7.8 Hz, 2H), 8.04 (s, 2H), 7.57 (d, J=8.3 Hz, 4H), 7.48 (d, J=8.3 Hz, 4H), 7.39 (d, J=3.7 Hz, 4H), 7.21 (m, 2H), 2.54 (s, 6H); IR (NaCl): 3034, 2916, 1606, 1515, 1451, 1323, 1235, 1191, 819, 741 cm−1.

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