N,N,N'-triphenyl-4-phenylenediamine → 3-[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole

Participants

Reaction Conditions

Reaction Steps

Specifically, 627.64 mg (1.7 mmol) of 3-iodine-9-phenylcarbazole, 672.86 mg (2.0 mmol) of N-(4-diphenylaminophenyl)-N-phenylamine, 57.5 mg (0.1 mmol) of bis(dibenzylidene acetone) palladium and 335 mg (3.5 mmol) of sodium tert-butoxide were mixed in a three-neck flask. Nitrogen was substituted for air inside of the three-neck flask. Then, 3.5 ml of dehydrated toluene was added in the mixture in the three-neck flask, and degassed for about 3 minutes. Subsequently, 0.4 ml of tri-tert-butyl phosphine (a 10 wt % hexane solution) was added to the mixture and the content was mixed by lightly shaking the container up and down. The content was stirred further for 10 minutes while being irradiated and heated at 80° C. with 200 W of microwave. After the reaction, saturated saline was added and a product was extracted with 100 ml of ethyl acetate. Further, magnesium sulfate was added to the product to remove moisture, and then the magnesium sulfate was filtered to be removed. The filtrate was concentrated, and a target matter was taken out by a silica gel column using a solvent containing ethyl acetate and hexane with a ratio of 1:1. Hexane was added to the thus-obtained solution and the resultant was heated to be recrystallized. Consequently, 650 mg (the yield: 65%) of a cream-colored powder was obtained. The NMR data is shown below. The 1H-NMR (300 MHz, DMSO-d); δ=6.89-7.05 (m, 13H), 7.21-7.28 (m, 9H), 7.32-7.43 (m, 3H), 7.50-7.69 (m, 5H), 8.02 (s, 1H), 8.14 (d, j=7.2, 1H). Also, a chart of 1H-NMR is shown in FIG. 13. Also, a chart of an enlarged portion of FIG. 13 in the range of 6.0 ppm and 9.0 ppm is shown in FIG. 14.

Provenance & Evidence