2,4,6-tris(3-(carbazol-9-yl)phenyl)-1,3,5-triazine synthesis

Yield:890148-68-2 79%

Reaction Conditions:

with tri-tert-butyl phosphine;palladium dichloride;sodium t-butanolate in o-xylene at 120; for 17 h;Inert atmosphere;

Steps:

Synthesis of TCPZ

A mixture of TBrPZ (0.979 g, 1.8 mmol), carbazole (1.05 g, 6.3 mmol), PdCl2 (28.7 mg, 0.162 mmol), tris(tertbutyl) phosphine (131 mg, 0.648 mmol), and sodium tertbutoxide (0.778 g, 8.1 mmol) in anhydrous o-xylene (100 mL) was stirred at 120 C for 17 h under nitrogen atmosphere. After cooling to room temperature, the mixture was poured into water and then extracted with chloroform. The combined organic phase was washed with brine and dried over MgSO4. The subjection of the crude mixture to silica gel chromatography (chloroform/n-hexane = 2/1) afforded TCPZ (1.14 g, 79%) as white powders. 1H NMR (500 MHz, CDCl3): d (ppm) 8.93 (t, J = 2.0 Hz, 3H), 8.74 (d, J = 8.0 Hz, 3H), 8.15 (d, J = 8.0 Hz, 6H), 7.78 (d, J = 8.0 Hz, 3H), 7.73 (t, J = 8.0 Hz, 3H), 7.42 (d, J = 8.0 Hz, 6H), 7.33 (t, J = 7.0 Hz, 6H), 7.28 (t, J = 7.0 Hz, 6H). 13C NMR (500 MHz, CDCl3): d (ppm) 171.26, 140.76, 138.26, 137.84, 131.30, 130.30, 128.06, 127.60, 126.08, 123.42, 120.32, 120.11, 109.60. MS (EI): m/z 806 [M+H+] (calcd m/z 804.94). Anal. Calc. for C57H36N6 (%): C, 85.05; H, 4.51; N, 10.44. Found: C, 85.10; H, 4.70; N, 10.14.

References:

Su, Shi-Jian;Cai, Chao;Takamatsu, Junichi;Kido, Junji [Organic electronics,2012,vol. 13,# 10,p. 1937 - 1947,11]