bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane synthesis
- Product Name:bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane
- CAS Number:848464-60-8
- Molecular formula:C48H34N2Si
- Molecular Weight:666.88
Yield:848464-60-8 37.2%
Reaction Conditions:
with 18-crown-6 ether;copper;potassium carbonate in 1,2-dichloro-benzene at 180; for 72 h;Inert atmosphere;Ullmann Condensation;
Steps:
Bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane (p-CzSi).
Compound p-CzSi was prepared according toprocedure from the literature [10, 11]. Compound 1(0.71 g, 1.43 mmol), carbazole (0.61 g, 3.65 mmol), copper powder (0.40 g, 6.3 mmol), and 18-crown-6(0.07 g, 0.26 mmol) and K2CO3 (1.57 g, 11.4 mmol)were dissolved in 3 mL of anhydrous o-dichlorobenzeneunder nitrogen atmosphere. The reaction mixture was refluxed for 72 h at 180°C. After cooling to room temperature, the mixture was diluted in dichloromethane and filtered through silica gel. The filtrate was evaporated under reduced pressure to give crude product, which was then purified by column chromatography to give white powdery product (0.355 g, 37.2%). 1H NMR (CDCl3, 600 MHz):δ (ppm) = 8.18 (d, 4H, J = 7.7 Hz), 7.88-7.95 (m,4H), 7.73-7.79 (m, 4H), 7.70 (d, 4H, J = 8.25 Hz),7.50-7.59 (m, 10H), 7.41-7.49 (m, 4H), 7.30-7.37(m, 4H). 13C NMR (CDCl3, 100MHz): δ (ppm) =140.59, 139.26, 137.92, 136.46, 133.58, 133.20, 130.05,128.21, 126.28, 125.97, 123.58, 120.34, 120.14, 109.91.MALDI-TOF MS (m/z): calcd. for C48H34N2Si666.25, found 666.986.
References:
Ho, Kar Wei;Ariffin [Russian Journal of Physical Chemistry,2016,vol. 90,# 13,p. 2590 - 2599]
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