反应 #1904048

反应方程式

9,9-didecyl-2,7-diiodofluorene

diphenylamine

→

(9,9-Didecyl-7-iodofluoren-2-yl)diphenylamine

(9,9-Didecyl-7-iodofluoren-2-yl)-diphenylamine

反应条件

后处理

1. 1
   其他condensation
2. 2
   其他The orange-brown oil was further purified by column chromatography on silica gel using first (70:30) hexanes/CH2Cl2

实验过程

9,9-Didecyl-7-iodofluoren-2-yl)diphenylamine (15) (0.49 g, 0.66 mmol) was subjected to similar Ullmann condensation reaction with 9,9-didecyl-2,7-bis(phenylamino)fluorene (0.17 g, 0.27 mmol) to yield the desired product. (9,9-Didecyl-7-iodofluoren-2-yl)diphenylamine (15) was prepared by reaction of 9,9-didecyl-2,7-diiodofluorene (reported in Example 7) with one equivalent of diphenylamine. TLC analysis (60:40 hexanes/CH2Cl2) indicated condensation was complete after 4 days. The orange-brown oil was further purified by column chromatography on silica gel using first (70:30) hexanes/CH2Cl2 followed by (80:20) hexanes/CH2Cl2 resulting in 0.42 g of yellow solid (85% yd). Anal. Calcd for C135H174N4: C, 87.51%, H, 9.46%, N, 3.02%. Found: C, 87.37; H, 9.53%, N, 3.02%. 1H NMR (300 MHz. C6D) δ: 7.09 (d, 2H), 7.04 (s, 1H), 7.0 (dd, 5H), 6.93 (s, 1H), 6.85 (t, 6H), 6.73 (t, 6H), 6.53 (m, 3H), 1.33 (m, 4H), 0.87 (bd, 28H), 0.52 (bt, 10H). 13C NMR (300 MHz, C6D6) δ: 152.4, 148.5. 147.0, 136.6, 129.4, 124.2, 123.9, 120.2, 119.6, 119.1, 55.2, 40.3, 32.2, 30.4, 30.0, 29.8, 29.7, 29.6, 24.4, 22.9, 14.2. FT-IR (KBr, cm1): 3036 (vArCH), 2926; 2854 (valCH), 1593 (vArC═C).

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