反应 #360674

反应方程式

1-iodo-4-octylbenzene

5,11-dihydridoindolo[3,2-b]carbazole

18-crown-6

K2CO3

→

5,11-bis(4-octylphenyl)indolo[3,2-b]carbazole

溶剂

1,2-dichlorobenzene

tetrahydrofuran

反应条件

后处理

1. 1
   workup.ADDITIONwas charged into an argon-
2. 2
   workup.ADDITIONfilled 200 mL flask
3. 3
   其他fitted with a condenser
4. 4
   温度The mixture was heated
5. 5
   温度under reflux in an argon atmosphere for 24 h
6. 6
   过滤filtered
7. 7
   其他A viscous liquid, obtained
8. 8
   其他after removal of solvent
9. 9
   其他on a rotary evaporator
10. 10
    workup.ADDITIONwas added to 400 mL of methanol with vigorous stirring
11. 11
    过滤The precipitated yellow solid was filtered
12. 12
    洗涤washed several times with water and methanol
13. 13
    workup.DISSOLUTIONdissolved in 400 mL of hexane
14. 14
    温度by heating
15. 15
    过滤filtered
16. 16
    其他to remove the insoluble impurities
17. 17
    浓缩The filtrate was concentrated to about 50 mL
18. 18
    温度to cool down to room temperature
19. 19
    温度chilled at 0° C. overnight
20. 20
    过滤The crystallized yellow product was filtered
21. 21
    洗涤washed with a small amount of hexane
22. 22
    其他dried

实验过程

A mixture of 1-iodo-4-octylbenzene (16.09 g, 35.1 mmol, 69% of purity) as prepared above, 5,11-dihydridoindolo[3,2-b]carbazole (3.00 g, 11.7 mmol), 18-crown-6 (0.62 g, 2.34 mmol), K2CO3 (12.94 g, 93.6 mmol), copper (2.97 g, 46.8 mmol), and 1,2-dichlorobenzene (50 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 tetrahydrofuran, and filtered. A viscous liquid, obtained after removal of solvent on a rotary evaporator, was added to 400 mL of methanol with vigorous stirring. The precipitated yellow solid was filtered, washed several times with water and methanol, dissolved in 400 mL of hexane by heating, and filtered to remove the insoluble impurities. The filtrate was concentrated to about 50 mL and allowed to cool down to room temperature, and then chilled at 0° C. overnight. The crystallized yellow product was filtered, washed with a small amount of hexane, and dried to yield 5.32 g of 5,11-bis(4-octylphenyl)indolo[3,2-b]carbazole, compound (2), which was subject to train sublimation to obtain electrically pure compound for OTFT fabrication. DSC showed a melting point at 131° C. on first heating. 1H NMR (CDCl3): δ 8.12 (d, J=7.6 Hz, 2H), 8.05 (s, 2H), 7.58 (d, J=8.3 Hz, 4H), 7.47 (d, J=8.3 Hz, 4H), 7.39-7.40 (m, 4H), 7.19-7.21 (m, 2H), 2.78 (t, J=7.8 Hz, 4H), 1.78 (pent, J=7.4 Hz, 4H), 1.30-1.50 (m, 20H), 0.92 (m, 6H); IR (NaCl): 3047, 2956, 2923, 2852, 1517, 1451, 1324, 1236, 842, 731 cm−1.

来源