تفاعل #360674

معادلة التفاعل

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

المذيبات

1,2-dichlorobenzene

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas charged into an argon-
2. 2
   workup.ADDITIONfilled 200 mL flask
3. 3
   أخرىfitted with a condenser
4. 4
   درجة الحرارةThe mixture was heated
5. 5
   درجة الحرارةunder reflux in an argon atmosphere for 24 h
6. 6
   ترشيحfiltered
7. 7
   أخرىA viscous liquid, obtained
8. 8
   أخرىafter removal of solvent
9. 9
   أخرىon a rotary evaporator
10. 10
    workup.ADDITIONwas added to 400 mL of methanol with vigorous stirring
11. 11
    ترشيحThe precipitated yellow solid was filtered
12. 12
    غسيلwashed several times with water and methanol
13. 13
    workup.DISSOLUTIONdissolved in 400 mL of hexane
14. 14
    درجة الحرارةby heating
15. 15
    ترشيحfiltered
16. 16
    أخرىto remove the insoluble impurities
17. 17
    تركيزThe filtrate was concentrated to about 50 mL
18. 18
    درجة الحرارةto cool down to room temperature
19. 19
    درجة الحرارةchilled at 0° C. overnight
20. 20
    ترشيحThe crystallized yellow product was filtered
21. 21
    غسيلwashed with a small amount of hexane
22. 22
    أخرىdried

الإجراء التجريبي

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.

المصدر