Reaktion #360674

Reaktionsgleichung

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

Lösungsmittel

1,2-dichlorobenzene

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas charged into an argon-
2. 2
   workup.ADDITIONfilled 200 mL flask
3. 3
   Sonstigefitted with a condenser
4. 4
   TemperaturThe mixture was heated
5. 5
   Temperaturunder reflux in an argon atmosphere for 24 h
6. 6
   Filtrationfiltered
7. 7
   SonstigeA viscous liquid, obtained
8. 8
   Sonstigeafter removal of solvent
9. 9
   Sonstigeon a rotary evaporator
10. 10
    workup.ADDITIONwas added to 400 mL of methanol with vigorous stirring
11. 11
    FiltrationThe precipitated yellow solid was filtered
12. 12
    Waschenwashed several times with water and methanol
13. 13
    workup.DISSOLUTIONdissolved in 400 mL of hexane
14. 14
    Temperaturby heating
15. 15
    Filtrationfiltered
16. 16
    Sonstigeto remove the insoluble impurities
17. 17
    EinengenThe filtrate was concentrated to about 50 mL
18. 18
    Temperaturto cool down to room temperature
19. 19
    Temperaturchilled at 0° C. overnight
20. 20
    FiltrationThe crystallized yellow product was filtered
21. 21
    Waschenwashed with a small amount of hexane
22. 22
    Sonstigedried

Vorschrift

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.

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