Dimethylformamide → HCID 66822907, compound
Reaction equation
[CH2:1]([N:7]1[C:14]([C:15]2[S:16][C:17](Br)=[CH:18][CH:19]=2)=[C:13]2[C:9](=[C:10]([C:28]3[S:29][C:30](Br)=[CH:31][CH:32]=3)[N:11]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:12]2=[O:21])[C:8]1=[O:34])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Cu][C:36]#[N:37].[CH3:38][N:39](C=O)C>>[CH2:1]([N:7]1[C:14]([C:15]2[S:16][C:17]([C:38]#[N:39])=[CH:18][CH:19]=2)=[C:13]2[C:9](=[C:10]([C:28]3[S:29][C:30]([C:36]#[N:37])=[CH:31][CH:32]=3)[N:11]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:12]2=[O:21])[C:8]1=[O:34])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]Participants
4
Conditions
- Temperature
- 130 °C
Procedure
The synthesis of 2,5-di-n-hexyl-3,6-bis(5-bromo-thiophen-2-yl)pyrrolo[3,4-c]-pyrrole-1,4-dione is done in analogy to Zhou et al., Macromolecules 43 (2010) 821-826. 2,5-Di-n-hexyl-3,6-bis(5-bromo-thiophen-2-yl)pyrrolo[3,4-c]-pyrrole-1,4-dione (237 mg, 0.378 mmol) and copper(I)-cyanide (1.50 g, 17.0 mmol) are placed in a 25 mL-flask under argon. Dry DMF (10 mL) is added and the mixture is stirred at 130° C. for 4 h. The solvent is removed under reduced pressure and the residual solid is extracted with chloroform (250 mL). After removing the solvent the crude product is purified by column chromatography (dichloromethane). A violet solid is obtained (52 mg, 27%).