2-(Tri-n-butylstannyl)thiophene → HCID 178511111, compound

Participants

Reaction Steps

Dibromotetraphenylenedimalononitrile 10 (180 mg, 0.187 mmol), 2-tributylstannylthiophene (168 mg, 0.449 mmol), and Pd(PPh3)4 (15 mg) in anhydrous toluene (8.0 mL) were heated overnight at 110° C. under nitrogen. The reaction mixture was cooled to room temperature and concentrated to dryness. The crude product was purified by column chromatography on silica gel (CHCl3/hexanes (7:3)) to give 2,8-dithien-2-yl-tetraphenylenedimalononitrile (10B) as a yellow solid (0.114 g, 70% yield). 1H NMR (CDCl3): δ 0.88-1.66 (m, 46H), 2.10 (t, 4H), 7.13 (t, 2H) 7.35 (d, 2H, J=4.5 Hz), 7.44 (d, 2H, J=3.5 Hz), 7.51 (s, 2H), 7.75 (d, 2H, J=8.0 Hz), 8.69 (s, 2H), 8.78 (s, 2H) ppm; m.p: 280-281° C.; MS(MALDI-TOF) m/z (M+): 870.8; and Elemental Analysis: C, 79.80; H, 7.74.

Provenance & Evidence