Chloranil → HCID 58289108, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of trans-6,13-Bis(phenethylthio)-6,13-dihydropentacene (0.97 g, 1.76 mmol), tetrachloro-1,4-benzoquinone (0.87 g, 3.52 mmol) and potassium carbonate (2.43 g, 17.6 mmol) in dry benzene (170 mL) was stirred at 60° C. for 48 h under an argon atmosphere in the dark. After cooling to RT, the reaction mixture was filtered and washed with CH2Cl2. After evaporation of the filtrate, the solid residue was triturated with n-hexanes, filtered, and washed with hexane. After evaporation of the filtrate, the solid residue was passed through short column of n-Al2O3 eluted with CH2Cl2 and the deep blue band was collected. The solvent was evaporated to give pure 6,13-bis(phenethylthio)pentacene as deep blue solids in 72% yield (0.70 g). 1H NMR (500 MHz, CDCl3): δ 9.63 (s, 4H), 8.00 (m, 4H), 7.40 (m, 4H), 7.19 (m, 6H), 7.06 (d, 4H, J=7.08 Hz), 3.32 (t, 4H, J=7.56 Hz), 2.86 (t, 4H, J=7.56 Hz). 13C NMR (125.68 MHz, CDCl3): δ 140.91, 140.20, 132.83, 132.19, 128.88, 128.67, 128.52, 127.01, 126.49, 126.07, 38.97, 36.46. LDI-MS m/z: 550 [M+], UV-vis λmax(nm): 618, 571, 530.

Provenance & Evidence