Iodine → 5,6-Dioctylnaphtho[2,1-b:3,4-b']dithiophene

反応式

[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:11]([C:12]3[CH:16]=[CH:15][S:14][CH:13]=3)=[CH:10][C:9]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:8]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:7]=2)=[CH:2]1.II>C1(C)C=CC=CC=1.[Hg]>[CH2:17]([C:9]1[CH:10]=[C:11]2[C:12]3[CH:16]=[CH:15][S:14][C:13]=3[C:2]3[S:1][CH:5]=[CH:4][C:3]=3[C:6]2=[CH:7][C:8]=1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

参加物

実験手順

In a quartz tube was added a solution of 4,5-bis(3-thienyl)-1,2-dioctylbenzene (0.5 g, 1.1 mmol) and iodine (30 mg) in toluene (500 mL). The system was then irradiated by a 400 W mercury lamp equipped with an efficient cooling system for 16 hours under magnetic stirring and air bubbling. The reaction mixture was washed with a saturated aqueous solution of Na2S2O3, dried over MgSO4 and concentrated. The residue was purified by flash chromatography on silica gel (hexane as eluent), and a white solid was obtained (0.33 g, yield: 65%). mp: 62.2-63.1° C. 1H NMR (400 MHz, CDCl3) δ 8.11 (s, 2H), 7.97 (d, 2H), J=5.34 Hz), 7.47 (d, 2H, J=5.30), 2.86 (t, 4H, J=7.76 Hz), 1.74 (m, 4H), 1.32-1.50 (m, 20H), 0.92 (t, 6H), J=6.80 Hz). 13C NMR (400 MHz, CDCl3) δ 139.22, 134.12, 131.25, 126.09, 124.04, 123.34, 122.74, 33.14, 31.29, 31.52, 29.86, 29.58, 29.34, 22.70, 14.14. MS: m/z=464.4 [M]+ (Calcd.: 464.2).