反应详情

To 11-(2-ethylhexyl)-11H-benzo[a]carbazole (1.65 g; 5.00 mmol) in CH2Cl2 (15 mL) are added 2,4,6-trimethylbenzoyl chloride (0.92 g; 5.11 mmol) and AlCl3 (0.70 g; 5.25 mmol) at 0° C. After stirring at room temperature for 1 hour, AlCl3 (0.70 g; 5.30 mmol) is added at 0° C. and adipoyl chloride (0.43 g; 2.33 mmol) is added dropwise, and then the mixture is stirred at room temperature overnight. The reaction mixture is poured into ice-water, and the crude product is extracted twice with CH2Cl2. The combined organic layer is washed with water and brine, dried over MgSO4, and concentrated to give a green solid. The crude product is purified by column chromatography on silica gel eluting with a mixed solvent of CH2Cl2 and n-hexane (1:1) to give a beige solid (0.85 g; 34.4%). The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 0.82 (t, 6H), 0.89 (t, 6H), 1.17-1.42 (m, 16H), 1.93 (br, 4H), 2.21 (s, 12H), 2.26 (m, 2H), 2.40 (s, 6H), 3.18 (br, 4H), 4.69 (m, 4H), 6.97 (s, 4H), 7.54 (d, 2H), 7.69-7.78 (m, 4H), 8.08 (s, 2H), 8.39 (s, 2H), 8.61 (br, 4H), 9.53 (d, 2H).

1. stirringthe mixture is stirred at room temperature overnight
2. extractionthe crude product is extracted twice with CH2Cl2
3. washThe combined organic layer is washed with water and brine
4. dry with materialdried over MgSO4
5. concentrationconcentrated
6. customto give a green solid
7. customThe crude product is purified by column chromatography on silica gel eluting with a mixed solvent of CH2Cl2 and n-hexane (1:1)
8. customto give a beige solid (0.85 g; 34.4%)