反应详情

Mix 2.80 g (8.77 mmol) of 3,6-diphenylcarbazole, 22.18 g (87.7 mmol) of 1-bromo-3-iodine benzene, 0.279 g of copper powder, and 4.85 g of potassium carbonate; heat the mixture at 190° C. for nine hours in nitrogen atmosphere followed by cooling down to room temperature; next, dilute the mixture with methylene chloride followed by water-washing and drying to obtain pale brown liquid; furthermore, refine the resultant with silica gel column chromatography using a liquid mixture of methylene chloride and hexane as an eluting solution to obtain 3.59 g of 9-(3-bromophenyl)-3,6-diphenyl carbazole; add 3.20 g (6.75 mmol) of the thus obtained 9-(3-bromophenyl)-3,6-diphenyl carbazole, 1.54 g (10.1 mmol) of 3-methoxyphenyl boronic acid, and 0.124 g of tetrakis(triphenyl phosphine)palladium to a liquid mixture of 30 ml of toluene and 10 ml of ethanol; add an aqueous solution in which 37.3 g of sodium carbonate is dissolved in 90 ml of distilled water to the mixture; reflux the mixture for nine hours while heating in nitrogen atmosphere followed by cooling down to room temperature; next, dilute the mixture with methylene chloride; remove insoluble matters by filtration; wash the organic layer with water for separation; distill away the solvent under a reduced pressure; and furthermore, refine the resultant with silica gel column chromatography using a liquid mixture of methylene chloride and hexane as an eluting solution to obtain 2.89 g of [3′-(3,6-diphenylcarbazole-9-yl)biphenyl-3-yloxy]methane; and prepare 8-[3′-(3,6-diphenylcarbazole-9-yl)biphenyl-3-yloxy]octane-1-thiol (C-4) (hereinafter referred to as carbazole derivative 7) represented by the chemical structure 13 in the same manner as in preparation of Carbazole Derivative 1 except that the thus obtained [3′-(3,6-diphenylcarbazole-9-yl)biphenyl-3-yloxy]methane is used instead of 3,6-bis(5-methylthiophene-2-yl)-9-(4-methoxyphenyl)carbazole (B-2).

1. temperaturereflux the mixture for nine hours
2. temperaturewhile heating in nitrogen atmosphere
3. filtrationremove insoluble matters by filtration
4. washwash the organic layer with water
5. customfor separation
6. distillationdistill away the solvent under a reduced pressure
7. additiona liquid mixture of methylene chloride and hexane as an eluting solution