4-Bromotetraphene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 14 g (7.9 mmol) of tri-o-tolylphosphine and then 300 mg (1.3 mmol) of palladium(II) acetate are added to a well-stirred suspension of 50 g (333 mmol) of 4-formylphenylboronic acid, 81 g (266 mmol) of 4-bromobenz[a]anthracene and 118 g (558 mmol) of tripotassium phosphate in a mixture of 500 ml of toluene, 500 ml of dioxane and 400 ml of water, and the mixture is subsequently heated under reflux for 16 h. After cooling, the precipitated solid is filtered off with suction, washed three times with 50 ml of toluene, three times with 50 ml of ethanol:water (1:1, v:v), three times with 100 ml of ethanol and finally dried. Yield: 49.7 g (149 mmol), 56%. the mixture is subsequently heated under reflux for 16 h After cooling the precipitated solid is filtered off with suction washed three times with 50 ml of toluene, three times with 50 ml of ethanol:water (1:1, v:v), three times with 100 ml of ethanol finally dried

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 190 μl (1 mmol) of chlorodi-tert-butylphosphine and then 112 mg (0.5 mmol) of palladium(II) acetate are added to a suspension of 15.4 g (50 mmol) of 4-bromobenz[a]anthracene, 10.2 g (60 mmol) of diphenylamine and 7.7 g (80 mmol) of sodium tert-butoxide in 500 ml of toluene, and the mixture is subsequently heated under reflux for 5 h. After the mixture has been cooled to 60° C., 500 ml of water are added, the organic phase is separated off, filtered through silica gel, evaporated virtually to dryness at 80° C. in vacuo, and 300 ml of ethanol are then added. After cooling, the solid is filtered off with suction. Recrystallisation five times from dioxane (about 8 ml/g); sublimation (p=5×10−5 mbar, T=280° C.). Yield: 12.7 g (32 mmol), 64.1%, purity 99.9% (HPLC), Tg=74.7° C. the mixture is subsequently heated under reflux for 5 h the organic phase is separated off filtered through silica gel evaporated virtually to dryness at 80° C. in vacuo, and 300 ml of ethanol are then added After cooling the solid is filtered off with suction Recrystallisation five times from dioxane (about 8 ml/g) sublimation (p=5×10−5 mbar, T=280° C.)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 190 μl (1 mmol) of chlorodi-tert-butylphosphine and then 112 mg (0.5 mmol) of palladium(II) acetate are added to a suspension of 15.4 g (50 mmol) of 4-bromobenz[a]anthracene, 10.2 g (60 mmol) of diphenylamine and 7.7 g (80 mmol) of sodium tert-butoxide in 500 ml of toluene, and the mixture is subsequently heated under reflux for 5 h. After the mixture has been cooled to 60° C., 500 ml of water are added, the organic phase is separated off, filtered through silica gel, evaporated virtually to dryness at 80° C. in vacuo, and 300 ml of ethanol are then added. After cooling, the solid is filtered off with suction. Recrystallisation five times from dioxane (about 8 ml/g); sublimation (p=5×10−5 mbar, T=280° C.). Yield: 12.7 g (32 mmol), 64.1%, purity 99.9% (HPLC), Tg=74.7° C. the mixture is subsequently heated under reflux for 5 h the organic phase is separated off filtered through silica gel evaporated virtually to dryness at 80° C. in vacuo, and 300 ml of ethanol are then added After cooling the solid is filtered off with suction Recrystallisation five times from dioxane (about 8 ml/g) sublimation (p=5×10−5 mbar, T=280° C.)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Preparation analogous to Example 7. 9-Bromo-10-(2-naphthyl)anthracene is replaced by 15.4 g (50 mmol) of 4-bromobenz[a]anthracene. Recrystallisation four times from o-dichlorobenzene (about 15 ml/g); sublimation (p=5×10−5 mbar, T=320° C.). Yield: 16.8 g (37 mmol), 74.0%, purity 99.9% (HPLC), Tg=130.3° C. Preparation analogous to Example 7 Recrystallisation four times from o-dichlorobenzene (about 15 ml/g) sublimation (p=5×10−5 mbar, T=320° C.)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 190 μl (1 mmol) of chloro-di-tert-butylphosphine and then 112 mg (0.5 mmol) of palladium(II) acetate are added to a suspension of 15.4 g (50 mmol) of 4-bromobenz[a]anthracene, 11.8 g (60 mmol) of bis(3-methylphenyl)amine and 7.7 g (80 mmol) of sodium tert-butoxide in 500 ml of toluene, and the mixture is subsequently heated under reflux for 5 h. After the mixture has been cooled to 60° C., 500 ml of water are added, the organic phase is separated off, filtered through silica gel, evaporated virtually to dryness at 80° C. in vacuo, and 300 ml of ethanol are then added. After cooling, the solid is filtered off with suction. Recrystallisation five times from dioxane (about 8 ml/g); sublimation (p=5×10−5 mbar, T=280° C.). Yield: 11.9 g (28 mmol), 56.1%, purity 99.9% (HPLC). the mixture is subsequently heated under reflux for 5 h the organic phase is separated off filtered through silica gel evaporated virtually to dryness at 80° C. in vacuo, and 300 ml of ethanol are then added After cooling the solid is filtered off with suction Recrystallisation five times from dioxane (about 8 ml/g) sublimation (p=5×10−5 mbar, T=280° C.)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 14 g (7.9 mmol) of tri-o-tolylphosphine and then 300 mg (1.3 mmol) of palladium(II) acetate are added to a well-stirred suspension of 50 g (333 mmol) of 4-formylphenylboronic acid, 81 g (266 mmol) of 4-bromobenz[a]anthracene and 118 g (558 mmol) of tripotassium phosphate in a mixture of 500 ml of toluene, 500 ml of dioxane and 400 ml of water, and the mixture is subsequently heated under reflux for 16 h. After cooling, the precipitated solid is filtered off with suction, washed three times with 50 ml of toluene, three times with 50 ml of ethanol:water (1:1, v:v), three times with 100 ml of ethanol and finally dried. Yield: 49.7 g (149 mmol), 56%. the mixture is subsequently heated under reflux for 16 h After cooling the precipitated solid is filtered off with suction washed three times with 50 ml of toluene, three times with 50 ml of ethanol:water (1:1, v:v), three times with 100 ml of ethanol finally dried

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 190 μl (1 mmol) of chlorodi-tert-butylphosphine and then 112 mg (0.5 mmol) of palladium(II) acetate are added to a suspension of 15.4 g (50 mmol) of 4-bromobenz[a]anthracene, 10.2 g (60 mmol) of diphenylamine and 7.7 g (80 mmol) of sodium tert-butoxide in 500 ml of toluene, and the mixture is subsequently heated under reflux for 5 h. After the mixture has been cooled to 60° C., 500 ml of water are added, the organic phase is separated off, filtered through silica gel, evaporated virtually to dryness at 80° C. in vacuo, and 300 ml of ethanol are then added. After cooling, the solid is filtered off with suction. Recrystallisation five times from dioxane (about 8 ml/g); sublimation (p=5×10−5 mbar, T=280° C.). Yield: 12.7 g (32 mmol), 64.1%, purity 99.9% (HPLC), Tg=74.7° C. the mixture is subsequently heated under reflux for 5 h the organic phase is separated off filtered through silica gel evaporated virtually to dryness at 80° C. in vacuo, and 300 ml of ethanol are then added After cooling the solid is filtered off with suction Recrystallisation five times from dioxane (about 8 ml/g) sublimation (p=5×10−5 mbar, T=280° C.)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Preparation analogous to Example 7. 9-Bromo-10-(2-naphthyl)anthracene is replaced by 15.4 g (50 mmol) of 4-bromobenz[a]anthracene. Recrystallisation four times from o-dichlorobenzene (about 15 ml/g); sublimation (p=5×10−5 mbar, T=320° C.). Yield: 16.8 g (37 mmol), 74.0%, purity 99.9% (HPLC), Tg=130.3° C. Preparation analogous to Example 7 Recrystallisation four times from o-dichlorobenzene (about 15 ml/g) sublimation (p=5×10−5 mbar, T=320° C.)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 190 μl (1 mmol) of chloro-di-tert-butylphosphine and then 112 mg (0.5 mmol) of palladium(II) acetate are added to a suspension of 15.4 g (50 mmol) of 4-bromobenz[a]anthracene, 11.8 g (60 mmol) of bis(3-methylphenyl)amine and 7.7 g (80 mmol) of sodium tert-butoxide in 500 ml of toluene, and the mixture is subsequently heated under reflux for 5 h. After the mixture has been cooled to 60° C., 500 ml of water are added, the organic phase is separated off, filtered through silica gel, evaporated virtually to dryness at 80° C. in vacuo, and 300 ml of ethanol are then added. After cooling, the solid is filtered off with suction. Recrystallisation five times from dioxane (about 8 ml/g); sublimation (p=5×10−5 mbar, T=280° C.). Yield: 11.9 g (28 mmol), 56.1%, purity 99.9% (HPLC). the mixture is subsequently heated under reflux for 5 h the organic phase is separated off filtered through silica gel evaporated virtually to dryness at 80° C. in vacuo, and 300 ml of ethanol are then added After cooling the solid is filtered off with suction Recrystallisation five times from dioxane (about 8 ml/g) sublimation (p=5×10−5 mbar, T=280° C.)