1-Bromopyrene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixed solution of 45.0 g of 1-bromopyrene, 21.7 g of 4-methylphenylboronic acid, 34.0 g of tripotassium phosphate, 10.3 g of tetrabutylammonium bromide, 0.71 g of palladium acetate and 1.6 L of dimethylformamide was heated with stirring under a nitrogen gas flow at 120° C. for 5 hours. After cooling to room temperature, 1.6 L of water was injected, followed by stirring at room temperature for 0.5 hours. The precipitated solid was collected by filtration and then washed twice with 200 ml of water. The resultant solid was dissolved in 500 ml of dichloromethane, dried over magnesium sulfate, evaporated and then filtered using Celite. The filtrate was evaporated and the residue was washed twice with 200 ml of methanol. The precipitated solid was collected by filtration and then vacuum-dried to obtain 40.0 g of 1-(4-methylphenyl)pyrene. After cooling to room temperature by stirring at room temperature for 0.5 hours The precipitated solid was collected by filtration washed twice with 200 ml of water The resultant solid was dissolved in 500 ml of dichloromethane dried over magnesium sulfate evaporated filtered The filtrate was evaporated the residue was washed twice with 200 ml of methanol The precipitated solid was collected by filtration vacuum-dried

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixed solution of 7.0 g of 1-bromopyrene, 4.7 g of 2-naphthaleneboronic acid, 11.6 g of tripotassium phosphate, 1.8 g of tetrabutylammonium bromide, 0.11 g of palladium acetate and 248 ml of dimethylformamide was heated with stirring under a nitrogen gas flow at 130° C. for 5 hours. After cooling the solution to room temperature, 300 ml of water was injected, followed by stirring at room temperature for 0.5 hours. The precipitated solid was collected by filtration and then washed twice with 100 ml of water. The resultant solid was dissolved in 200 ml of dichloromethane, dried over magnesium sulfate, evaporated and then filtered using Celite. The filtrate was evaporated and the residue was washed twice with 100 ml of methanol, and then the precipitated solid was collected by filtration. The solid was vacuum-dried to obtain 7.5 g of 1-(2-naphthyl)pyrene. After cooling the solution to room temperature by stirring at room temperature for 0.5 hours The precipitated solid was collected by filtration washed twice with 100 ml of water The resultant solid was dissolved in 200 ml of dichloromethane dried over magnesium sulfate evaporated filtered The filtrate was evaporated the residue was washed twice with 100 ml of methanol the precipitated solid was collected by filtration The solid was vacuum-dried

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixed solution of 7.0 g of 1-bromopyrene, 4.7 g of 2-naphthaleneboronic acid, 11.6 g of tripotassium phosphate, 1.8 g of tetrabutylammonium bromide, 0.11 g of palladium acetate and 248 ml of dimethylformamide was heated with stirring under a nitrogen gas flow at 130° C. for 5 hours. After cooling the solution to room temperature, 300 ml of water was injected, followed by stirring at room temperature for 0.5 hours. The precipitated solid was collected by filtration and then washed twice with 100 ml of water. The resultant solid was dissolved in 200 ml of dichloromethane, dried over magnesium sulfate, evaporated and then filtered using Celite. The filtrate was evaporated and the residue was washed twice with 100 ml of methanol, and then the precipitated solid was collected by filtration. The solid was vacuum-dried to obtain 7.5 g of 1-(2-naphthyl)pyrene. After cooling the solution to room temperature by stirring at room temperature for 0.5 hours The precipitated solid was collected by filtration washed twice with 100 ml of water The resultant solid was dissolved in 200 ml of dichloromethane dried over magnesium sulfate evaporated filtered The filtrate was evaporated the residue was washed twice with 100 ml of methanol the precipitated solid was collected by filtration The solid was vacuum-dried

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Bromopyrene (2.00 g, 7.12 mmol) was dissolved in anhydrous THF (150 ml) and anhydrous ether (150 ml). The light yellow solution was cooled to −78° C. in nitrogen. n-Butyllithium (4.9 ml, 7.83 mmol) was slowly dripped into the solution. At this time, the solution became murky. This mixture was kept at −78° C. for ten minutes, 0° C. for ten minutes, and then −78° C. for thirty minutes. Then, triisopropyl borate (4.93 ml, 21.36 mmol) was slowly dripped into the solution, and the mixture was kept at −78° C. for thirty minutes. Finally, the mixture underwent reaction at room temperature for 1.5 days. Next, water was added into the reaction mixture, and the resulting mixture was stirred vigorously for one hour. The water layer and the organic layer were separated, the water layer was then extracted by ethyl ether (2×25 ml), and the organic layer was water washed (2×50 ml). The combined organic solution was contact with MgSO4 to remove water, then filtered, and concentrated on a rotary evaporator to obtain a pyreneboronic acid solid product. This mixture was kept at −78° C. for ten minutes, 0° C. for ten minutes −78° C. for thirty minutes the mixture was kept at −78° C. for thirty minutes Finally, the mixture underwent reaction at room temperature for 1.5 days The water layer and the organic layer were separated the water layer was then extracted by ethyl ether (2×25 ml) washed (2×50 ml) to remove water filtered concentrated on a rotary evaporator

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Bromopyrene (2.00 g, 7.12 mmol) was dissolved in anhydrous THF (150 ml) and anhydrous ether (150 ml). The light yellow solution was cooled to −78° C. in nitrogen. n-Butyllithium (4.9 ml, 7.83 mmol) was slowly dripped into the solution. At this time, the solution became murky. This mixture was kept at −78° C. for ten minutes, 0° C. for ten minutes, and then −78° C. for thirty minutes. Then, triisopropyl borate (4.93 ml, 21.36 mmol) was slowly dripped into the solution, and the mixture was kept at −78° C. for thirty minutes. Finally, the mixture underwent reaction at room temperature for 1.5 days. Next, water was added into the reaction mixture, and the resulting mixture was stirred vigorously for one hour. The water layer and the organic layer were separated, the water layer was then extracted by ethyl ether (2×25 ml), and the organic layer was water washed (2×50 ml). The combined organic solution was contact with MgSO4 to remove water, then filtered, and concentrated on a rotary evaporator to obtain a pyreneboronic acid solid product. This mixture was kept at −78° C. for ten minutes, 0° C. for ten minutes −78° C. for thirty minutes the mixture was kept at −78° C. for thirty minutes Finally, the mixture underwent reaction at room temperature for 1.5 days The water layer and the organic layer were separated the water layer was then extracted by ethyl ether (2×25 ml) washed (2×50 ml) to remove water filtered concentrated on a rotary evaporator

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

Procedure: Under a dry nitrogen atmosphere, n-BuLi (10.6 mL, 1.6 M) in hexanes was added drop-wise to a cooled (−60° C.) solution of 1-bromopyrene (5.01 g, 0.018 mol) in THF/Et2O (1:1) (80 mL) and stirred for 2 hours at −60° C. The solution was cooled to −90° C. and a THF solution of SiCl4 (8.66 g, 0.051 mol) (10 mL) was added slowly and stirred for 24 hours at room temperature. The reaction mixture was evaporated to dryness, washed in Et2O (100 mL), and filtered to remove any unreacted 1-bromopyrene and LiBr. The filtrate was collected and evaporated to dryness to give a 48% yield of 1-trichlorosilylpyrene, a yellow powder. 1HNMR (CDCl3, ppm) 8.66 (d, J=9.3 Hz, 1H), 8.59 (d, J=8.1 Hz, 1H), 8.30 (m, 5H), 8.11 (m, 2H). 13C {1H}NMR (CDCl3, ppm) 136.18 (C), 135.85 (C), 133.13 (CH), 132.06 (C), 131.30 (C), 131.22 CH), 130.31 (CH), 127.96 (CH), 127.67 (CH), 127.61 (CH), 126.65 (CH), 125.61 (C), 125.01 (CH), and 124.39 (C). 29Si{1H} (CDCl3, ppm) −1.64 (s). The solution was cooled to −90° C. stirred for 24 hours at room temperature The reaction mixture was evaporated to dryness washed in Et2O (100 mL) filtered to remove any unreacted 1-bromopyrene and LiBr The filtrate was collected evaporated to dryness

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

Procedure: 1-Bromopyrene (10 mmol), C6H5NH2 (12 mmol), Pd(dba)2 (0.20 mmol), P(t-Bu)3 (0.20-0.30 mmol) and sodium t-butoxide (1.44 g, 15 mmol) were charged in a two-necked flask under a nitrogen atmosphere. Toluene (25 ml) was added and the resulting violet solution was stirred at room temperature for 8 hours. During this period the contents of the flask became a pale yellow fluorescent solution. The reaction was quenched with water (30 ml) and the organic layer was taken into 100 ml diethyl ether, washed with brine solution, and dried over MgSO4. Evaporation of the solvent under vacuum resulted in a yellow solid that was adsorbed in silica gel and purified by column chromatography using dichloromethane/hexane (1:1) as eluant to produce phenyl-pyren-1-yl-amine (89%). During this period the contents of the flask became The reaction was quenched with water (30 ml) washed with brine solution dried over MgSO4 Evaporation of the solvent under vacuum resulted in a yellow solid purified by column chromatography

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

Procedure: 1-Bromopyrene (10 mmol), C6H5NH2 (12 mmol), Pd(dba)2 (0.20 mmol), P(t-Bu)3 (0.20-0.30 mmol) and sodium t-butoxide (1.44 g, 15 mmol) were charged in a two-necked flask under a nitrogen atmosphere. Toluene (25 ml) was added and the resulting violet solution was stirred at room temperature for 8 hours. During this period the contents of the flask became a pale yellow fluorescent solution. The reaction was quenched with water (30 ml) and the organic layer was taken into 100 ml diethyl ether, washed with brine solution, and dried over MgSO4. Evaporation of the solvent under vacuum resulted in a yellow solid that was adsorbed in silica gel and purified by column chromatography using dichloromethane/hexane (1:1) as eluant to produce phenyl-pyren-1-yl-amine (89%). During this period the contents of the flask became The reaction was quenched with water (30 ml) washed with brine solution dried over MgSO4 Evaporation of the solvent under vacuum resulted in a yellow solid purified by column chromatography

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

Procedure: 7.4 g of 4-(naphthalene-1-yl)phenyl boronic acid prepared by a well known method and 7.0 g of conventional 1-bromopyrene were dissolved in 80 ml of dimethoxyethane (DME). Subsequently, 0.58 g of tetrakistriphenylphosphine palladium and 40 ml of 2M-sodium carbonate aqueous solution were added therein, followed by argon displacement. After heating and refluxing over 8 hours, it was stood to cool and then an organic layer was extracted therefrom by toluene. The organic layer was washed by saturated salt water, followed by drying through anhydrous sodium sulfate, and then the organic solvent was removed by an evaporator. The residue was refined through a silica gel chromatography (a developing solvent: toluene) and then 10.0 g of 1-(4-naphthalene-1-yl-phenyl) pyrene was obtained. (yield: 99%) After heating refluxing over 8 hours to cool an organic layer was extracted The organic layer was washed by saturated salt water by drying through anhydrous sodium sulfate the organic solvent was removed by an evaporator

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

Procedure: 7.4 g of 4-(naphthalene-1-yl)phenyl boronic acid prepared by a well known method and 7.0 g of conventional 1-bromopyrene were dissolved in 80 ml of dimethoxyethane (DME). Subsequently, 0.58 g of tetrakistriphenylphosphine palladium and 40 ml of 2M-sodium carbonate aqueous solution were added therein, followed by argon displacement. After heating and refluxing over 8 hours, it was stood to cool and then an organic layer was extracted therefrom by toluene. The organic layer was washed by saturated salt water, followed by drying through anhydrous sodium sulfate, and then the organic solvent was removed by an evaporator. The residue was refined through a silica gel chromatography (a developing solvent: toluene) and then 10.0 g of 1-(4-naphthalene-1-yl-phenyl) pyrene was obtained. (yield: 99%) After heating refluxing over 8 hours to cool an organic layer was extracted The organic layer was washed by saturated salt water by drying through anhydrous sodium sulfate the organic solvent was removed by an evaporator