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Method for synthesizing 4,4'-bis(9h-carbazol-9-yl)biphenyls in one step

A technology of compounds and carbazoles, applied in the field of organic synthesis, can solve the problems of slow post-processing, complicated steps, long time consumption, etc., and achieve the effects of low cost, low price and simple reaction steps

Active Publication Date: 2022-04-01
CHANGZHOU INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The method of the invention not only solves the disadvantages of complicated steps, long time consumption and slow post-treatment in the traditional synthetic route, but also realizes convenient and rapid product separation

Method used

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  • Method for synthesizing 4,4'-bis(9h-carbazol-9-yl)biphenyls in one step
  • Method for synthesizing 4,4'-bis(9h-carbazol-9-yl)biphenyls in one step
  • Method for synthesizing 4,4'-bis(9h-carbazol-9-yl)biphenyls in one step

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Embodiment 1

[0023] A method for synthesizing 4,4'-bis(9H-carbazol-9-yl) biphenyl compounds in one step, comprising the steps of:

[0024]

[0025] In the carbazole compounds shown in formula II in this example, R 1 and R 2 Both are hydrogen, which is carbazole; R in the 1,4-diiodobenzene compounds shown in formula III 3 is hydrogen, is 1,4-diiodobenzene;

[0026] Under air atmosphere, 167 mg (1 mmol) of carbazole, 329 mg (1 mmol) of 1,4-diiodobenzene, 224 mg (2 mmol) of potassium tert-butoxide, CuCl 2 2H 2 O 171mg (1mmol), Ag 2 CO 3 Add 331mg (1.2mmol), 8mg (0.03mmol) of 18-crown-6 and 2.5mL of DMPU into the reactor, heat to 140°C and react for 48h. After the reaction is completed, cool down, spin out the solvent DMPU, add 50mL of dichloro Methane extraction, first washed with saturated sodium carbonate solution, and then washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the solvent DMPU was spin-off, followed by column chromatogr...

Embodiment 2

[0030] A method for synthesizing 4,4'-bis(9H-carbazol-9-yl) biphenyl compounds in one step, comprising the steps of:

[0031]

[0032] In the carbazole compounds shown in formula II in this example, R 1 and R 2 Both are methyl, respectively in the 3 and 6 positions of the carbazole skeleton, which is 3,6-dimethyl-9H-carbazole; in the 1,4-diiodobenzene compounds shown in formula III, R 3 is hydrogen, is 1,4-diiodobenzene;

[0033] Under air atmosphere, 3,6-dimethyl-9H-carbazole 195mg (1mmol), 1,4-diiodobenzene 329mg (1mmol), sodium tert-butoxide 224mg (2mmol), CuCl 2 2H 2 O 171mg (1mmol), Ag 2 CO 3 Add 331mg (1.2mmol), 18-crown ether-68mg (0.03mmol) and 2.5mL of DMPU into the reactor, heat to 130°C for 48h, after the reaction is finished, cool down, spin out the solvent DMPU, add 50mL of dichloromethane Extraction, first washed with saturated sodium carbonate solution, then washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, ...

Embodiment 3

[0037] A method for synthesizing 4,4'-bis(9H-carbazol-9-yl) biphenyl compounds in one step, comprising the steps of:

[0038]

[0039] In the carbazole compounds shown in formula II in this example, R 1 and R 2 Both are bromine, respectively at the 3-position and 6-position of the carbazole skeleton, which is 3,6-dibromo-carbazole; in the 1,4-diiodobenzene compounds shown in formula III, R 3 is hydrogen, is 1,4-diiodobenzene;

[0040] Under air atmosphere, 325 mg (1 mmol) of 3,6-dibromo-carbazole, 329 mg (1 mmol) of 1,4-diiodobenzene, 224 mg (2 mmol) of potassium tert-butoxide, CuCl 2 2H 2 O 171mg (1mmol), Ag 2 CO 3 Add 331 mg (1.2 mmol), 8 mg (0.03 mmol) of 18-crown-6 and 2.5 mL of DMPU into the reactor, heat to 120 ° C for 48 hours, after the reaction is completed, cool down, spin out the solvent DMPU, add 50 mL of di Chloromethane extraction, first washed with saturated sodium carbonate solution, then washed with saturated sodium chloride solution, dried over anhyd...

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Abstract

The invention relates to a method for one-step synthesis of 4,4'-bis(9H-carbazole-9-yl)biphenyl compounds, comprising the following steps: preparing carbazole compounds, 1,4-diiodobenzene compounds, organic bases , copper salt catalyst, silver salt oxidant, phase transfer catalyst and organic solvent are added to the reactor, and react at 120°C to 140°C for more than 12h under air atmosphere. After the reaction is completed, cool down, spin out the organic solvent, and extract , washing, drying, filtering, spin-off the organic solvent, and column chromatography separation to obtain 4,4'-bis(9H-carbazole-9-yl)biphenyl compounds. The method of the invention realizes the one-step method of synthesizing the product, and the product yield is high, and the preparation cost is low.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for one-step synthesis of 4,4'-bis(9H-carbazol-9-yl)biphenyl compounds. Background technique [0002] 4,4'-bis(9H-carbazol-9-yl)biphenyl (CBP) compounds are a class of arylamine dyes, which are important blue light materials. They have certain hole transport properties and are used in the research of OLEDs. has important applications. [0003] In the prior art, the synthetic method about 4,4'-bis(9H-carbazol-9-yl)biphenyl is as follows: [0004] It was reported in Synthesis, 1987, 383 that under the catalysis of metal copper salt, the corresponding triarylamine was synthesized by coupling reaction of diarylamine and iodobenzene. It was reported in Chem.Mater.1998,10,2235-2250 that under the catalysis of metal copper salt (the conditions of the aforementioned literature), the corresponding 4,4'- Bis(9H-carbazol-9-yl)biphenyl. It was reported in Organic Elect...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/86C07D209/88
CPCC07D209/86C07D209/88
Inventor 丁鹏飞张金涛陈建欣许鹏孙潇楠刘天宇王玮苏扬张美琪夏雨诗
Owner CHANGZHOU INST OF TECH
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