9-([1, 1 '-biphenyl]-3-yl)-9-phenyl-2-bromofluorene and synthesis method thereof

A synthesis method, biphenyl technology, applied in chemical instruments and methods, preparation of hydroxyl compounds, magnesium organic compounds, etc., can solve the problems of no literature reports on the synthesis method, and achieve excellent thermal stability, high melting temperature, and production cost low effect

Inactive Publication Date: 2021-07-23
HENAN ACADEMY OF SCI CHEM RES INST CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, 9-([1,1'-biphenyl]-3-yl)-9-phenyl-2-bromofluorene and its synthesis method have not been reported in the literature

Method used

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  • 9-([1, 1 '-biphenyl]-3-yl)-9-phenyl-2-bromofluorene and synthesis method thereof
  • 9-([1, 1 '-biphenyl]-3-yl)-9-phenyl-2-bromofluorene and synthesis method thereof
  • 9-([1, 1 '-biphenyl]-3-yl)-9-phenyl-2-bromofluorene and synthesis method thereof

Examples

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Effect test

example 1

[0021] Under the protection of argon, add 130.2 g of magnesium powder to a 2 L three-necked flask, add 600 mL of methyl tetrahydrofuran solution to immerse the magnesium powder, then add dropwise 100 g (0.43 mol) of 3-bromobiphenyl in methyl tetrahydrofuran solution, and react The temperature was controlled at 50°C. After 2 hours, the reaction of 3-bromobiphenyl was detected by gas chromatography, and 111.4 g of 2-bromofluorenone solid was added in batches and stirred overnight. After the reaction was completed, 500 mL of water was added to terminate the reaction, the organic layer was separated, dried over anhydrous sodium sulfate, filtered with suction, and the solvent was recovered by distillation under reduced pressure, and dispersed by adding 500 mL of n-hexane to obtain a white solid 9-([1,1' -biphenyl]-3-yl)-9-hydroxy-2-bromofluorene (compound 1). In a 2 L three-necked flask, compound 1 was dissolved in 500 mL of benzene, the reaction temperature was controlled to -10 °...

example 2

[0027] Under the protection of argon, add 117.5 g of magnesium powder to a 2 L three-necked flask, add 700 mL of methyl tetrahydrofuran solution to immerse the magnesium powder, then add dropwise 130.5 g (0.56 mol) of 3-bromobiphenyl in methyl tetrahydrofuran solution, and react The temperature was controlled at 60 °C. After 2 h, the reaction of 3-bromobiphenyl was detected by gas chromatography, and 159.6 g of 2-bromofluorenone solid was added in batches and stirred overnight. After the reaction was completed, 700 mL of water was added to terminate the reaction, the organic layer was separated, dried over anhydrous sodium sulfate, filtered with suction, the solvent was recovered by distillation under reduced pressure, and 600 mL of n-hexane was added to disperse to obtain a white solid 9-([1,1' -biphenyl]-3-yl)-9-hydroxy-2-bromofluorene (compound 1). In a 2 L three-necked flask, compound 1 was dissolved in 400 mL of benzene, the reaction temperature was controlled to -15 °C, ...

example 3

[0029] Under argon protection, 120.1 g of magnesium powder was added to a 2 L three-necked flask, 500 mL of methyl tetrahydrofuran solution was added to immerse the magnesium powder, and then 74.6 g (0.32 mol) of 3-bromobiphenyl in methyl tetrahydrofuran solution was added dropwise, and the reaction The temperature was controlled at 70 °C. After 2 h, the reaction of 3-bromobiphenyl was detected by gas chromatography, and 74.6 g of 2-bromofluorenone solid was added in batches and stirred overnight. After the reaction was completed, 700 mL of water was added to terminate the reaction, the organic layer was separated, dried over anhydrous sodium sulfate, filtered with suction, the solvent was recovered by distillation under reduced pressure, and 700 mL of n-hexane was added to disperse to obtain a white solid 9-([1,1' -biphenyl]-3-yl)-9-hydroxy-2-bromofluorene (compound 1). In a 2 L three-necked flask, compound 1 was dissolved in 600 mL of benzene, the reaction temperature was co...

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Abstract

The invention discloses 9-([1, 1 '-biphenyl]-3-yl)-9-phenyl-2-bromofluorene and a synthesis method thereof, and belongs to the field of organic chemical synthesis. The structure of 9-([1, 1 '-biphenyl]-3-yl)-9-phenyl-2-bromofluorene is disclosed in the invention, and is realized by the following method: taking 3-brominated biphenyl as an initial raw material, and synthesizing 9-([1, 1'-biphenyl]-3-yl)-9-phenyl-2-bromofluorene through Grignard reaction, nucleophilic substitution reaction and intermolecular dehydration reaction. The synthesis method disclosed by the invention is simple to operate, low in production cost and suitable for industrial production, and the application of the fluorene derivatives as intermediates in design and synthesis of organic photoelectric materials is expanded.

Description

technical field [0001] The invention relates to a fluorene derivative and a synthesis method thereof, in particular to a 9-([1,1'-biphenyl]-3-yl)-9-phenyl-2-bromofluorene and a synthesis method thereof. It belongs to the field of organic chemical synthesis. Background technique [0002] Organic electroluminescent devices have the characteristics of ultra-thin, simple structure, low energy consumption, fast response, full curing and active luminescence, and have a wide range of material choices and low cost. Therefore, as a new generation of flat-panel display technology, organic electroluminescent devices show broad application prospects in the fields of flat-panel displays and solid-state lighting, which has attracted the attention of many researchers. Fluorene has high photothermal stability, the fluorescence quantum efficiency of solid fluorene can reach 60%-80%, and the band gap energy is greater than 2.90 eV, but the rigid planar biphenyl unit of fluorene makes the mat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C25/22C07C17/263C09K11/06
CPCC07C25/22C07C17/263C07C29/40C07F3/02C09K11/06C07C2603/18C09K2211/1011C07C35/52
Inventor 刘畅杨振强王朝杰李奎杨森化林
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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