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Synthesis method of 9,9'-spirobifluorene derivative

A technology of spirobifluorene and its derivatives, which is applied in the field of organic chemical synthesis, can solve the problems of 2-bromobiphenyl being expensive, affecting potential applications, and difficult to industrialize production, so as to meet the needs of industrialized production and achieve low cost and cost reduction. Effect

Active Publication Date: 2013-10-02
PUYANG HUICHENG ELECTRONICS MATERIAL +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the price of 2-bromobiphenyl in the market is expensive and the supply is insufficient, resulting in the high price of bromo-9,9'-spirobifluorene, which eventually makes 9,9'-spirobifluorene diphenylphosphine derivatives It is difficult to produce industrially, which affects its potential application in luminescent materials

Method used

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  • Synthesis method of 9,9'-spirobifluorene derivative
  • Synthesis method of 9,9'-spirobifluorene derivative
  • Synthesis method of 9,9'-spirobifluorene derivative

Examples

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example 1

[0017]

[0018] Under the protection of argon, the reaction temperature was controlled at 100 °C, and 10 mL of o-bromochlorobenzene (0.1 mmol) in methyl tetrahydrofuran was dropped into 5 mL of phenylmagnesium bromide (0.15 mmol) in methyl tetrahydrofuran, and the reaction was stirred for 20 h. Then drop the above reaction solution into 10 mL of 2-bromofluorenone (0.1 mmol) ether solution, reflux for 2 h, hydrolyze, filter, and react the solid in 5 mL of mixed acid (glacial acetic acid and hydrochloric acid) at 75 °C for 4 h, After filtration, the crude solid was separated by column chromatography (200-300 mesh silica gel) using a dichloromethane-n-hexane mixed solvent as the eluent to obtain 30.0 mg of 2-bromo-9,9'-spirobifluorene, with a yield of 76.0%. The obtained 2-bromo-9,9'-spirobifluorene was reacted with lithium diphenylphosphine (0.075 mmol) in 10 mL of tetrahydrofuran solvent. After reflux for 5 h, 10 mL of methanol was added to the reaction solution, and the sol...

example 2

[0024]

[0025] Under argon protection, control the reaction temperature at 80 °C, drop 10 mL of o-dibromobenzene (0.1 mmol) in methyl tetrahydrofuran solution into 5 mL of phenylmagnesium bromide (0.11 mmol) in methyl tetrahydrofuran solution, and stir the reaction 12 h. Then drop the above reaction solution into 10 mL of 2,7-dibromofluorenone (0.1 mmol) ether solution, heat to reflux for 2 h, hydrolyze, filter, and dissolve the solid in 5 mL of mixed acid (glacial acetic acid and hydrochloric acid) at 75 °C React for 4 h, filter to obtain a solid, and use dichloromethane-n-hexane mixed solvent as eluent for column chromatography (200-300 mesh silica gel) to obtain the product 2,7-dibromo-9,9'-spirobifluorene 36.2 mg , yield 76.2%. The 2,7-dibromo-9,9'-spirobifluorene obtained above was reacted with lithium diphenylphosphine (0.15 mmol) in tetrahydrofuran solvent, and after reflux for 12 h, methanol was added to the reaction solution, and the solid was obtained by filtrat...

example 3

[0031]

[0032] Under argon protection, control the reaction temperature at 50 °C, drop 10 mL of o-bromoiodobenzene (0.1 mmol) in methyl tetrahydrofuran solution into 5 mL of phenylmagnesium bromide (0.09 mmol) in methyl tetrahydrofuran solution, and stir the reaction 8 h. Then drop the above reaction solution into 5 mL of 2-bromofluorenone (0.1 mol) ether solution, reflux for 2 h, hydrolyze, and filter to obtain a solid. React in 10 mL of mixed acid (glacial acetic acid and hydrochloric acid) at 75°C for 4 h, and filter , the obtained solid was separated by column chromatography (200-300 mesh silica gel) using a dichloromethane-n-hexane mixed solvent as the eluent, and dried to obtain 30.9 mg of 2-bromo-9,9'-spirobifluorene, with a yield of 78.2%. The 2-bromo-9,9'-spirobifluorene obtained above was reacted with lithium diphenylphosphine (0.075 mmol) in 5 mL of tetrahydrofuran, and after reflux for 5 h, methanol was added to obtain a solid, which was washed with water and f...

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Abstract

The invention discloses a synthesis method of a 9,9'-spirobifluorene derivative, and belongs to the field of organic chemical synthesis. The method comprises the steps that 2-bromochlorobenzene as a raw material acts with phenylmagnesium bromide and then reacts with bromofluorenone at 50-100 DEG C in a methyltetrahydrofuran solvent, hydrolysis and filtration are performed, solid performs closed-loop synthesis under acid catalysis to produce bromo-9,9'-spirobifluorene, and bromo-9,9'-spirobifluorene reacts with lithium diphenylphosphide to synthesize the 9,9'-spirobifluorene diphenylphosphine derivative. The synthesis method is simple in process; raw materials are low in price and easy to obtain; the production cost of series products is obviously lowered during synthesis; and the application of the fluorene derivative in design and synthesis of organic photoelectric materials as an intermediate is extended.

Description

technical field [0001] The invention relates to a synthesis method of a class of organic phosphine derivatives, in particular to a synthesis method of a class of 9,9'-spirobifluorene derivatives, belonging to the field of organic chemical synthesis. Background technique [0002] Organic electroluminescent materials have the advantages of wide material selection, low energy consumption, high efficiency and luminous brightness, ultra-thin, full curing, fast response, active light emission, and large-area flexible display, etc., and are expected to become the new generation of flat panel display technology. The core component has become one of the research hotspots in the fields of organic electronics and optoelectronic information. Fluorene-based organophosphine derivatives are a class of luminescent materials with broad application prospects. Fluorene has high photothermal stability, solid-state fluorene fluorescence quantum efficiency as high as 60%-80%, and band gap energ...

Claims

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Application Information

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IPC IPC(8): C07F9/50
Inventor 杨振强杨瑞娜蒋卫鹏周铎冯培培屈凤波
Owner PUYANG HUICHENG ELECTRONICS MATERIAL
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