Diarylfluorene intermediate preparation method

A technology of diarylfluorene and intermediate, which is applied in the field of preparation of diarylfluorene intermediate material, can solve the problems of complicated separation and purification of intermediate tertiary alcohol, cumbersome preparation of grignard reagent, etc., and achieves the effects of environmental friendliness and simple operation.

Inactive Publication Date: 2010-02-10
NANJING UNIV OF POSTS & TELECOMM
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  • Abstract
  • Description
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AI Technical Summary

Problems solved by technology

This method overcomes the shortcomings of the traditional Grignard reagent-Fourierian two-step synthesis method, such as the cumbersome preparation of the Grignard reagent and the complicated separation and purification of the intermediate tertiary alcohol. The obtained intermediate products and diarylfluorene intermediates are all organic functional An important organic intermediate with a wide range of uses in the material, the whole reaction system is simple, the process is simple, the raw material is cheap and easy to obtain, the yield is high, and the environment is friendly

Method used

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  • Diarylfluorene intermediate preparation method
  • Diarylfluorene intermediate preparation method
  • Diarylfluorene intermediate preparation method

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Embodiment 1:9,9,-the synthesis of two (phenyl) fluorenes

[0033] In a 100mL single-necked flask, add fluorenone (0.9g, 0.005mol, 1eq.), aniline hydrochloride (2.0g, 0.015mol, 3eq.), aniline (10mL), and heat at 150°C for 4 hours under nitrogen protection. After cooling slightly, pour it into 10wt% NaOH solution (50mL), stir for 4h, filter to get pale scarlet fluffy needles, wash with ethanol to remove the pigment, recrystallize with ethanol, and dry in vacuo to obtain a white solid with a melting point of 236-238°C; The air-dried white solid, that is, 9,9'-bis(4-aminophenyl)fluorene (0.348g, 0.001mmol, 1eq.) and 20mL of dichloromethane were added to a 100mL single-necked flask, protected by nitrogen, heated to 40 ° C, 15 Add 0.4mL alkyl nitrite dropwise within 2 minutes, keep reflux for 2h, cool to room temperature, filter off insoluble matter, transfer to a separatory funnel, add 20mL 1M hydrochloric acid, 20mL 10% sodium hydroxide to wash, separate liquid, collect or...

Embodiment 2

[0034] Example 2: Synthesis of 2-bromo-9,9'-bis(phenyl)fluorene

[0035]In a 100mL single-necked flask, add 2-bromofluorenone (1.30g, 0.005mol, 1eq.), aniline hydrochloride (2.0g, 0.015mol, 3eq.), aniline (10mL), and heat at 150°C under nitrogen protection After 4 hours, cool down slightly and pour into 10wt% NaOH solution (50mL), stir for 4h, filter to get light scarlet fluffy needles, wash with ethanol to remove pigment, recrystallize with ethanol, and dry in vacuo to obtain a white solid, melting point 236-238 ℃; The air-dried white solid is 2-bromo-9,9'-bis(4-aminophenyl)fluorene (0.427g, 0.001mmol, 1eq.) and 20mL of dichloromethane were added to a 100mL single-necked flask, nitrogen protection , heated to 40°C, added dropwise 0.4mL alkyl nitrite within 15 minutes, kept reflux for 2h, cooled to room temperature, filtered off insoluble matter, transferred to a separatory funnel, added 20mL 1M hydrochloric acid, 20mL 10% sodium hydroxide in sequence Wash, separate, collect ...

Embodiment 3

[0037] Embodiment 3: 2,7-dibromo-9,9,-the synthesis of two (phenyl) fluorenes

[0038] In a 100mL single-necked flask, add 2,7-dibromofluorenone (1.68g, 0.005mol, 1eq.), aniline hydrochloride (2.0g, 0.015mol, 3eq.), aniline (10mL), under nitrogen protection Heated at 150°C for 4 hours, cooled slightly, poured into 10wt% NaOH solution (50mL), stirred for 4 hours, filtered to obtain light scarlet fluffy needles, washed with ethanol to remove pigment, recrystallized with ethanol, and dried in vacuo to obtain a white solid, melting point 236-238°C; Air-dried white solid, namely 2,7-dibromo-9,9'-bis(4-aminophenyl)fluorene (0.506g, 0.001mmol, 1eq.) and 20mL of dichloromethane were added to 100mL In a single-necked flask under nitrogen protection, heat to 40°C, add 0.4 mL of alkyl nitrite dropwise within 15 minutes, keep reflux for 2 hours, cool to room temperature, filter out insoluble matter, transfer to a separatory funnel, add 20 mL of 1M hydrochloric acid in sequence, Wash with...

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Abstract

The invention provides a diarylfluorene intermediate preparation method and relates to the application field of fine organic synthesis and photovaltaic material. Diarylfluorene can be used as an important intermediate in the material fields such as organic electroluminescence, photovoltaic cells, organic electrical storage, organic non-linear optics, chemical sensor and biosensor, organic laser and the like. The preparation method of diarylfluorene intermediate comprises the following two specific steps: (1) using arylamine, arylamine hydrochloride and fluorenone or the derivative of fluorenone to react under heat condition, alkalifying, stirring, filtrating and washing to obtain high purity intermediate product; (2) adding the intermediate product in dichloromethane to react with alkyl nitrite on the condition of refluxing and finally obtaining the high purity target product through recrystallization. The diarylfluorene intermediate preparation method has the advantage that (1) two-step method is adopted to prepare diarylfluorene intermediate, the raw material is cheap, the steps are simple, the yield is high and the product is easy to purify; (2) the method has mass production value and is environmentally friendly.

Description

technical field [0001] The invention specifically relates to a preparation method of a diaryl fluorene intermediate material, and relates to steps and raw materials used in the preparation process of these materials. technical background [0002] Since 1987, the Tang research group [Tang, C.W.; Van Slyke, S.A.Appl.Phys.Lett.1987, 51, 913.] of Kodak Corporation of the United States published a thin-film organic electroluminescent device (Organic Light- emitting Diodes) and since then, organic flat panel display has become another generation of market-oriented display products after liquid crystal display. At the same time, other organic electronics and optoelectronic industries, including fields such as organic field effect transistors, organic solar cells, nonlinear optics, biosensing and lasers, and nonlinear optical materials are also moving towards marketization. The advantages of organic and plastic electronics lie in the low cost of material preparation, simple process...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C13/567C07C1/32C07C25/22C07C17/26
Inventor 解令海黄维赵剑锋常永正林宗琼钱妍
Owner NANJING UNIV OF POSTS & TELECOMM
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