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5,5'-diaryl-3,3'-diamino-4,4'-dimethoxybenzophenone compound and preparation method thereof

A technology of dimethoxybenzophenone and diamino, which is applied in the field of organic synthesis, can solve the problems of limited application, poor solubility of polyimide, and difficult film formation, etc., and achieves convenient operation, reduced production cost, good thermal The effect of stability

Inactive Publication Date: 2017-05-31
JIANGSU MO OPTO ELECTRONICS MATERIAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the poor solubility of the obtained polyimide, it is not easy to form a film, which greatly limits its application in storage.

Method used

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  • 5,5'-diaryl-3,3'-diamino-4,4'-dimethoxybenzophenone compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] A kind of preparation method of 5,5'-diaryl-3,3'-diamino-4,4'-dimethoxybenzophenone compound, its preparation method is as follows:

[0030] (I) Synthesis of 3,3'-dinitro-4,4'-dimethoxybenzophenone:

[0031] In a 250mL three-neck flask, add 12g Cu(NO 3 ) 2 ·3H 2 O (50.00mmol), 35mLHAc and 70mL Ac 2 O, stirred at room temperature for 10 min to make Cu(NO 3 ) 2 ·3H 2 O was dissolved, and 4,4'-dimethoxybenzophenone was slowly added to the three-necked flask in batches within 15 minutes, and the temperature was raised to 80°C for 2 hours, followed by TLC spotting, until 4,4'-dimethyl Until the reaction of oxybenzophenone is completed, the reaction solution is poured into distilled water, so that a large amount of white solids are precipitated, filtered under reduced pressure and the filter cake is washed with saturated NaHCO 3 , washed with distilled water, and dried at 80°C to obtain 10.22g of the product 3,3'-dinitro-4,4'-dimethoxybenzophenone, with a yield of 75%....

Embodiment 2

[0039] A kind of preparation method of 5,5'-diaryl-3,3'-diamino-4,4'-dimethoxybenzophenone compound, its preparation method is as follows:

[0040] Steps (I), (II), (III) are the same as in Example 1;

[0041] (IV) Synthesis of 5,5'-bis(4''-α-naphthyl)phenyl-3,3'-diamino-4,4'-dimethoxybenzophenone:

[0042] in N 2 Under protection, add 0.43 g of 5,5'-dibromo-3,3'-diamino-4,4'-dimethoxybenzophenone (1.00 mmol), 0.54g4-(α-naphthyl)phenylboronic acid (2.20mmol), 0.0347gPd(PPh 3 ) 4 (0.02mmol), 0.424g Na 2 CO 3(4.00mmol), 10mL toluene and 5mL distilled water, heated to 110°C for reflux reaction for 6h, a large number of bubbles were generated during the reaction, and tracked by TLC spot plate, after the reaction was complete, cooled to room temperature, filtered to remove insoluble matter, and the filtrate was used A separatory funnel was used to separate the liquid, and the separated aqueous layer was extracted three times with toluene, the extracted organic layers were com...

Embodiment 3

[0044] A kind of preparation method of 5,5'-diaryl-3,3'-diamino-4,4'-dimethoxybenzophenone compound, its preparation method is as follows:

[0045] Steps (I), (II), (III) are the same as in Example 1;

[0046] (IV) Synthesis of 5,5'-bis(4''-9H-carbazolyl)phenyl-3,3'-diamino-4,4'-dimethoxybenzophenone:

[0047] in N 2 Under protection, add 0.30 g of 5,5'-dibromo-3,3'-diamino-4,4'-dimethoxybenzophenone (0.70 mmol), 0.44g4-(9H-carbazolyl)phenylboronic acid (1.54mmol), 0.0243g Pd(PPh 3 ) 4 (0.014mmol), 0.30g Na 2 CO 3 (2.80mmol), 10mL toluene and 5mL distilled water, heated to 100°C for reflux reaction for 6h, a large number of bubbles were generated during the reaction, and tracked by TLC spot plate, after the reaction was complete, cooled to room temperature, filtered to remove insoluble matter, and the filtrate was used A separatory funnel was used to separate the liquid, and the separated aqueous layer was extracted twice with toluene, the extracted organic layers were c...

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Abstract

The invention relates to a 5,5'-diaryl-3,3'-diamino-4,4'-dimethoxybenzophenone compound and a preparation method thereof. The preparation method comprises the following steps: carrying out nitrification on 4,4'-dimethoxybenzophenone firstly to obtain 3,3'-binitro-4,4'-dimethoxybenzophenone, then carrying out reaction on the 3,3'-binitro-4,4'-dimethoxybenzophenone and N-bromosuccinimide (NBS) under the acid condition to produce 5,5'-dibromo-3,3'-binitro-4,4'-dimethoxybenzophenone, then adding a reducing agent to covert the 5,5'-dibromo-3,3'-binitro-4,4'-dimethoxybenzophenone to 5,5'-dibromo-3,3'-diamino-4, 4'-dimethoxybenzophenone, and finally carrying out reaction on the 5,5'-dibromo-3,3'-diamino-4,4'-dimethoxybenzophenone and arylboronic acid containing various large conjugated groups to obtain the 5,5'-diaryl-3,3'-diamino-4,4'-dimethoxybenzophenone compound containing large conjugated groups. The 5,5'-diaryl-3,3'-diamino-4,4'-dimethoxybenzophenone compound and the preparation method thereof are simple in synthesis route, convenient to operate, high in yield and cheap and available in raw materials, and thus the production cost is greatly lowered.

Description

technical field [0001] The invention relates to a 5,5'-diaryl-3,3'-diamino-4,4'-dimethoxybenzophenone compound and a preparation method thereof, belonging to the technical field of organic synthesis. Background technique [0002] Polyimide material (PI) is a kind of polymer material with excellent comprehensive performance and wide application fields. After more than 100 years of development, it has high thermal stability, good mechanical properties, low dielectric constant, wide solubility A series of excellent properties such as good corrosion performance have been applied in many fields such as aviation, aerospace, medicine, chemical industry, etc. However, due to the rigid structure of its main chain, most polyimides have poor solubility, meltability and processing properties , the application field is greatly limited. [0003] There are strong interactions within and between polyimide molecular chains, so that its molecular chains can be tightly packed, thereby improvi...

Claims

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Application Information

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IPC IPC(8): C07C225/22C07C221/00C07D209/86
CPCC07C225/22C07D209/86
Inventor 沈应中朱雅亮赵静陶弦汤清云沈克成祁欣
Owner JIANGSU MO OPTO ELECTRONICS MATERIAL
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