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A kind of diamine compound containing m-terphenyl structure and its synthesis method and application

A technology for m-terphenyl and amine compounds, which is applied to diamine compounds containing m-terphenyl structure and the fields of synthesis and application thereof, can solve the problems of difficult processing and molding, application limitation, insoluble and insoluble polyimide, etc. Interaction force, improved solubility, easy purification effect

Active Publication Date: 2017-01-04
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most polyimides are infusible and insoluble, making them difficult to process and shape, thus limiting their application

Method used

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  • A kind of diamine compound containing m-terphenyl structure and its synthesis method and application
  • A kind of diamine compound containing m-terphenyl structure and its synthesis method and application
  • A kind of diamine compound containing m-terphenyl structure and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1: Synthesis of 5'-(4-(trifluoromethyl)phenyl)-[1,1':3',1"-terphenyl]-3,3"-diamine

[0037] (1) In a three-necked flask, add 11.25g (50mmol) of 4-bromobenzotrifluoride, 9.54g (55mmol) of p-aminophenyl borate hydrochloride, 75ml of 2mol / L potassium carbonate solution and 250ml of tetrahydrofuran, magnetically stir and pass Argon, after heating the oil bath to 75°C, add 0.02g tetrakistriphenylphosphine palladium, reflux for 12h and then let it stand, separate the liquid to remove the water layer, then mix with silica gel and spin dry to pass through the chromatographic column, collect the product point solution and spin dry to get white The solid was dried in vacuum at 60° C. for 12 h to obtain 11.3 g of a white intermediate product 4-Amino-4'-(trifluoromethyl)-1,1'-biphenyl with a yield of 95%. The intermediate structure is as follows:

[0038]

[0039] (2) In a three-necked flask, add 4-Amino-4'-(trifluoromethyl)-1,1'-biphenyl 7.12g (30mmol) and 30ml of DMF ...

Embodiment 2

[0049] Example 2: Synthesis of 5'-(4-fluorophenyl)-[1,1':3',1″-terphenyl]-3,3″-diamine

[0050] (1) In a three-necked flask, add 8.75g (50mmol) of 4-bromofluorobenzene, 9.54g (55mmol) of p-aminophenyl borate hydrochloride, 75ml of 2mol / L potassium carbonate solution, a few drops of phase transfer catalyst and 250ml of tetrahydrofuran , magnetic stirring and argon gas, after heating the oil bath to 75°C, add 0.02g tetrakistriphenylphosphine palladium, reflux for 12h, let stand for liquid separation to remove the water layer, then mix with silica gel and spin dry, pass through the chromatography column, and collect the product point The solution was spin-dried to obtain a white solid, which was dried in vacuum at 60°C for 12 hours to obtain 8.61 g of a white intermediate product 4'-fluoro-[1,1'-biphenyl]-4-amine with a yield of 92%. The intermediate structure is as follows:

[0051]

[0052] (2) In a three-necked flask, add 5.62g (30mmol) of 4'-fluoro-[1,1'-biphenyl]-4-amine...

Embodiment 3

[0062] Example 3: Synthesis of 5'-(3,5-bis(trifluoromethyl)phenyl)-[1,1':3',1″-terphenyl]-3,3″-diamine

[0063] (1) In a three-necked flask, add 1-bromo-3,5-bis(trifluoromethyl)benzene14.65g (50mmol), p-aminophenyl borate hydrochloride 9.54g (55mmol), 2mol / L potassium carbonate solution 75ml and 250ml tetrahydrofuran, magnetically stirred and argon, heated to 75°C in an oil bath, added 0.02g tetrakistriphenylphosphine palladium, refluxed for 12 hours, left to separate liquids to remove the water layer, mixed with silica gel, spin-dried, and passed through the chromatography column. The collected product point solution was spin-dried to obtain a white solid, which was dried in vacuum at 60°C for 12 hours to obtain 14.50 g of the white intermediate product 3',5'-bis(trifluoro-methyl)-[1,1'-biphenyl]-4-amine. The rate is 94%. The intermediate structure is as follows:

[0064]

[0065] (2) In a three-necked flask, add 3',5'-bis(trifluoromethyl)-[1,1'-biphenyl]-4-amine9.16g (3...

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Abstract

The invention discloses a diamine compound containing an m-terphenyl structure, a synthesis method and application thereof. The invention utilizes halogenated aromatic hydrocarbons to introduce an amino group through Suzuki reaction, and then obtains a functional diamine compound containing m-terphenyl structure through bromination, diazotization, Suzuki coupling and reduction. The synthesis method of the diamine compound has simple process and high yield, and the synthesized compound has certain fluorescence characteristics. The diamine compound of the present invention can be used for synthesizing high-performance, functionalized polymers such as polyamide, polyimide, polyamide-imide and polyester-imide, and is especially suitable for preparing soluble, colorless and transparent High-performance functional polyimide material with fluorescent properties.

Description

technical field [0001] The present invention relates to the field of material science and technology, in particular to a diamine compound containing m-terphenyl structure and a synthesis method thereof. The diamine compound has certain fluorescence characteristics and can be used for synthesizing polyamide, polyimide, polyamide imide High-performance, functionalized polymers such as amines and polyesterimides are especially suitable for the preparation of high-performance functionalized polyimide materials that are soluble, colorless and transparent, and have certain fluorescent properties. [0002] technical background [0003] Polyimide is currently industrialized due to its excellent heat resistance, thermal stability, mechanical strength, dielectric properties, chemical resistance, radiation resistance, and outstanding toughness and flexibility. One of the varieties with the best heat resistance in engineering plastics. Since it was developed and industrialized by DuPont...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/52C07C209/36C08G69/00C08G73/10
Inventor 张艺胡启彬许家瑞刘四委池振国
Owner SUN YAT SEN UNIV