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Aromatic diamine compound containing imide structure as well as preparation method and application thereof

An aromatic diamine and imide-containing technology, applied in the field of aromatic diamine compounds and their preparation, can solve the problems of incomplete mechanism and insufficient application, and achieve unique fluorescence characteristics, simple process, good thermal stability and solubility. Effect

Active Publication Date: 2013-06-12
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is not perfect to systematically develop the relationship between structure and performance and its mechanism, and it is far from enough to broaden its application. Therefore, it is necessary to carry out further in-depth research on the systematic design and synthesis of diamine monomers.

Method used

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  • Aromatic diamine compound containing imide structure as well as preparation method and application thereof
  • Aromatic diamine compound containing imide structure as well as preparation method and application thereof
  • Aromatic diamine compound containing imide structure as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1: Synthesis of 4-(Bis(4-aminophenyl)amino)-N,N-diphenylbenzamide, whose structural formula is as follows:

[0035] (1) Synthesis of intermediate 4-Nitro-N,N-diphenylbenzamide

[0036] Weigh 3.3846g (20mmol) of diphenylamine into a 100ml three-necked flask, add 40ml of tetrahydrofuran and 2.0123ml (25mmol) of pyridine and pass through argon, stir for 30min under ice-salt bath conditions, and weigh an equimolar amount of p-nitro Benzoyl chloride was added to the three-necked flask in batches, and the reaction was stirred until the temperature reached room temperature, and the temperature was raised to 60°C for more than 6 hours. After the reaction was completed, the solvent tetrahydrofuran was spin-dried with a rotary evaporator, dissolved in dichloromethane, purified by column chromatography, and dried under vacuum at 60°C overnight to obtain 3.8 g of a light green product with a yield of 61%. The chemical formula of this intermediate is C19H14O3N2, molecular...

Embodiment 2

[0046] Example 2: Synthesis of 4-(Bis(4-aminophenyl)amino)-N,N-bis(4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)-benzamide, whose structural formula is as follows Shown:

[0047]

[0048] (1) Synthesis of intermediate 4,4'-Bisbromophenyl Amine

[0049] Weigh 5g (29.6mmol) of diphenylamine into a 250ml three-neck flask, use 50ml of dimethylformamide (DMF) as a solvent, stir magnetically and pass in argon, stir for 30min under ice-salt bath conditions, weigh 59.2mmol (10.53 g) N-bromosuccinimide (NBS) was dissolved in 50ml of DMF, added dropwise into a three-necked flask and completed dropwise within 30min, and reacted for 6h under ice-salt bath conditions. After the reaction was completed, the reaction solution was poured into ice-salt water and vigorously stirred to precipitate a gray solid, which was filtered with suction and washed three times with saturated sodium bicarbonate (NaHCO3) solution, and dried in vacuum at 60°C overnight to obtain 8.8 g of the product, with a yi...

Embodiment 3

[0065] Example 3: Synthesis of N,N-bis(4'-amino-[1,1'-biphenyl]-4-yl)-4-nitrobenzamide, whose structural formula is as follows:

[0066]

[0067] (1) Synthesis of intermediate 4,4'-Bisbromophenyl Amine

[0068]

[0069] (2) Synthesis of intermediate N,N-bis(4-bromophenyl)-4-nitrobenzamide

[0070]

[0071] The above two intermediates were synthesized according to the method of Example 2.

[0072](3) Synthesis of diamine monomer N,N-bis(4'-amino-[1,1'-biphenyl]-4-yl)-4-nitrobenzamide

[0073] Add 11.9g (25mmol) of 4,4'-Bisbromophenyl Amine and 7.53g (55mmol) of p-aminophenyl borate hydrochloride into a 250ml three-neck flask, add 100ml of tetrahydrofuran as a solvent, and then add 82.5ml of 2M potassium carbonate solution , magnetically stirred and fed with argon, after the oil bath temperature was heated to 70°C, a catalyst amount of tetrakistriphenylphosphine palladium was added, and after reflux reaction for 24 hours, the reaction solution was spin-dried and purif...

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Abstract

The invention discloses an aromatic diamine compound containing an imide structure as well as a preparation method and application thereof. The method for preparing the aromatic diamine compound containing the imide structure comprises the following steps of: preparing a rigid non-planar distorted structural intermediate containing the imide structure by high reaction activity of acyl chloride and active hydrogen; introducing different chemical groups through the Suzuki reaction of halogen elements and boric acid ester; utilizing fluoronitrobenzene to react with amino so as to preparing a binitro product by reaction of fluoronitrobenzene and amino; and reducing to obtain a novel aromatic diamine compound containing the imide structure. The synthesizing method is simple, easy to purify and high in yield; the synthesized compound has unique fluorescent characteristic, excellent thermal property and solubility property, can be used as a photoelectric material and a monomer for synthesizing novel high-performance polymers such as polyamide, polyimide, polyamide imide and polyester imide.

Description

technical field [0001] The invention relates to the field of polymer material science, in particular to an aromatic diamine compound containing an imide structure and its preparation method and application. The diamine compound can be used not only as a photoelectric material, but also as a monomer for synthesis New high-performance polymers such as polyamides, polyimides, polyamideimides and polyesterimides. Background technique [0002] As a class of high-performance polymers, polyimide has excellent heat resistance, thermal stability, high mechanical strength, excellent dielectric properties, good chemical resistance, radiation resistance, and has Outstanding toughness and softness, etc., can be used as film materials, coatings, adhesive materials, foams, fibers and advanced composite material substrates in aerospace, aviation, microelectronics and military fields. Since DuPont produced polypyromellitic film and plastics in the 1960s, and successively applied them in adh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/40C07C233/80C07C231/12C09K11/06C08G69/00C08G73/10C08G73/14C08G73/16
Inventor 张艺孙华伟许家瑞刘四委池振国
Owner SUN YAT SEN UNIV
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