Novel diamine compound, and preparation method and application thereof

An amine compound, a new type of technology, applied in the field of material science, can solve problems such as failure to achieve, and achieve the effects of easy purification, high yield, and simple synthesis process

Active Publication Date: 2015-02-11
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In recent years, most scholars have focused on the research of nanoporous polymer materials and organic-inorganic hybrid materials, using the introduction of micro-nanopores to make the dielectric constant of the material meet the current high-performance VLSI dielectric con...

Method used

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  • Novel diamine compound, and preparation method and application thereof
  • Novel diamine compound, and preparation method and application thereof
  • Novel diamine compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] N1-(4-aminophenyl)-N1-(4'-(2,2-diphenylvinyl)biphenyl-4-yl)benzene-1,4-diamine (Tri-TPA-2NH 2 )Synthesis

[0027]

[0028] (1) Synthesis of intermediate 1-(2-(4-bromophenyl)-1-phenylvinyl)benzene.(Tri-Br):

[0029] Add 40.00 g of p-bromobenzyl bromide (0.16 mol) and 83.6 mL of triethyl phosphite (0.48 mol) into a 500 ml three-necked flask, stir magnetically and pass argon, heat and reflux in an oil bath at 150°C for 24 hours, then cool to room temperature, Obtain the ylide reagent. Add 450ml of tetrahydrofuran (THF) to the three-necked flask, then add 21.87g of benzophenone (0.12mol) and 40.39g of potassium tert-butoxide (t-BuOK, 0.36mol), stir magnetically for 24h, after the reaction stops, react The solution was poured into water for extraction, and a large amount of white precipitates precipitated out. The precipitates were collected by filtration with a funnel, washed with ethanol three times, and dried in vacuum at 60°C for 24 hours to obtain a white intermedi...

Embodiment 2

[0042] (E)-N1-(4-aminophenyl)-N1-(4'-(1,2-diphenylvinyl)biphenyl-4-yl)benzene-1,4-diamine(San-TPA-2NH 2 )

[0043]

[0044] (1) Synthetic intermediate (E)-1-bromo-4-(1,2-diphenylvinyl)benzene.(San-Br):

[0045] Add 6.33g (0.05mol) of benzyl chloride and 24.92g (0.15mol) of triethyl phosphite into a 500ml three-necked flask, magnetically stir and flow argon, heat and reflux in an oil bath at 150°C for 24h, cool to room temperature, and pour Add 300ml of tetrahydrofuran (THF) into the three-neck flask, then add 8.42g of potassium tert-butoxide (t-BuOK0.075mol) and 10.44g of 4-bromobenzophenone (bis(4-bromophenyl)methanone, 0.04mol), and stir magnetically for 24h. After the reaction stopped, the reaction solution was poured into water for extraction, and a large amount of white precipitates precipitated out. Filtered with a funnel, the precipitates were collected, washed with ethanol for 3 times, and dried in vacuum at 60°C for 24 hours to obtain a white intermediate product ...

Embodiment 3

[0056] N1-(4-aminophenyl)-N1-(4'-(1,2,2-triphenylvinyl)biphenyl-4-yl)benzene-1,4-diamine(SiPAP-2NH 2 ) together

[0057] (1) Synthesis of intermediate 1-bromo-4-(1,2,2-triphenylvinyl)benzene.(Si-Br):

[0058] Add 16.7mL (0.1mol) of diphenylmethane (diphenylmethane) and 300ml of tetrahydrofuran (THF) into a 500ml three-necked flask, magnetically stir and pass argon, and after 40min of ice-salt bath, add 54.5mL (0.12mol ) n-butyllithium solution, after continuing the ice-salt bath for 40min, add 13.0555g4-bromobenzophenone (bis(4-bromophenyl)methanone, 0.05), after reacting at room temperature for 12h, add 250ml saturated ammonium chloride ( NH 4 Cl) solution, after stirring for 10 minutes, pour the reaction solution into a separatory funnel, take its upper layer, and use 300g of anhydrous sodium sulfate to absorb the water in the solution, add it to a three-necked bottle after suction filtration, use 200ml of toluene as a solvent, and magnetically stir And pass argon, heat...

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Abstract

The invention discloses a novel diamine compound, and a preparation method and an application thereof. The preparation method of the novel functional diamine compound comprises the following steps: a large conjugate structure comprising benzophenone carbonyl group is obtained; the ketone carbonyl group is subjected to a Wittig or Wittig-Horner reaction, such that a large conjugate system with a triphenylethylene/tetraphenylethylene structure and comprising a halogen atom is obtained; the halogen atom is further subjected to a Suzuki reaction or a plurality steps of reactions, such that a monoamine compound comprising a triphenylethylene/tetraphenylethylene large conjugate system is obtained; the monoamine compound is subjected to a reaction with halogenated nitrobenzene, such that a dinitro monomer comprising triphenylamine and the triphenylethylene/tetraphenylethylene large conjugate system is obtained; and the dinitro monomer is reduced into the novel diamine compound, such that the novel functional diamine compound comprising triphenylamine and a triphenylethylene/tetraphenylethylene structure is obtained. The synthesis method provided by the invention is simple. Purification is easy. The method is suitable for industrial productions. The synthesized diamine compound has a significant aggregation-induced emission property, and can be used for synthesizing high-performance and functional polymers such as polyamide, polyimide, polyamideimide, polyesterimide, and the like.

Description

technical field [0001] The invention relates to the field of material science, especially a novel functional diamine containing triphenylamine and triphenylethylene / tetraphenylethylene structure for the synthesis of high-performance functionalized polymers (especially polymers with low dielectric constants) Compounds and methods for their preparation. technical background [0002] Polyimide is one of the best heat-resistant varieties among engineering plastics that have been industrialized at present. It has outstanding properties unmatched by other materials, such as high mechanical strength, good high and low temperature resistance, excellent dielectric properties, and film-forming properties. OK wait. Since the development and industrialization of DuPont in the United States in the 1960s, it has been applied in various fields, especially in aerospace, aviation, microelectronics and military fields. [0003] With the rapid development of high-performance large-scale inte...

Claims

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Application Information

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IPC IPC(8): C07C211/54C07C217/92C07C213/02C07C209/36C07C209/68C09K11/06C08G73/10C08G73/14C08G73/16C08G69/26
Inventor 张艺刘亦武许家瑞吴欣慧石杰刘四委池振国
Owner SUN YAT SEN UNIV
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