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Novel functional triamine monomer containing carbazole structure and preparation method and application thereof

A technology of triamine monomers and monomers, applied in the field of material science, to achieve the effects of high yield, easy purification, and simple synthesis process

Inactive Publication Date: 2016-06-01
HUNAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing research is limited to linear polyimides containing carbazole structures, and there is no report on hyperbranched polyimides containing carbazole structures.

Method used

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  • Novel functional triamine monomer containing carbazole structure and preparation method and application thereof
  • Novel functional triamine monomer containing carbazole structure and preparation method and application thereof
  • Novel functional triamine monomer containing carbazole structure and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthesis of 9-(3-aminophenyl)-9H-carbazole-3,6-diamine:

[0031]

[0032] (1) Synthesis of intermediate 3,6-dinitro-9H-carbazole:

[0033] Combine 4.180g (0.025mol) 9H-carbazole, 7.000g (0.030mol) Cu(NO 3 ) 2 ·2.5H 2 O, 20ml acetic acid, and 30ml acetic anhydride were added to a 500ml three-necked flask and stirred at room temperature for 30min. The temperature was raised to 100°C for 30 minutes. Then add 10ml of acetic acid and 250ml of water, filter the reaction solution with suction, and wash the filter cake five times in 100ml of distilled water; then dissolve the filter cake in a mixed solution of 20gKOH, 250ml of water and 250ml of ethanol, continue to stir for 30min and then pump filter. The filtrate was acidified with concentrated hydrochloric acid and left to stand for 30 min. The yellow precipitate was collected by suction filtration. The product was purified by column chromatography with dichloromethane: n-hexane=1:2 (volume ratio) as the mobile phase and silic...

Embodiment 2

[0041] N 1 -(4-(3-amino-9H-carbazol-9-yl)phenyl)-N 1 -(4-aminophenyl)benzene-1,4-diamine synthesis:

[0042]

[0043] (1) Synthetic intermediate 9-(4-nitrophenyl)-9H-carbazole:

[0044] Add 1.672g (0.01mol) carbazole, 2.122ml (0.02mol) p-fluoronitrobenzene and 50ml DMF into a 100ml three-necked flask, stir magnetically and ventilate with argon, then add 1.122g (0.01mol) potassium tert-butoxide, The temperature was raised to 110°C for 24h. The reaction solution was poured into ice water, the precipitate was filtered out and crystallized twice with ethanol, and the filter cake obtained by suction filtration was dried at 80° C. under vacuum for 24 hours to obtain 2.566 g of the product with a yield of 89%. The intermediate structure is as follows:

[0045]

[0046] (2) Synthesis of intermediate 4-(9H-carbazol-9-yl)aniline:

[0047] Add 2.883g (0.01mol) 9-(4-nitrophenyl)-9H-carbazole into a 500ml three-necked flask, add 300ml absolute ethanol, magnetically stir and argon gas, after heat...

Embodiment 3

[0058] N 1 -(4-aminophenyl)-N 1 Synthesis of -(4-(3-(4-aminophenyl)-9H-carbazol-9-yl)phenyl)benzene-1,4-diamine:

[0059]

[0060] (1) Synthesis of intermediate 3-bromo-9-(4-nitrophenyl)-9H-carbazole:

[0061] Add 2.461g (0.01mol) 3-bromocarbazole, 2.122ml (0.02mol) p-fluoronitrobenzene and 50ml DMF into a 100ml three-necked flask, stir magnetically with argon, and then add 1.122g (0.01mol) tert-butanol Potassium, heated to 110 ℃ for 24h. The reaction solution was poured into ice water, the filter cake obtained by suction filtration was recrystallized twice with ethanol, and the precipitate was filtered out and dried under vacuum at 80° C. for 24 hours to obtain 3.158 g of the product with a yield of 86%. The intermediate structure is as follows:

[0062]

[0063] (2) Synthesis of intermediate 4-(3-bromo-9H-carbazol-9-yl)aniline:

[0064] Add 3.672g (0.01mol) 3-bromo-9-(4-nitrophenyl)-9H-carbazole to a 500ml three-necked flask, add 450ml absolute ethanol, magnetically stir and argon...

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Abstract

The invention discloses a novel functional triamine monomer containing a carbazole structure and a preparation method and application thereof. Starting from carbazole, the novel functional triamine monomer containing carbazole is prepared through a nitration reaction, a Ullmann coupling reaction, a reduction reaction and other reactions; or starting from mono-halogenated carbazole or dihalogenated carbazole, the novel functional triamine monomer containing carbazole is prepared through a Ullmann coupling reaction, a Suzuki reaction, a reduction reaction and other reactions. The novel functional triamine monomer containing carbazole is simple in synthesis method and technology, high in yield and easy to purify, and therefore the novel functional triamine monomer containing carbazole is suitable for industrial production. The novel functional triamine monomer can be used for synthesizing hyperbranched and functional polyamide, polyimide, polyamide imide, polyester imide and other polymers.

Description

Technical field [0001] The invention relates to the field of materials science, in particular to a novel functional triamine monomer containing a carbazole structure and a preparation method thereof. The monomer can be used to synthesize hyperbranched and functionalized polyamide, polyimide, polyamideimide and polyesterimide polymers. technical background [0002] Hyperbranched polyimides (HBPIs) have a series of unique physical and chemical properties due to the combination of the advantages of both hyperbranched polymers and polyimides, such as good solubility, no chain entanglement, difficult or non-crystalline, low Solution and melt viscosity, excellent heat resistance, solvent resistance and high dielectric properties have attracted the attention of the majority of scientific researchers in recent years. At present, hyperbranched polyimides are mainly used in membrane materials such as gas separation membranes and permeable membranes, as well as other high-tech fields such ...

Claims

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Application Information

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IPC IPC(8): C07D209/86C08G69/00C08G73/10C08G73/14C08G73/16
CPCC07D209/86C08G69/00C08G73/10C08G73/14C08G73/16
Inventor 谭井华熊宇风刘亦武黄杰赵胜球何伟林曾义
Owner HUNAN UNIV OF TECH
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