Novel function diamine monomer containing carbazole and large conjugated structure and preparation method and application thereof

A conjugated structure, diamine monomer technology, applied in the field of material science, can solve problems such as performance needs to be further improved, single variety, etc., and achieve the effects of high yield, easy purification, and simple synthesis process

Inactive Publication Date: 2012-11-07
SUN YAT SEN UNIV
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Problems solved by technology

In the past two years, soluble functionalized polyimide based on triphenylamine structure has shown attractive application prospects in the application of polymer storage materials due to its unique resistance switching effect, which has aroused the interest of researchers in this field. It is important to note that the focus of this system research is the design and synthesis of diamine monomers containing triphenylamine structure. However, at present, its variety is relatively single, and its performance needs to be further improved. Therefore, it is necessary to carry out the design and synthesis of new functional diamine monomers. Research

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  • Novel function diamine monomer containing carbazole and large conjugated structure and preparation method and application thereof
  • Novel function diamine monomer containing carbazole and large conjugated structure and preparation method and application thereof
  • Novel function diamine monomer containing carbazole and large conjugated structure and preparation method and application thereof

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preparation example Construction

[0028] Wherein, the preparation method of the novel functional diamine monomer containing carbazole and large conjugated structure as shown in general structural formula I or II comprises the following steps:

[0029] (1) Use the active hydrogen in the dihalogenated carbazole monomer carbazole to graft a large conjugated structure to obtain a large conjugated system monomer containing two halogen atoms. The large conjugated structure containing two halogen atoms has the following structural features:

[0030]

[0031] Where X can be fluorine, chlorine, bromine or iodine.

[0032] (2) Utilize p-aminophenylboronic acid to react with two halogen atoms of the macroconjugated system monomer containing two halogen atoms described in step (1) by Suzuki reaction to obtain the compound shown in general structural formula I or II A new functional diamine monomer with a carbazole structure and a large conjugated system.

[0033] The preparation method of the novel functional diamine...

Embodiment 1

[0046] N 1 -(4-(3,6-bis(4-(trifluoromethyl)phenyl)-9H-carbazol-9-yl)phenyl)-N 1 Synthesis of -(4-aminophenyl)benzene-1,4-diamine:

[0047]

[0048] (1) Synthesis of intermediate 3,6-dibromo-9-(4-nitrophenyl)-9H-carbazole:

[0049] 32.5g (0.1mol) of 3,6-dibromocarbazole (3,6-dibromo-9H-carbazole), 11.2g (0.3mol) of potassium tert-butoxide (t-BuOK) and 21.165g (0.10mol) of Add fluoronitrobenzene (1-fluoro-4-nitrobenzene) into a 500ml three-necked flask, use N,N-dimethylformamide (DMF) as a solvent, stir magnetically and pass argon gas, heat and reflux in an oil bath at 100°C for 64h , the reaction solution was poured into ice water, suction filtered to obtain a khaki solid, and the yellow solid was recrystallized to obtain a light yellow crystal, which was dried in vacuo to obtain a khaki intermediate product 3,6-dibromo-9-(4-nitrophenyl )-9H-carbazole 41.5g.

[0050] (2) Synthesis of 9-(4-nitrophenyl)-3,6-bis(4-(trifluoromethyl)phenyl)-9H-carbazole:

[0051] 8.9218g (0....

Embodiment 2

[0059] N 1 -(4-(3,6-bis(4-fluorophenyl)-9H-carbazol-9-yl)phenyl)-N 1 Synthesis of -(4-aminophenyl)benzene-1,4-diamine:

[0060]

[0061] (1) Synthesize the intermediate 3,6-dibromo-9-(4-nitrophenyl)-9H-carbazole according to Example 1;

[0062] (2) Synthesis of 4-(3,6-dibromo-9H-carbazol-9-yl)benzolamine:

[0063] Add 32.5g (0.1mol) of 3,6-dibromo-9-(4-nitrophenyl)-9H-carbazole into a 250ml three-necked flask, add 150ml of absolute ethanol, magnetically stir and argon, and heat the oil bath to 70°C Finally, add 10%wt palladium carbon 0.2g, and gradually drop 50ml hydrazine hydrate, after reflux reaction 10h, suction filtration after cooling, collect beige solid, obtain beige product 4-(3 ,6-dibromo-9H-carbazol-9-yl)benzonamine 39.9g.

[0064] (3) Synthesis of intermediate N-(4-(3,6-dibromo-9H-carbazol-9-yl)phenyl)-4-nitro-N-(4-nitrophenyl)benzonamine:

[0065] 41.611g (0.1mol) 4-(3,6-dibromo-9H-carbazol-9-yl) benzonamine, 45.574g (0.03mol) cesium fluoride (CsF) and 42....

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Abstract

The invention discloses a novel function diamine monomer containing carbazole and a large conjugated structure and a preparation method and application thereof. The novel function diamine monomer is started from a basic monomer element and obtained through a series of chemical reaction of helogenation reaction, Wittig-Horner reaction, UIImann reaction, Suzuki reaction and the like. A synthetic method of the novel function diamine monomer is simple in process, easy to purify and suitable for industrial production. The monomer has a large non-planar large conjugated structure, has the effect of aggregation-induced emission, and can be used for synthetizing high-performance functionalized polymers of polyamide, polyimide, polyamide-imide, polyester-imide and the like.

Description

technical field [0001] The invention relates to the field of material science, in particular to a novel functional diamine monomer containing carbazole and a large conjugated structure and a preparation method thereof. This monomer can be used to synthesize high-performance functionalized polymers. 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. Since polyimide is generally insoluble in organic solvents, it is usually processed with a precursor polyamic acid with good s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C08G69/00C08G73/10C08G73/14C08G73/16
Inventor 张艺刘亦武许家瑞兰麒刘四委池振国
Owner SUN YAT SEN UNIV
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