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Novel functional diamine monomer with large conjugate structure, and preparation method and application thereof

A technology of diamine monomer and conjugated structure, which is applied in the field of material science, can solve the problems of single species and performance to be further improved, and achieve the effects of high yield, easy purification and simple synthesis process

Active Publication Date: 2014-06-18
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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

Method used

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  • Novel functional diamine monomer with large conjugate structure, and preparation method and application thereof
  • Novel functional diamine monomer with large conjugate structure, and preparation method and application thereof
  • Novel functional diamine monomer with large conjugate structure, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] 4', 4 "-(2-phenylethene-1, 1-diyl) dibiphenyl-4-amine (TriPEDBA) synthesis:

[0022]

[0023] (1) Synthetic intermediate 4,4'-(2-phenylethene-1,1-diyl)bis(bromobenzene)(TriPEDBr):

[0024] Add 11.6ml (0.1mol) of benzyl chloride and 52.2ml (0.3mol) of triethyl phosphite into a 500ml three-neck flask, magnetically stir and pass argon, heat and reflux in an oil bath at 150°C for 24h, cool to room temperature, and pour Add 300ml tetrahydrofuran (THF) to the three-necked flask, then add 16.82g potassium tert-butoxide (t-BuOK 0.15mol) and 27.2g dibromobenzophenone (bis(4-bromophenyl)methanone 0.08mol), stir magnetically for 24h, and react After stopping, the reaction solution was poured into water for extraction, and a large amount of white precipitates precipitated out, filtered through a funnel, collected the precipitates, washed with ethanol three times, and dried in vacuum at 60°C for 10 hours to obtain 31.5 g of the white intermediate product TPEDBr. The rate is 95%....

Embodiment 2

[0029] 4 ', 4 "-(2,2-diphenylethene-1,1-diyl) dibiphenyl-4-amine (TetraPEDBA) synthesis:

[0030]

[0031] (1) Synthetic intermediate 4,4'-(2,2-diphenylethene-1,1-diyl)bis(bromobenzene)(TetraPEDBr):

[0032] Add 6.18ml (0.0368mol) of diphenylmethane (diphenylmethane) and 100ml of tetrahydrofuran (THF) into a 500ml three-necked flask, magnetically stir and pass argon, and after 40min of ice-salt bath, add 21.7ml (0.04784mol ) n-butyllithium solution, after continuing the ice-salt bath for 40min, add 10g of dibromobenzophenone (bis(4-bromophenyl)methanone 0.0217mol), after reacting at room temperature for 12h, add 100ml of saturated ammonium chloride (NH 4 Cl) solution, after stirring for 10min, the reaction solution was poured into a separatory funnel, the upper layer was taken, and the water in the solution was adsorbed with 150g of anhydrous sodium sulfate, added to a three-necked flask after suction filtration, and 100ml of toluene was used as a solvent, magnetically stir...

Embodiment 3

[0037] 4,4′-(4′,4″-(2-phenylethene-1,1-diyl)bis(biphenyl-4′,4-diyl))bis(oxy)dibenzonamine (TriPEDOBA) synthesis:

[0038]

[0039] (1) Synthetic intermediate 4′, 4″-(2-phenylethene-1, 1-diyl)dibiphenyl-4-ol (TriPEDO):

[0040] First, TriPEDBr was synthesized according to Example 1. Weigh 6.0318g (0.015mol) of TriPEDBr and 4.1379g (0.03mol) of p-hydroxyphenylboronic acid (4-hydroxyphenylboronic acid) into a 500ml three-necked flask, add 100ml of tetrahydrofuran, then add 45ml of 2mol / L potassium carbonate solution, and stir magnetically And pass argon, heat the oil bath to 70°C, add 0.05g tetrakistriphenylphosphine palladium, reflux reaction for 24 hours, pour the reaction solution into water for extraction, a large amount of white precipitates precipitate out, filter with a funnel, collect the precipitates , washed 3 times with ethanol, dried to obtain off-white product 5.4g, productive rate is 84%, and its structural formula is as follows:

[0041]

[0042] (2) Synthe...

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Abstract

The invention discloses a novel functional diamine monomer with a large conjugate structure, and a preparation method and application thereof. In the novel functional diamine monomer, ketone carbonyl is converted into double bonds by utilizing dihalogenated benzophenone in a Wittig or Wittig-Horner reaction to form an aromatic dibromo-monomer; and substituted halogen atoms are linked with other chemical groups by one or more than one step of a reaction so as to obtain the novel functional diamine monomer with the large conjugate structure. The synthetic method is simple, and the novel functional diamine monomer is easy to purify, so the novel functional diamine monomer is suitable for industrial production; and the synthesized compound has the obvious performance of aggregation-induced luminescence. The diamine monomer of the invention can be used for synthesizing high-performance and functional polymers such as polyamides, polyimides, polyamide imides, polyester imides and the like.

Description

technical field [0001] The invention relates to the field of material science, in particular to a novel functional diamine monomer with a large conjugated structure for synthesizing high-performance functionalized polymers and a preparation method thereof. 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 solubility, and then undergoes dehydration an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/50C07C209/10C07C217/90C07C213/02C08G69/00C08G73/10
Inventor 张艺刘亦武李海银兰麒李依虹秦泽鑫刘四委池振国许家瑞
Owner SUN YAT SEN UNIV
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