A diamine compound containing bis(diphenylamine)-tetraphenylethylene structure and its preparation method, a polyamide and its preparation method

An amine compound and tetraphenylethylene technology, which is applied in the field of electronically controlled fluorescence, can solve problems such as limited application, and achieve the effects of short response time, improved ion doping rate, and good cycle stability.

Active Publication Date: 2021-02-26
JILIN UNIV
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  • Abstract
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  • Application Information

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Problems solved by technology

[0003] However, many electronically controlled fluorescent polymers currently synthesized can emit bright fluorescence in the solution state, but in the solid state, the fluorescence is quenched due to the strong π-π stacking effect between molecules, that is, the ACQ (aggregation-caused quenching) effect occurs. Limit their applications in some fields such as organic light-emitting diodes, fluorescent sensors, etc.

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  • A diamine compound containing bis(diphenylamine)-tetraphenylethylene structure and its preparation method, a polyamide and its preparation method
  • A diamine compound containing bis(diphenylamine)-tetraphenylethylene structure and its preparation method, a polyamide and its preparation method
  • A diamine compound containing bis(diphenylamine)-tetraphenylethylene structure and its preparation method, a polyamide and its preparation method

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preparation example Construction

[0050] The present invention also provides the preparation method of the diamine compound containing bis(diphenylamine)-tetraphenylethylene structure described in the above technical scheme, comprising the following steps:

[0051] (1) In a protective atmosphere, 4-halogenated nitrobenzene, Carry out nucleophilic substitution reaction with basic catalyst in polar organic solvent to obtain diphenylamine derivatives;

[0052] said where R is -CH 3 、-OCH 3 、-OCH 2 CH 3 , -N(CH 3 ) 2 or -C(CH 3 ) 3 ;

[0053] The diphenylamine derivative has a structure shown in formula II:

[0054]

[0055] (2) In a protective atmosphere, the diphenylamine derivatives obtained in the step (1), 1,1-diphenyl-2,2-bis(4-halogenated phenyl)ethene derivatives and catalysts in aromatic hydrocarbon Carry out coupling reaction in the solvent, obtain dinitro compound, described dinitro compound has the structure shown in formula III:

[0056]

[0057] (3) carry out reduction reaction wi...

Embodiment 1

[0088] Mix 40g (324.8mmoL) of p-methoxyaniline, 35.2540g (249.9mmoL) of p-fluoronitrobenzene, 32.8672g (324.8mmoL) of triethylamine and 273mL of dimethyl sulfoxide, stir and nitrogen Under protected conditions, react at 85°C for 36 hours; after the reaction is completed, cool to room temperature, discharge the material in ice water, stir well, and filter to obtain the crude product; mix the crude product with N,N-dimethylacetamide and ethanol (Volume ratio 1:2) was prepared into a hot saturated solution, the temperature of the hot saturated solution was 90°C, then naturally cooled to room temperature, filtered, and the resulting solid was vacuum-dried at 80°C to obtain 50.1 g of orange 4-nitro- 4'-methoxyl-diphenylamine, yield rate is 82.1%, the structural formula of 4-nitro-4'-methoxyl-diphenylamine is as follows:

[0089]

[0090] 40g (163.8mmoL) of 4-nitro-4'-methoxy-diphenylamine, 34.65g (70.68mmoL) of 1,1-diphenyl-2,2-bis(4-bromophenyl)ethylene, Mix 36.19g (565.4mmoL)...

Embodiment 2

[0101] 45g (301.5mmoL) of 4-tert-butylaniline, 37.4966g (251.25mmoL) of p-fluoronitrobenzene, 30.5088g (301.5mmoL) of triethylamine and 308mL of dimethyl sulfoxide were mixed, stirring and Under the condition of nitrogen protection, react at 85°C for 36h; after the reaction is completed, cool to room temperature, discharge the material in ice water, stir well, and filter to obtain the crude product; the crude product is mixed with N,N-dimethylacetamide and Ethanol (volume ratio 1:2) was prepared into a hot saturated solution, the temperature of the hot saturated solution was 90°C, then naturally cooled to room temperature, filtered, and the resulting solid was vacuum-dried at 80°C to obtain 58.0 g of orange 4-nitro -4'-tert-butyl-diphenylamine, the productive rate is 85.4%, the structural formula of 4-nitro-4'-tert-butyl-diphenylamine is as follows:

[0102]

[0103] 40g (147.0mmoL) of 4-nitro-4'-tert-butyl-diphenylamine, 32.05g (65.37mmoL) of 1,1-diphenyl-2,2-bis(4-bromoph...

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Abstract

The present invention relates to the field of electronically controlled fluorescence technology, and provides a diamine compound containing a bis(diphenylamine)-tetraphenylethylene structure. The diamine compound has a structure shown in formula I. The diamine compound provided by the present invention has " 2,2-triphenylamine-tetraphenylethylene” structure, in the polyamide prepared from the diamine compound, the tetraphenylethylene group with aggregation-induced emission effect makes the polyamide have excellent characteristics of bright fluorescence in the solid state, and The polyamide has a higher fluorescence quantum yield; at the same time, the star-shaped tetraphenylethylene and triphenylamine structures in the polyamide can weaken the close packing of the polyamide molecular chain, improve the ion doping rate, and shorten the electrical control of the polymer. Fluorescence response time; In addition, the introduction of electron-pushing groups at the para-position of triphenylamine can effectively reduce the oxidation potential and improve the electrochemical stability of polyamides.

Description

technical field [0001] The invention relates to the technical field of electronically controlled fluorescence, in particular to a diamine compound containing a bis(diphenylamine)-tetraphenylethylene structure and a preparation method thereof, a polyamide and a preparation method thereof. Background technique [0002] Electronically controlled fluorescence refers to the phenomenon of reversible fluorescent switching or discoloration of materials under the action of an applied voltage. Materials with electrically controlled fluorescent properties have great application prospects in sensors, monitoring electrode surfaces, and new fluorescent displays. Compared with inorganic composite materials and small molecules, polymers have greater advantages due to their good processability and easy structure modification. [0003] However, many electronically controlled fluorescent polymers currently synthesized can emit bright fluorescence in the solution state, but in the solid state, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C217/84C07C211/55C07C213/08C07C211/56C07C209/10C07C209/32C08G69/40C08G69/32C08G69/26C08G69/42C09K11/06G01N27/26G01N21/64
CPCC07C209/10C07C209/325C07C211/55C07C213/08C07C217/84C08G69/26C08G69/32C08G69/40C08G69/42C09K11/06C09K2211/1433G01N21/64G01N27/26C07C211/56
Inventor 赵晓刚李晓倩苏凯欣姚佳楠王大明周宏伟陈春海
Owner JILIN UNIV
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