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Diamine compound containing diarylamine-pyrene structure, and preparation method thereof, polyamide, polyimide and applications thereof

A technology of amine compounds and polyimides, applied in the field of electronically controlled fluorescence, which can solve the problems of low solid-state fluorescence intensity and reduced stability

Active Publication Date: 2020-03-24
JILIN UNIV
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  • Abstract
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  • Application Information

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Problems solved by technology

For example, the polyamide film prepared by Liu Guisheng's research group through 4-(bis(4-aminophenyl)amino)benzonitrile and cyclohexanedioic acid has high fluorescent switch contrast in the visible light region, but due to high oxidation Potential makes it less stable
Another example is the use of N,N'-bis(4-aminophenyl)-N,N'-bis(4-methoxyphenyl)-2,7-diamine-9,9-diamine by the research group of Mr. Chen Chunhai The polyamide membrane prepared by methylfluorene and 1,4-cyclohexanedioic acid can still maintain excellent stability after 1000 switching cycles, but the solid-state fluorescence intensity is very low due to the aggregation quenching effect
In summary, although electronically controlled fluorescent materials of polymers have been developed vigorously, most polymer materials cannot simultaneously possess comprehensive excellent properties, including easy processing, high fluorescence on / off contrast, high quantum efficiency of solid-state fluorescence, and stable cycling. Excellent performance and fast response, which limit its application

Method used

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  • Diamine compound containing diarylamine-pyrene structure, and preparation method thereof, polyamide, polyimide and applications thereof
  • Diamine compound containing diarylamine-pyrene structure, and preparation method thereof, polyamide, polyimide and applications thereof
  • Diamine compound containing diarylamine-pyrene structure, and preparation method thereof, polyamide, polyimide and applications thereof

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preparation example Construction

[0039] The present invention also provides the preparation method of the diamine compound containing bisarylamine-pyrene structure described in the above technical scheme, comprising the following steps:

[0040] (1) After mixing p-fluoronitrobenzene, 4-methoxyaniline, triethylamine and solvent, in a protective atmosphere, carry out nucleophilic substitution reaction to obtain 4-nitro-4'-methoxydiphenylamine ;

[0041] (2) After mixing the 4-nitro-4'-methoxydiphenylamine, 1,6-dibromopyrene, potassium carbonate, copper powder, 18-crown-6 and solvent, in a protective atmosphere, Carry out the Ullmann reaction to obtain two (4-nitrophenyl)-bis(4'-methoxyphenyl)-1,6-diaminopyrene;

[0042] (3) Mix the bis(4-nitrophenyl)-bis(4'-methoxyphenyl)-1,6-diaminopyrene, Pd / C catalyst and solvent, and heat to 70-90°C , and then adding hydrazine hydrate for reduction reaction to obtain a diamine compound containing a bisarylamine-pyrene structure.

[0043] In the invention, after mixing p-...

Embodiment 1

[0121] 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'-methoxy-diphenylamine, the yield is 82.1%;

[0122] 40g (163.8mmoL) of 4-nitro-4'-methoxy-diphenylamine, 23.59g (65.52mmoL) of 1,6-dibromopyrene, 33.31g (524.2mmoL) of copper powder, 72.45g (524.2mmoL) ) of potassium carbonate, 22.51g (85.18mmoL) of 18-crown-6 and 196mL of o-dichlor...

Embodiment 2

[0128] With 0.6268g (1mmoL) two (4-aminophenyl)-two (4'-methoxyphenyl)-1,6-diaminopyrene (prepared by Example 1), 0.1722g (1mmoL) 1, 4-Cyclohexanedioic acid, 0.2397g CaCl 2 , 1.6mL triphenyl phosphite, 3.8mL pyridine and 3.1mL N-methylpyrrolidone were mixed, and reacted at 110°C for 3.5h under a nitrogen atmosphere; after the reaction was completed, cooled to room temperature, and discharged into 100mL ethanol , and then filtered to obtain a yellow fibrous substance; the obtained yellow fibrous substance was washed with ethanol, water, and ethanol in turn for 30 minutes, and then dried in a vacuum oven at 90°C to obtain 1,4-cyclohexanedioic acid poly Amide, the mass is 0.7802g.

[0129] Test the infrared spectrum of the product obtained in this embodiment, the results are as follows figure 2 shown. Among them, 3304cm -1 N-H stretching vibration absorption peak, 1660cm -1 It is the C=O stretching vibration absorption peak, indicating that the polyamide obtained in this ex...

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Abstract

The invention provides a diamine compound containing a diarylamine-pyrene structure, and a preparation method thereof, polyamide, polyimide and applications thereof, and belongs to the technical fieldof electronic control fluorescence. According to the invention, the diamine compound containing the diarylamine-pyrene structure is named di(4-aminophenyl)-di(4'-methoxyphenyl)-1,6-diaminopyrene, andhas a structure represented by a formula I; by combining diphenylamine and pyrene, a diarylamine-pyrene structure is constructed, and is a compound represented by the formula I; and in a material prepared from the compound, the electron donating group diphenylamine can be used as an auxochrome of pyrene to enhance the fluorescence intensity of the material, the twisted diphenylamine can weaken the accumulation effect, enhance the solubility and the solid state fluorescence of the material and accelerate the response speed of electronic control fluorescence, and by introducing an electron-donating methoxy substituent group into the para-position of diphenylamine, the oxidation potential can be effectively reduced, and the electrochemical stability is improved.

Description

technical field [0001] The invention relates to the technical field of electronically controlled fluorescence, in particular to a diamine compound containing a bisarylamine-pyrene structure and a preparation method thereof, a polyamide and a polyimide and applications thereof. Background technique [0002] Electronically controlled fluorescence refers to the reversible response of the fluorescence of materials to electrochemical redox reactions. It has good application prospects in the fields of optical display, information encryption and sensing, and has attracted widespread attention from scholars. At present, electronically controlled fluorescent materials are mainly divided into three categories: inorganic composite materials, small molecule electroactive fluorophores, and polymer materials. Among them, polymeric materials stand out due to their excellent processability and structural variability. For example, the polyamide film prepared by Liu Guisheng's research group...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/84C07C213/02C08G69/32C08G69/26C08G73/10C09K11/06
CPCC07C217/84C08G69/26C08G69/32C08G73/1067C09K11/06C09K2211/1416C09K2211/1425C09K2211/1433C09K2211/1466
Inventor 陈春海阎志华苏凯欣周宏伟王大明赵晓刚
Owner JILIN UNIV
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