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A kind of diamine compound containing symmetrical double fluorophore structure and its preparation and application, polyamide and polyimide and its preparation and application

A technology of dual fluorophores and amine compounds, which is applied in the field of electronically controlled fluorescence, can solve the problems of long transition time, high oxidation potential, and low fluorescence contrast, and achieve the effects of enhanced dissolution and film-forming ability, enhanced fluorescence intensity, and high fluorescence contrast

Active Publication Date: 2022-07-22
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the lack of resonantly stable N atoms, the reported synthesized monotriphenylamine structure has a high oxidation potential (>1.0V) and is prone to side reactions, so the electrochemical stability is low.
In addition, when a single fluorophore is linked to triphenylamine, the strong π-π stacking effect between molecules leads to low fluorescence contrast and long transition time, which limits its practical application.

Method used

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  • A kind of diamine compound containing symmetrical double fluorophore structure and its preparation and application, polyamide and polyimide and its preparation and application
  • A kind of diamine compound containing symmetrical double fluorophore structure and its preparation and application, polyamide and polyimide and its preparation and application
  • A kind of diamine compound containing symmetrical double fluorophore structure and its preparation and application, polyamide and polyimide and its preparation and application

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preparation example Construction

[0029] The present invention provides a method for preparing a diamine compound containing a symmetrical double fluorophore structure according to the above technical solution, comprising the following steps:

[0030] Mixing p-phenylenediamine, p-fluoronitrobenzene, a first catalyst and an organic solvent to carry out a substitution reaction to obtain a dinitro monomer;

[0031] Mixing the dinitro monomer, the brominated fluorescent compound, the second catalyst and the polar solvent, and carrying out a coupling reaction to obtain a dinitro compound;

[0032] The dinitro compound, the third catalyst, the reducing agent and the mixed solvent are mixed, and a reduction reaction is carried out to obtain the diamine compound containing the symmetrical double fluorophore structure of the structure shown in formula I;

[0033] The dinitro monomer has the structure shown in formula II-1:

[0034]

[0035] The structural formula of the brominated fluorescent compound is Br-R;

[...

Embodiment 1

[0099] The preparation of monomer N,N'bis(4-nitrophenyl)-1,4-p-phenylenediamine, its structure is:

[0100]

[0101] Under nitrogen conditions, add 21.6g (200mmol) of p-phenylenediamine, 64.9g (460mmol) of p-fluoronitrobenzene, 101.2g (1000mmol) to the 1000mL there-necked flask equipped with a mechanical stirring device, a thermometer and a condenser tube. Triethylamine and 45.1 g (140 mmol) of tetrabutylammonium bromide, then 424 mL of sulfolane was added, the solid content of the obtained system was 30.3 wt%, and the reaction was carried out at 180 ° C under microwave conditions for 7 h, and the obtained product system was cooled to room temperature and then discharged. In 2000mL of ice water, suction filtration and drying to obtain a reddish-brown crude material, the obtained crude material is recrystallized three times with a DMSO / ethanol solution with a volume ratio of 1:3 to obtain 29.4g of purple-red N,N'-bis(4- Nitrophenyl)-1,4-p-phenylenediamine powder, 42% yield. ...

Embodiment 2

[0107] The preparation of diamine monomer N,N'-bis(4-aminophenyl)-N,N'-bis(9,9 spirobifluorenyl)-1,4-p-phenylenediamine, its structure is:

[0108]

[0109] Under a nitrogen atmosphere, 4.2g (12mmol) N,N'-bis(4-nitrophenyl)-1,4 prepared in Example 1 was added to a 250mL three-necked flask with a mechanical stirring device, a thermometer and a condenser tube. - p-phenylenediamine, 9.8g (24.8mmol) 2-bromo-9,9'spirobis(9H-fluorene), 3.8g (60mmol) copper powder, 13.2g (96mmol) potassium carbonate and 1.9g (7.2mmol) 18 crown ether-6, then add 50mL o-dichlorobenzene, the solid content of the obtained system is 33.5wt%, react at 160 ° C for 24h, filter while hot to remove copper powder and salt, remove the filtrate by vacuum distillation, and use the volume ratio of 2:1 dichloromethane / petroleum ether was used as a developing solvent to carry out column chromatography to obtain 6.1 g of orange-yellow dinitro compound with a yield of 52.0%;

[0110] Under nitrogen protective atmos...

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Abstract

The invention provides a diamine compound containing a symmetrical double fluorophore structure, preparation and application thereof, polyamide and polyimide, and preparation and application thereof, belonging to the technical field of electronically controlled fluorescence. In the diamine compound structure provided by the present invention, a highly symmetrical bis-triphenylamine group is used as a derivative structure of triphenylamine, and the derivative structure of bis-triphenylamine can significantly enhance the resonant coupling between two N atoms. Stability, the more extended conjugation length phase makes it have a higher HOMO energy level and lower oxidation potential than monotriphenylamine, which significantly enhances the electrochemical stability. In addition, the polymer prepared by the diamine compound has high fluorescence contrast and short fluorescence switching time.

Description

technical field [0001] The invention relates to the technical field of electronically controlled fluorescence, in particular to a diamine compound containing a symmetrical double fluorophore structure, preparation and application thereof, polyamide and polyimide, and preparation and application thereof. Background technique [0002] Electronically controlled fluorescence refers to the phenomenon that the fluorescence of a material is reversibly switched or discolored under the action of an external electric field. Because of its advantages of good controllability, good reversibility and environmental friendliness, it is used in the fields of optical display, information encryption and information communication. Has potential application value. [0003] Polymers have greater advantages due to their strong processability and easy structure modification. Polyamides and polyimides have excellent physical and chemical properties. The introduction of star-shaped triphenylamine (TP...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/61C07C209/36C07C211/58C07C213/00C07C217/94C09K11/06C08G69/26C08G69/32C08G73/10
CPCC07C211/61C07C211/58C07C217/94C09K11/06C08G69/26C08G69/32C08G73/1078C08G73/1067C08G73/1039C09K2211/1011C09K2211/1007
Inventor 王大明李晓倩苏凯欣赵晓刚周宏伟陈春海
Owner JILIN UNIV
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