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A kind of diamine compound containing three n centers, preparation method and application thereof, polyamide and preparation and application thereof

A technology of amine compounds and polyamides, applied in the field of polyamides and its preparation and application, can solve the problems of unfavorable electrochemical stability, poor electrical activity, high oxidation potential of single cation radicals, etc.

Active Publication Date: 2022-07-08
JILIN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in the currently disclosed polymers containing p-phenylenediamine structures, the oxidation potential for forming monocation radicals is still high, and the dications are unstable, which makes their electroactivity poor at high voltages, which is not conducive to electrocatalysis. Chemical stability, and both monotriphenylamine and p-phenylenediamine can only achieve double or triple color changes, which is not conducive to the development and utilization of multicolor optoelectronic materials

Method used

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  • A kind of diamine compound containing three n centers, preparation method and application thereof, polyamide and preparation and application thereof
  • A kind of diamine compound containing three n centers, preparation method and application thereof, polyamide and preparation and application thereof
  • A kind of diamine compound containing three n centers, preparation method and application thereof, polyamide and preparation and application thereof

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preparation example Construction

[0023] The present invention provides the preparation method of the diamine compound containing three N centers described in the above technical scheme, comprising the following steps:

[0024] Mixing p-halogen nitrobenzene, N,N-dimethyl-p-phenylenediamine, a basic catalyst and a first polar solvent, and carrying out a first substitution reaction to obtain the diphenylamine derivative of the structure shown in formula II;

[0025] Mixing the diphenylamine derivative, the brominated fluorophore compound, the copper catalyst, the co-catalyst, the phase transfer catalyst and the second polar solvent to carry out a coupling reaction to obtain the mononitro compound of the structure shown in formula III;

[0026] Mixing the mononitro compound, the palladium carbon catalyst, the hydrazine hydrate and the first mixed solvent to carry out the first reduction reaction to obtain the monoamino compound of the structure shown in formula IV;

[0027] Mixing the monoamino compound, p-haloge...

Embodiment 1

[0082] Preparation of 4-N,N-dimethyl-4'nitrodiphenylamine:

[0083]Under nitrogen protection, add 27.2g (200mmol) of N,N-dimethyl-p-phenylenediamine, 25.4g (180mmol) of p-fluoronitrobenzene and 18.2g (180mmol) of triethylamine into a 500mL there-necked flask, add 200mL DMSO, the solid content of the mixed system was 24.3wt%, reacted at 85°C for 20 hours, discharged into ice water, dried to obtain dark red solid crude material, and the crude material was mixed with ethanol and DMF with a volume ratio of 4:1 The liquid was recrystallized to obtain 42 g of purple crystals with a yield of 91%. The structural formula is:

[0084]

[0085] Under nitrogen protection, 14.9 g (58.0 mmol) of the 4-N,N-dimethyl-4'nitrodiphenylamine, 10.0 g (48.3 mmol) 2-bromonaphthalene, 46.0 g (241.5 mmol) of the iodinated Cuprous, 69.2g (193.2mmol) of cesium carbonate and 12.2g (33.8mmol) of dibenzo-18-crown ether-6 were added in a 500mL there-necked flask, 227mL of dichlorotoluene was added, and t...

Embodiment 2

[0093] Under nitrogen protection, 10.4g (40.5mmol) of 4-N,N-dimethyl-4'nitrodiphenylamine prepared in Example 1, 8.0g (33.7mmol) of 2-bromo-6methoxynaphthalene, 10.7 g (168.5 mmol) of copper powder, 18.6 g (134.8 mmol) of potassium carbonate and 5.3 g (20.2 mmol) of 18-crown-6 were added to a 250 mL three-necked flask, 75.0 mL of dichlorotoluene was added, and the solid content of the mixed system was 36wt%, react at 175°C for 20h, filter while hot to obtain a filtrate, remove the dichlorotoluene solution by distillation under reduced pressure, and use a dichloromethane / petroleum ether developing agent with a volume ratio of 2.5:1 to carry out the column layer of the solid crude material. analytical and purification to obtain 9.3 g of a red mononitro compound 4-nitrophenyl-4-N,N dimethylphenyl-2-amino-2-bromo-6-methoxynaphthalene with a yield of 56.0% , the structure is as follows:

[0094]

[0095] Under nitrogen protection, in a 250mL there-necked flask, 8.0g (19.3mmol) ...

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Abstract

The invention provides a diamine compound containing three N centers, a preparation method and application thereof, a polyamide and the preparation and application thereof, belonging to the technical field of optoelectronic materials. The diamine compound of the present invention contains three N-atom electroactive centers and a high-efficiency fluorophore R, and the three N atoms can not only impart multiple electrochromic behaviors to the polymer prepared from the diamine compound, but also form a structure with the benzene ring. The resulting bis-p-phenylenediamine structure can also effectively stabilize cationic radicals. N,N-dimethyl is not only the third N atom center provider, but also acts as a strong electron donating group, which can effectively reduce the oxidation potential of the polymer. , so that the polymer has good electrochemical stability. The synergistic effect of high-efficiency fluorophore and propeller-type triphenylamine construction can make the polymer have high fluorescence contrast, and at the same time improve the stacking mode of the polymer, so that the polymer has good solubility while maintaining its own inherent thermal stability.

Description

technical field [0001] The invention relates to the technical field of optoelectronic materials, in particular to a diamine compound containing three N centers, a preparation method and application thereof, and a polyamide and preparation and application thereof. Background technique [0002] Electronically controlled fluorescence refers to the phenomenon that the fluorescence of a material undergoes reversible switching or discoloration under the action of an external electric field. Electrochromic material refers to the stable and reversible change of its optical properties (absorption, transmission and reflection) under the action of an external electric field, and the macroscopic performance is the change of color and transparency. Fluorescence signals are generally detected in a dark background, and have the characteristics of low noise, high sensitivity and low detection limit. Combined with electrochemistry, they have great development prospects in sensors, monitoring...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/58C07C211/61C07C217/94C07C209/10C07C209/32C07C211/56C07C213/02C07C213/08C08G69/26C08G69/28C08G69/32C08G69/42C09K9/02
CPCC07C211/58C07C211/61C07C217/94C07C209/10C07C209/325C07C213/02C07C213/08C08G69/26C08G69/32C08G69/42C08G69/28C09K9/02C07C2603/24C09K2211/1433C09K2211/1416C07C211/56Y02P20/584
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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