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Diamine compound containing three N centers, preparation method and application of diamine compound, polyamide, and preparation and application thereof

A technology of amine compound and polyamide, which is applied in the field of polyamide and its preparation and application, can solve the problems of high oxidation potential of single cation free radicals, instability of dications, unfavorable development and utilization of multi-color photoelectric materials, etc.

Active Publication Date: 2021-11-02
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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  • Diamine compound containing three N centers, preparation method and application of diamine compound, polyamide, and preparation and application thereof
  • Diamine compound containing three N centers, preparation method and application of diamine compound, polyamide, and preparation and application thereof
  • Diamine compound containing three N centers, preparation method and application of diamine compound, polyamide, and preparation and application thereof

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preparation example Construction

[0024] The present invention provides a preparation method of a diamine compound containing three N centers described in the above technical scheme, comprising the following steps:

[0025] Mix p-halogen nitrobenzene, N,N-dimethyl-p-phenylenediamine, a basic catalyst and a first polar solvent, and perform a first substitution reaction to obtain a diphenylamine derivative with a structure shown in formula II;

[0026] Mixing the diphenylamine derivative, the brominated fluorophore compound, the copper catalyst, the cocatalyst, the phase transfer catalyst and the second polar solvent, and performing a coupling reaction to obtain a mononitro compound with the structure shown in formula III;

[0027] Mixing the mononitro compound, the palladium carbon catalyst, hydrazine hydrate and the first mixed solvent, and performing the first reduction reaction to obtain the monoamino compound of the structure shown in formula IV;

[0028] Mixing the monoamino compound, p-halogen nitrobenzen...

Embodiment 1

[0086] Preparation of 4-N,N-dimethyl-4'nitrodiphenylamine:

[0087] Under nitrogen protection, add 27.2g (200mmol) N,N-dimethyl-p-phenylenediamine, 25.4g (180mmol) p-fluoronitrobenzene and 18.2g (180mmol) triethylamine into a 500mL three-necked flask, add 200mL DMSO, the solid content of the mixed system is 24.3wt%, reacted at 85°C for 20 hours, discharged in ice water, dried to obtain a dark red solid crude material, the crude material was mixed with ethanol and DMF with a volume ratio of 4:1 Liquid recrystallization, obtains purple crystal 42g, productive rate is 91%, structural formula is:

[0088]

[0089] Under nitrogen protection, 14.9g (58.0mmol) of the 4-N,N-dimethyl-4'nitrodiphenylamine, 10.0g (48.3mmol) of 2-bromonaphthalene, 46.0g (241.5mmol) of iodide Cuprous, 69.2g (193.2mmol) cesium carbonate and 12.2g (33.8mmol) dibenzo-18-crown-6 were added in a 500mL three-necked flask, and 227mL dichlorotoluene was added. The solid content of the mixed system was 35wt%. ...

Embodiment 2

[0098] 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 (168.5mmol) of copper powder, 18.6g (134.8mmol) of potassium carbonate and 5.3g (20.2mmol) of 18-crown-6 were added to a 250mL three-necked flask, and 75.0mL of dichlorotoluene was added to determine the solid content of the mixed system 36wt%, reacted at 175°C for 20h, filtered while hot to obtain the filtrate, distilled off the dichlorotoluene solution under reduced pressure, and carried out column layering of the solid crude material with a dichloromethane / petroleum ether developer with a volume ratio of 2.5:1 Analyze and purify, obtain 9.3g red mononitro compound 4-nitrophenyl-4-N, N dimethylphenyl-2-amino-2-bromo-6-methoxynaphthalene, productive rate is 56.0% , with the following structure:

[0099]

[0100] Under nitrogen protection, in a 250mL three-necked flask, 8.0g (19.3mmol) of the above-prepared ...

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Abstract

The invention provides a diamine compound containing three N centers, a preparation method and an application of the diamine compound, polyamide and preparation and an application of the polyamide, and belongs to the technical field of photoelectric materials. The diamine compound contains three N atom electroactive centers and a high-efficiency fluorophore R, the three N atoms can endow a polymer prepared from the diamine compound with multiple electrochromic behaviors, a double-p-phenylenediamine structure constructed by the diamine compound and a benzene ring can effectively stabilize cation free radicals, N, N-dimethyl is not only a third N atom center provider, but also can effectively reduce the oxidation potential of the polymer as a strong electron-donating group, so that the polymer has good electrochemical stability. Through the synergistic effect constructed by the efficient fluorophore and the propeller type triphenylamine, the polymer has high fluorescence contrast, and meanwhile, the stacking mode of the polymer is improved, so that the polymer has good solubility while maintaining the inherent thermal stability of the polymer.

Description

technical field [0001] The invention relates to the technical field of optoelectronic materials, in particular to a diamine compound containing a triple N center and its preparation method and application, polyamide and its preparation and application. Background technique [0002] Electroluminescence refers to the phenomenon that the fluorescence of materials undergoes reversible switching or discoloration under the action of an external electric field. Electrochromic materials refer to stable and reversible changes in their optical properties (absorption, transmission and reflection) under the action of an external electric field, and the macroscopic manifestations are changes in color and transparency. Fluorescent signals are generally detected in a dark background, and have the characteristics of low noise, high sensitivity, and low detection limit. Combining with electrochemistry, they have great development prospects in sensors, monitoring electrode surface reactions, ...

Claims

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Application Information

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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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