Nitrogen-containing heterocyclic compound, organic fluorescent film, preparation method and application

A nitrogen heterocyclic compound and organic technology, applied in the field of fluorescence detection, can solve the problem of low sensitivity and the like, and achieve the effects of solving the problem of low sensitivity, broad application prospect and simple preparation method

Active Publication Date: 2020-10-02
NORTHEAST FORESTRY UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a nitrogen-containing heterocyclic compound to solve the problem of low sensitivity of the existing fluorescent materials used for nerve gas detection proposed in the above-mentioned background technology

Method used

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  • Nitrogen-containing heterocyclic compound, organic fluorescent film, preparation method and application
  • Nitrogen-containing heterocyclic compound, organic fluorescent film, preparation method and application
  • Nitrogen-containing heterocyclic compound, organic fluorescent film, preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0053] A preparation method of a nitrogen-containing heterocyclic compound, the nitrogen-containing heterocyclic compound is specifically 3cp, and the corresponding synthetic route is as follows:

[0054]

[0055] In this embodiment, the specific preparation method includes the following steps:

[0056] 1) Synthesis of N-phenyl-9-(4,4,5,5-tetramethyl-1,3,2-dioxolane)carbazole: Weigh 1.00g of 9-(4- Bromophenyl) carbazole, 1.57g of pinacol diborate and 1.82g of potassium acetate were dissolved in 30mL of 1,4-dioxane, and under the protection of nitrogen, they were fed into liquid nitrogen and frozen for 8 minutes. Then vacuumize for 5 minutes, add 150 mg of catalyst (1,1-bis(diphenylphosphino)ferrocene)palladium dichloride, freeze and vacuumize three times, remove oxygen, reflux at 85°C for 24 hours, and then react The product was transferred to a separatory funnel, extracted, and a mixed solvent of dichloromethane and petroleum ether was used as an eluent, and column chroma...

Embodiment 2

[0060] A preparation method of a nitrogen-containing heterocyclic compound, the nitrogen-containing heterocyclic compound is specifically 3c, and the corresponding synthetic route is as follows:

[0061]

[0062] In this embodiment, the specific preparation method includes the following steps:

[0063] Carbazole (3mmol) and 3,6,11-tribromo-dibenzophenazine (1mmol) were added to a 250mL round bottom flask, then cuprous iodide (0.6mmol), potassium phosphate (18mmol) and 1,2-cyclohexanediamine (16mmol) was added to the aforementioned 250mL round bottom flask, then 100mL of toluene was added, frozen to a solid state by liquid nitrogen, pumped for 5 minutes, and the catalyst Pd(PPh 3 ) 4 (60mg), sealed; refreezing, pumping, and thawing were repeated twice, and refluxed at 110°C for 36 hours under the protection of nitrogen; Dry over sodium sulfate and spin dry, the crude product is purified by column chromatography with dichloromethane / petroleum ether (the volume ratio of dich...

Embodiment 3

[0065] The nitrogen-containing heterocyclic compound (3cp) prepared in Example 1 was added into dichloromethane to prepare a solution with a concentration of 0.1 mg / mL (solvent is dichloromethane), and then prepared by electropolymerization to obtain an organic fluorescent film, denoted as 3cp-EP; wherein, in the electropolymerization method, the electrolyte is tetrabutylammonium hexafluorophosphate of 38.7mg / mL, with ITO (Indium tin oxide, indium tin oxide) glass as the working electrode, and the Ag / Ag+ electrode as the reference Specific electrode, with titanium plate as auxiliary electrode, electropolymerization start voltage 0V, end voltage 0V, low potential voltage 0V, high potential voltage 1.1V, scanning rate 0.2V / s, scanning circles 50 circles, sensitivity 10 -4 mA. After electropolymerization, the organic fluorescent film was washed with dichloromethane / acetonitrile (the volume ratio of dichloromethane:acetonitrile is 4:1), and vacuum-dried at 45° C. for 1 hour.

[0...

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Abstract

The invention relates to the technical field of fluorescence detection and particularly discloses a nitrogen-containing heterocyclic compound, an organic fluorescent film, a preparation method and application. The nitrogen-containing heterocyclic compound belongs to an organic conjugated nitrogen heterocyclic ring molecule, the central nucleus of the molecule has an electron-deficient nitrogen heterocyclic ring structure, and high-sensitivity detection of a nerve poison and/or a nerve poison simulant is realized through lone pair electrons on nitrogen. The preparation method of the nitrogen-containing heterocyclic compound provided by the invention is simple; according to the invention, the nitrogen-containing heterocyclic compound is made into the organic fluorescent film through the electropolymerization method; the method has the advantages of low detection cost, environmental protection, simple operation, high sensitivity, short detection time, repeated use and the like, the problem of low sensitivity of the existing fluorescent material for nerve poison gas detection is solved, and the method has a wide application prospect.

Description

technical field [0001] The invention relates to the technical field of fluorescence detection, in particular to a nitrogen-containing heterocyclic compound, an organic fluorescent film, a preparation method and an application. Background technique [0002] With the continuous development of society, the importance of public safety is also increasing. In order to alleviate the serious threats to public safety caused by sudden terrorist attacks and industrial accidents, it is very important to quickly and accurately analyze highly toxic nerve gases (nerve agents) and their related chemicals. At present, the development and research of nerve gas detection methods have been receiving much attention, and the detection of nerve agents such as tabun, sarin, soman and Viex needs to be able to achieve high selectivity and convenience of detection, usually using Diethyl chlorophosphate (DCP, Diethyl chlorophosphate) was used as a nerve agent simulant to study nerve gas detection meth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/14C08G61/12C09K11/06G01N21/64C25D9/02
CPCC07D403/14C08G61/124C08G61/122C09K11/06G01N21/643C25D9/02C09K2211/1466C08G2261/11C08G2261/44C08G2261/522C08G2261/3241C08G2261/312C08G2261/18Y02E10/549
Inventor 马洪伟莫万齐李晓白
Owner NORTHEAST FORESTRY UNIVERSITY
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