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Benzimidazole derivative and application thereof in detection of nitroaromatic explosives

A technology of benzimidazolylbenzene and benzimidazole, which is applied in the field of benzimidazole derivatives and its application in the detection of nitroaromatic explosives, and can solve the problem of rapid and simple visual detection of various aromatic explosives, etc. problems, to achieve the effect of simple and efficient preparation method, stable fluorescence emission, mild and safe conditions

Active Publication Date: 2021-12-17
SOUTH CHINA NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above-mentioned small-molecule fluorescent sensor can only detect picric acid alone in aqueous solution. In actual detection applications, there are often a variety of nitro-aromatic explosives in the polluted water source at the same time. They also pose a major threat to the environment, animals and plants. Such as picric acid, 2,4-dinitrophenol and p-nitrophenol
The above small molecule fluorescent sensors are not suitable for fast and simple visual detection of various aromatic explosives in actual polluted water samples. Therefore, it is necessary to develop a small molecule fluorescent sensor that can quickly and easily detect various aromatic explosives

Method used

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  • Benzimidazole derivative and application thereof in detection of nitroaromatic explosives
  • Benzimidazole derivative and application thereof in detection of nitroaromatic explosives
  • Benzimidazole derivative and application thereof in detection of nitroaromatic explosives

Examples

Experimental program
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Effect test

Embodiment 1

[0093] figure 1 Prepare the chemical reaction formula diagram of benzimidazole derivative compound 1 for embodiment 1, according to the following figure 1 , combined with the specific experimental steps of this example for further explanation.

[0094] Weigh 2mmol of 5-bromoisophthalic acid (a), 4.2mmol of o-phenylenediamine (b), place in a 50mL round bottom flask, add 15mL of polyphosphoric acid (PPA), raise the temperature to 170°C, and react 36h, after the reaction, the reaction solution was cooled to room temperature, then adjusted to pH 9-10 with NaOH solution, and suction filtered to obtain a solid crude product, then petroleum ether: ethyl acetate = 6:1 was selected as the eluent and passed through the column The pure intermediate 5-bromo-1,3-dibenzimidazolylbenzene (c) was obtained by chromatographic separation.

[0095] Weigh 0.5mmol intermediate 5-bromo-1,3-dibenzimidazolylbenzene (c), 0.6mmol 4-ethynyl-N,N-diphenylaniline (d), 0.05mmol cuprous iodide, 0.05mmol of...

Embodiment 2

[0097] figure 2 Prepare the chemical reaction formula diagram of benzimidazole derivative compound 2 for embodiment 2, according to the following figure 2 , combined with the specific experimental steps of this example for further explanation.

[0098] Weigh 2mmol of 5-bromoisophthalic acid (a), 4.2mmol of o-phenylenediamine (b), place in a 50mL round bottom flask, add 15mL of polyphosphoric acid (PPA), raise the temperature to 170°C, and react After 36 hours, after the reaction, the reaction liquid was cooled to room temperature, then adjusted to pH 9-10 with NaOH solution, and filtered with suction to obtain a solid crude product, and then petroleum ether and ethyl acetate were selected as eluents, separated by column chromatography The pure intermediate 5-bromo-1,3-dibenzimidazolylbenzene (c) was obtained.

[0099]Weigh 1mmol of compound intermediate 5-bromo-1,3-dibenzimidazolylbenzene (c), 4mmol of potassium hydroxide, measure 10mL of acetone, place in a 50mL round bot...

Embodiment 3

[0102] image 3 Prepare the chemical reaction formula diagram of benzimidazole derivative compound 3 for embodiment 3, according to the following image 3 , combined with the specific experimental steps of this example for further explanation.

[0103] Weigh 2mmol of 5-bromoisophthalic acid (a), 4.2mmol of 4,5-difluoro-o-phenylenediamine (f), place in a 50mL round bottom flask, add polyphosphoric acid (PPA) 15mL, and set the temperature Raise to 170°C and react for 36 hours. After the reaction, cool the reaction liquid to room temperature, then adjust the pH to 9-10 with NaOH solution, and filter with suction to obtain a solid crude product, and then use petroleum ether: ethyl acetate = 6:1 as The eluent was separated by column chromatography to obtain the pure intermediate g.

[0104] Weigh 0.5mmol compound intermediate g, 0.6mmol 4-ethynyl-N,N-diphenylaniline (d), 0.05mmol cuprous iodide, 0.05mmol dichlorobis(triphenylphosphine)palladium(II) , 3mL triethylamine, 3mL tetra...

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Abstract

The invention discloses a benzimidazole derivative and application of the benzimidazole derivative in detection of nitroaromatic explosives. The benzimidazole derivative provided by the invention is novel in structure and has an excellent fluorescence emission characteristic. The preparation method disclosed by the invention has the advantages of simplicity, high efficiency, cheap and easily available raw materials and mild and safe conditions. The benzimidazole derivative provided by the invention can be applied to rapid visual recognition of various nitroaromatic explosives in actual water samples, is an excellent fluorescent sensor, and can be further prepared into test paper and films for visual detection.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to a benzimidazole derivative and its application in detecting nitroaromatic explosives. Background technique [0002] In the existing technology, the methods or materials disclosed in the literature and patents for detecting aromatic explosives mainly include: surface-enhanced Raman spectroscopy, mass spectrometry, electrochemical methods, capillary electrophoresis, new explosive detectors and the use of Fluorescent sensor detection of metal complexes, metal organic frameworks (MOFs), organic polymers, covalent organic frameworks (COFs), etc. It is worth noting that the above-mentioned methods for detecting aromatic explosives are mainly divided into three types. One is the large-scale instrument detection method. Fluorescent sensors for substances and heavy metals, this type of method has a series of problems such as difficult to degrade, heavy metal pollution, and in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/18C07D403/14C09K11/06G01N21/64G01N21/78
CPCC07D235/18C07D403/14C09K11/06G01N21/6428G01N21/78C09K2211/1044C09K2211/1029G01N2021/6432
Inventor 汪朝阳陈思鸿
Owner SOUTH CHINA NORMAL UNIVERSITY
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