Benzimidazolyl chemical sensor used for fluorescence quenching detection of nitroaromatic explosives, and preparation method of benzimidazolyl chemical sensor

A benzimidazole-based, chemical sensor technology, applied in the field of detection of nitroaromatic explosives, can solve the problems of few types and difficult preparation of chemical sensors, and achieve the effects of easy temperature control, easy product, and rapid synthesis

Inactive Publication Date: 2016-10-12
SOUTH CHINA NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0007] The object of the present invention is to provide a method for nitroaromatics in view of defects such as the high sensitivity and high selectivity of solid-state detection of NAC based on organic small molecule fluorescence, especially the chemical sensor of PA, which is difficult to prepare and has fewer types. A novel bis(benzimidazole)naphthalene fluorescent chemical sensor for the detection of similar explosives and a preparation method thereof, the preparation method is simple, the structure of the target compound is varied, the effect is obvious, and it has a good industrial application prospect

Method used

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  • Benzimidazolyl chemical sensor used for fluorescence quenching detection of nitroaromatic explosives, and preparation method of benzimidazolyl chemical sensor
  • Benzimidazolyl chemical sensor used for fluorescence quenching detection of nitroaromatic explosives, and preparation method of benzimidazolyl chemical sensor
  • Benzimidazolyl chemical sensor used for fluorescence quenching detection of nitroaromatic explosives, and preparation method of benzimidazolyl chemical sensor

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Experimental program
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Effect test

Embodiment 1

[0041] (1) With 0.523 grams of 1-bromododecane and 0.389 grams of 2,6-two (5-methylbenzimidazole) naphthalene (that is, in the structural formula of the aforementioned two (benzimidazole) naphthalene compounds, the benzimidazole group is located at The 2,6-position of the naphthalene ring, and R 1 =CH 3) as a raw material, according to the amount of substance ratio n (1-bromododecane):n (2,6-bis (5-methylbenzimidazole) naphthalene) = 2.1:1 mixed evenly, at a temperature of 80 ° C, 0.160 gram of NaOH solid is catalyst and 10 milliliters of acetonitrile is under the condition of solvent, carries out N-alkylation substitution reaction 2 hours;

[0042] (2) After the reaction is over, dissolve and transfer with ethyl acetate, wash the organic phase 3 times, take the organic phase, dry over anhydrous magnesium sulfate, spin off the solvent, and the crude product is separated by column chromatography to obtain the white solid bis(benzimidazole ) Naphthalene-based novel fluorescent...

Embodiment 2

[0049] (1) With 0.523 grams of 1-bromododecane and 0.389 grams of 2,6-two (5-methylbenzimidazole) naphthalene (that is, in the structural formula of the aforementioned two (benzimidazole) naphthalene compounds, the benzimidazole group is located at The 2,6-position of the naphthalene ring, and R 1 =CH 3 ) as a raw material, according to the amount of substance ratio n (1-bromododecane):n (2,6-bis (5-methylbenzimidazole) naphthalene) = 2.1:1 mixed evenly, at a temperature of 80 ° C, 0.080 gram of NaOH solid is catalyst and 10 milliliters of acetonitrile is under the condition of solvent, carries out N-alkylation substitution reaction 10 hours;

[0050] (2) After the reaction is over, dissolve and transfer with ethyl acetate, wash the organic phase 3 times, take the organic phase, dry over anhydrous magnesium sulfate, spin off the solvent, and the crude product is separated by column chromatography to obtain the white solid bis(benzimidazole ) Naphthalene-based novel fluoresce...

Embodiment 3

[0054] (1) With 1.247 grams of 1-bromododecane and 0.389 grams of 2,6-two (5-methylbenzimidazole) naphthalene (that is, in the structural formula of the aforementioned two (benzimidazole) naphthalene compounds, the benzimidazole group is located at The 2,6-position of the naphthalene ring, and R 1 =CH 3 ) as a raw material, according to the amount of substance ratio n (1-bromododecane):n (2,6-bis (5-methylbenzimidazole) naphthalene) = 5:1 mixed evenly, at a temperature of 80 ° C, 0.160 gram of NaOH solid is catalyst and 10 milliliters of acetonitrile is under the condition of solvent, carries out N-alkylation substitution reaction 2 hours;

[0055] (2) After the reaction is over, dissolve and transfer with ethyl acetate, wash the organic phase 3 times, take the organic phase, dry over anhydrous magnesium sulfate, spin off the solvent, and the crude product is separated by column chromatography to obtain the white solid bis(benzimidazole ) Naphthalene-based novel fluorescent ...

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Abstract

The invention relates to a benzimidazole-based chemical sensor for fluorescence quenching detection of nitroaromatic explosives and a preparation method thereof. Using bis(benzimidazole)naphthalene and halogenated hydrocarbons as raw materials, mainly through simple and easy N ‑Alkylation substitution reaction to prepare a benzimidazole-based fluorescent chemical sensor with high selectivity and high sensitivity to detect explosive NAC, which mainly detects PA. The prepared benzimidazole-based fluorescent chemical sensor can visually detect PA in solution and in solid state by using fluorescence quenching under ultraviolet light, and can realize the detection of gaseous PA. The present invention proposes for the first time the structure and synthesis method of a novel bis(benzimidazole)naphthalene chemical sensor based on fluorescence quenching detection of nitroaromatic compounds. The sensor provides highly selective and sensitive detection of explosive nitroaromatic compounds, especially picric acid, in multiple ways.

Description

technical field [0001] The invention belongs to the technical field of detection of nitroaromatic explosives, in particular to a benzimidazole-based chemical sensor for fluorescence quenching detection of nitroaromatic explosives and a preparation method thereof. Background technique [0002] Because explosive nitroaromatic compounds (NAC) have caused many adverse effects on safety, environment and health, especially the sharp increase in demand for anti-terrorism, non-metal mine detection, and environmental quality monitoring, the micro-trace detection of NAC has attracted attention. There is an urgent need to develop low-cost, high-efficiency, easy-to-use, selective, rapid and sensitive detection methods. Among them, high-sensitivity and high-selectivity fluorescence detection methods have attracted much attention in recent years. However, few reports have been reported on chemical sensors for the solid-state detection of NAC, especially picric acid (PA), based on organic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/18C09K11/06G01N21/64
CPCC07D235/18C09K11/06C09K2211/1044G01N21/6428G01N2021/6432
Inventor 汪朝阳吴彦城
Owner SOUTH CHINA NORMAL UNIVERSITY
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