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Fluorescent sensing material, preparation method thereof and application thereof in high-sensitivity detection of explosives

A technology for fluorescent materials and explosives, applied in the field of organic fluorescent sensing materials, can solve problems such as easy photooxidation, low luminous efficiency, and poor photostability

Active Publication Date: 2020-06-26
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, among the currently reported explosive detection materials based on the fluorescence detection method, many materials have the disadvantages of easy photooxidation, poor photostability and low luminous efficiency, which are difficult to be applied in actual measurement.
Therefore, it is a huge challenge for developers to ensure the sensitive detection of explosives while improving the photostability and luminous efficiency of the material.

Method used

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  • Fluorescent sensing material, preparation method thereof and application thereof in high-sensitivity detection of explosives
  • Fluorescent sensing material, preparation method thereof and application thereof in high-sensitivity detection of explosives
  • Fluorescent sensing material, preparation method thereof and application thereof in high-sensitivity detection of explosives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0108] Preparation of compound A, the preparation method is as follows:

[0109]

[0110] (1) Add 3 g of 4-bromoanisole, 4.5 g of bis-valeryl diboron, 4.9 g of potassium acetate, and 0.5 g of 1,1'-bis(diphenylphosphino)ferrocene into a 100 mL round bottom flask Palladium(II) dichloride was added with 20 ml of anhydrous 1,4-dioxane, argon gas was introduced to exhaust oxygen, and the reaction was carried out at 80 degrees Celsius for 8 hours, and the obtained product was obtained after separation by column chromatography.

[0111] (2) Take 2 grams of the product obtained in step (1), add 20 mL of 1,4-dioxane and 4 mL of water into the mixture, and add 4 grams of 9,9-dihexyl-2,7-dibromofluorene , 3.3 grams of potassium carbonate, 0.5 grams of tetrakis (triphenylphosphine) palladium, passed through argon to exhaust oxygen, and reacted for 8 hours at 80 degrees Celsius, and the resulting product was obtained after separation by column chromatography.

[0112] (3) Add 2 grams o...

Embodiment 2

[0121] Preparation of compound B, the preparation method is as follows:

[0122]

[0123] (1) Add 2 grams of 4-bromophenol, 1 gram of 2-butanol, 30 milliliters of tetrahydrofuran, and 3 grams of triphenylphosphine into a round-bottomed flask, pass through argon to exhaust oxygen, and then slowly add 2.8 1 g of diisopropyl azodicarboxylate, returned to normal temperature after the dropwise addition, stirred for 5 hours, and obtained product was obtained after separation by column chromatography.

[0124] (2) Add 1.5 grams of the product obtained in step (1) to a 100mL round bottom flask, add 2 grams of bisvaleryl diboron, 2 grams of potassium acetate and 0.3 grams of 1,1'-bis(diphenylphosphino) ) Ferrocene palladium dichloride (II) was added with 30 milliliters of anhydrous 1,4-dioxane, argon was passed through to exhaust oxygen, and reacted at 80 degrees Celsius for 8 hours, and the obtained product was obtained after separation by column chromatography.

[0125] (3) Add 1...

Embodiment 3

[0137] Compound A in Example 1 and Compound B in Example 2 are dissolved in a good solvent, and then a poor solvent is added, the good solvent is chloroform, the poor solvent is methanol, and the volume ratio of the good solvent to the poor solvent is 1: 15. After standing still, a suspension of organic semiconductor microspheres with different fluorescent responses to several types of explosives was obtained by self-assembly. SEM images such as Figure 11 shown. Such as Figure 12 As shown, the fluorescence intensity of the fluorescent sensing material self-assembled by Compound A decreased by 70% after 4 hours of continuous illumination, while the fluorescence intensity of the organic fluorescent sensing material co-assembled by the two molecules only decreased after 4 hours of continuous illumination. 12%, indicating that after adding benzothiadiazole derivatives for co-assembly, the photostability is greatly improved. Another small amount of aggregates was placed in an ...

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Abstract

The invention relates to an organic fluorescent sensing material, which is formed by co-assembling a fluorene derivative represented by a formula (I) and a benzothiadiazole derivative represented by aformula (II). The organic fluorescent sensing material can overcome the problems of poor stability and low luminous efficiency when the compound of the formula (I) is singly used and poor detection effect when the compound of the formula (II) is singly used. Advantages of different molecules are effectively integrated by adopting co-assembly, and the material obtained by co-assembling antioxidantmolecules (compounds shown in the formula (II)) and molecules (compounds shown in the formula (I)) with excellent detection performance can well solve the problems of poor stability and low luminousefficiency of the material. The detection limit of the fluorescent material disclosed by the invention reaches ng level, and the fluorescent material has no obvious response to common interfering gases such as organic solvents (thousands to tens of thousands ppm), so that the detection method disclosed by the invention has very strong practicability to the detection of explosives.

Description

technical field [0001] The invention belongs to the field of organic fluorescent sensing materials, and in particular relates to a fluorescent sensing material, a preparation method thereof and an application in high-sensitivity detection of explosives. Background technique [0002] In the national security and anti-terrorist struggle, bomb explosion is by far the most common form of terrorism. Because explosives are easy to manufacture and deploy, they are likely to cause tens of thousands of casualties and cause huge property losses. Therefore, explosives Detection is an urgent problem to be solved. If sensitive detection of these explosives can be realized, it will be of great significance to national security and protection of people's property. Common explosives are mainly divided into the following categories: nitroalkanes (such as NM, etc.), nitroaromatic compounds (such as DNT, TNT, etc.), nitroamines (such as RDX, etc.), nitroesters (such as PETN, etc.), black pow...

Claims

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Application Information

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IPC IPC(8): C09K11/06G01N21/64C07D285/14
CPCC07D285/14C09K11/06C09K2211/1007C09K2211/1011C09K2211/1051G01N21/643
Inventor 车延科程传钦
Owner INST OF CHEM CHINESE ACAD OF SCI
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