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Organic fluorescence sensing composite material with ultrahigh sensitivity response for explosives as well as preparation and application thereof

A technology of fluorescence sensing and composite materials, applied in the field of fluorescence sensing materials, can solve the problems of difficult detection and lack, and achieve the effect of improving detection limit and high fluorescence quantum efficiency

Active Publication Date: 2017-10-20
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In contrast, peroxides are difficult to detect due to their lack of nitro, no fluorescence and easy ionization ability, so how to realize online detection of peroxides and simultaneous detection of various nitro explosions It is a very challenging job

Method used

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  • Organic fluorescence sensing composite material with ultrahigh sensitivity response for explosives as well as preparation and application thereof
  • Organic fluorescence sensing composite material with ultrahigh sensitivity response for explosives as well as preparation and application thereof
  • Organic fluorescence sensing composite material with ultrahigh sensitivity response for explosives as well as preparation and application thereof

Examples

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preparation example Construction

[0084] As an example, the present invention provides the preparation method of the carbazole derivative when n=3 in the compound shown in (I), and described step (1') specifically comprises:

[0085] In a preferred embodiment of the present invention, the carbazole derivative of n=3 in the preparation formula (I), described step (1 ') specifically comprises:

[0086] (1a). Compound shown in formula (IIa) reacts with RX' to prepare compound shown in formula (IIIa)

[0087]

[0088] X in formula (IIa) and formula (IIIa) is the same or different, and is independently selected from halogen (such as Br, I); X' in RX' is selected from halogen (such as Br, I); Formula (IIIa) and The definition of R in RX' is the same as formula (I);

[0089] (1b). Compound shown in formula (IIIa) and R'B (OH) 2 Reaction makes the compound shown in formula (IV ')

[0090]

[0091] Formula (IV') and R'B(OH) 2 Among them, the definition of R' is the same as formula (I); In formula (IV'), the d...

Embodiment 1

[0138] Prepare compound 1 (in the formula (I), R is a linear octyl group, R' is 4-methoxyacylphenyl, n is 3) with the following structure, and its preparation method is as follows:

[0139]

[0140] (1) Dissolve 1 g of 2,7-dibromocarbazole in 30 ml of N,N-dimethylformamide (DMF) solution, place the above solution in an ice bath at 0°C, and slowly add 1.2 equivalents of 74mg of sodium hydride solid, after continuous stirring for half an hour, 1.5 equivalents of 1-bromooctane was slowly added, and after reacting at room temperature overnight, the product was obtained by column chromatography.

[0141] (2) Get 500 mg of the product obtained in step (1), add 20 ml of 1,4-dioxane solution, add 5 equivalents of bisvaleryl diboron, 14 equivalents of potassium acetate, 10% equivalents of [1,1 '-bis(diphenylphosphino)ferrocene]palladium dichloride was reacted for 6 hours at 80°C under the protection of argon, and the product (TM-1) was obtained by column chromatography.

[0142] (3...

Embodiment 2

[0145] Weigh 150 mg of compound 1 obtained in Example 1 and dissolve it in 10 ml of tetrahydrofuran (THF) solution, add 3-5 equivalents of KOH solid, add 5 ml of water, heat to 65 ° C and react overnight, add 1M HCl aqueous solution to adjust the pH To 2-3, at this time, a light yellow solid precipitated out, and the product was taken out and dried.

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Abstract

The invention relates to an organic fluorescence sensing composite material with ultrahigh sensitivity response for explosives as well as preparation and application thereof. The material is a blended one-dimensional organic semiconductor nanowire obtained by compositing one or more metallorganics complexes based on carbazole molecules and an organic fluorescence sensing material based on a series of carbazole molecules by a self-assembly method; the material has the characteristics of being porous, being large in superficial area, high in fluorescence quantum efficiency, uniform in mixing and the like, is suitable for fluorescence detection for the explosives and is particularly very efficient in detection for trace explosives.

Description

technical field [0001] The present invention relates to metal-organic complexes and organic composite fluorescent sensing materials, in particular to organic fluorescent sensing composite materials based on carbazole molecule-based metal-organic complexes and carbazole derivatives, and their preparation and detection of explosives. detection application. Background technique [0002] All kinds of explosives pose a great threat to social security, ecological environment and human health. Explosive detection research and detection technology are of great significance to environmental protection, anti-terrorism and social security. Explosives mainly include six categories, nitroalkanes (such as nitromethane, 2,3-dinitro-2,3-dimethylbutane (DMNB), etc.), nitroaromatic compounds (such as trinitrogen nitrotoluene (TNT), dinitrotoluene (DNT)), nitroamines (such as RDX), nitroesters (such as pentaerythritol tetranitroester (PETN)), black powder and peroxides class (such as hydrog...

Claims

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Application Information

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IPC IPC(8): C07D209/86C09K11/06G01N21/64
CPCC07D209/86C09K11/06C09K2211/1007C09K2211/1029C09K2211/187G01N21/643G01N2021/6432
Inventor 车延科熊伟朱其建
Owner INST OF CHEM CHINESE ACAD OF SCI
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