Organic fluorescent sensing material with high-sensitivity fluorescent response to several explosives, and preparation method application of organic fluorescent sensing material

A fluorescence sensing and fluorescence response technology, applied in luminescent materials, fluorescence/phosphorescence, organic chemistry, etc., can solve the problems of unfavorable detection, single detection object, low sensitivity, etc., and achieve high selectivity, high sensitivity, and high stability. sexual effect

Active Publication Date: 2017-01-04
INST OF CHEM CHINESE ACAD OF SCI
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Problems solved by technology

[0004] The currently reported explosives detection materials based on the fluorescence detection method have defects s

Method used

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  • Organic fluorescent sensing material with high-sensitivity fluorescent response to several explosives, and preparation method application of organic fluorescent sensing material
  • Organic fluorescent sensing material with high-sensitivity fluorescent response to several explosives, and preparation method application of organic fluorescent sensing material
  • Organic fluorescent sensing material with high-sensitivity fluorescent response to several explosives, and preparation method application of organic fluorescent sensing material

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preparation example Construction

[0077] As mentioned above, the present invention discloses a method for preparing an organic fluorescent sensing material with fluorescent response to several types of explosives. The method comprises the following steps: (1) firstly synthesizing the carbazole derivative, (2) Then, in the mixture of good solvent and poor solvent, the organic fluorescent sensing material is obtained by self-assembly.

[0078] In a preferred embodiment of the present invention, the carbazole derivative of n=3 in the preparation formula (I), said step (1) specifically comprises:

[0079] (1a) the compound shown in the formula (II) reacts with RX ' to prepare the compound shown in the formula (III);

[0080]

[0081] X in formula (II) and formula (III) 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 (III) and The definition of R in RX' is the same as formula (I);

[0082] (1b) compound shown in f...

Embodiment 1

[0127] Preparation has the following molecular 1 R is a straight-chain octyl group, R' is a 4-methoxyacylphenyl group, and n is a carbazole derivative of 3, and its preparation method is as follows:

[0128]

[0129] (1) Dissolve 1 g of 2,7-dibromocarbazole in 30 ml of N,N-dimethyl-formamide (DMF) solution, place the above solution in an ice bath at 0°C, and slowly add 1.2 The equivalent of 74 mg of sodium hydride solid was continuously stirred for half an hour, then 1.5 equivalent of 1-bromooctane was slowly added, and after reacting overnight at room temperature, the product was obtained by column chromatography.

[0130] (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 chr...

Embodiment 2

[0135] Preparation has the following molecule 2 R is an isobutyl group, R' is a 4-methoxyacylphenyl group, and n is a carbazole derivative of 3, and its preparation method is as follows:

[0136]

[0137] (1) Add 14.2g p-toluenesulfonyl chloride (TsCl) to 150ml dichloromethane, add 824mg DMAP and 15g triethylamine under argon protection and 0°C ice bath, after deoxygenation, add 5g iso Butanol was dissolved in 50ml of dichloromethane, slowly added to the above solution, after the reaction was stirred overnight, a saturated sodium bicarbonate solution was added to quench the reaction, after extraction with 100ml×3 dichloromethane, the organic phases were combined, and anhydrous sulfuric acid was added After sodium drying, the product was spin-dried.

[0138] (2) Dissolve 1 gram of 2,7-dibromocarbazole in 30 ml of DMSO, slowly add 9 equivalents of 1.55 g of potassium hydroxide solid, continue stirring for half an hour, slowly add 1.5 equivalents of 1.05 g of the step The produ...

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Abstract

The invention relates to an organic fluorescent sensing material with high-sensitivity fluorescent response to several explosives, and a preparation method application of the organic fluorescent sensing material. The material is obtained by self-assembling one or various carbazole derivatives through pi-pi interaction. The organic fluorescent sensing material disclosed by the invention has a typical P type material characteristic and high luminous stability, is suitable for being used for performing fluorescence detection on the explosives, and is particularly very effective for the detection of trace explosives (the concentration is at the ng level).

Description

technical field [0001] The invention belongs to organic fluorescent sensing materials, in particular to the design and synthesis of a P-type semiconductor based on carbazole molecules and its application to the fluorescent detection of several types of explosives. Background technique [0002] The detection of explosives is of great significance to the ecological environment, national security, military and other fields. At present, the detection of explosives mainly focuses on trinitrotoluene (TNT) and dinitrotoluene (DNT), and there are very few reports on other types such as TATP, RDX, PETN and S. Many explosive detection methods have been reported in the literature, and the main techniques for the detection of a large number of explosives are: X-ray diffraction, neutron analysis, electron capture, surface acoustic wave and other methods. This type of method has been applied in practice. Although the technology is relatively mature, it cannot meet the practical applicati...

Claims

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Application Information

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IPC IPC(8): C07D209/86C09K11/06G01N21/64
Inventor 车延科熊伟
Owner INST OF CHEM CHINESE ACAD OF SCI
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