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Fluorescent probe and application thereof to detection of explosives as well as preparation

A fluorescent probe and reaction technology, applied in the field of fluorescent probes, achieves the effects of convenient post-processing, low cost investment, and simple synthetic routes

Inactive Publication Date: 2017-06-23
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there is no synthesis method and application of quinone-based fluorescent probes based on the structure of 2-ethynylpyridine. Therefore, this patent describes the synthesis method of this type of fluorescent probe and its application in the detection of explosives such as nitro compounds. application in

Method used

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  • Fluorescent probe and application thereof to detection of explosives as well as preparation
  • Fluorescent probe and application thereof to detection of explosives as well as preparation
  • Fluorescent probe and application thereof to detection of explosives as well as preparation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The synthesis of embodiment 1 triptylenoquinone:

[0030] Add 0.41g (2.30mmol) of anthracene, 1.39g (12.86mmol) of p-benzoquinone and 40mL of acetic acid into a 100mL three-necked flask. Start the stirrer, heat to reflux for 6 hours, after the reaction is cooled to room temperature, filter with suction, wash the filter residue with hot water, and dry to obtain 0.37g (1.30mmol) triptylenoquinone with a yield of 56.6%. by mass spectrometry, 1 H-NMR and 12 The C-NMR spectrum confirmed that the product was triptylenoquinone.

Embodiment 2

[0031] The synthesis of embodiment 2 pentaphenylenone:

[0032] Add 0.18g (1.00mmol) anthracene, 0.28g (1.00mmol) triptylenone, 0.25g (1.00mmol) chloranil and 60mL acetic acid into a 100mL three-necked flask. Start the stirrer, heat to reflux for 36 hours, cool the reaction to room temperature, filter with suction, wash the filter residue with ether, and dry to obtain 0.26g (0.57mmol) pentadecenequinone with a yield of 56.5%. by mass spectrometry, 1 H-NMR and 12 The C-NMR nuclear magnetic spectrum confirms that the product is pentastylenoquinone.

Embodiment 3

[0033] Synthesis of Example 3 2-ethynylpyridinium (compound IV):

[0034] A 10 mL three-neck flask was placed in an ice-water bath and flushed with nitrogen, and 0.5 mL (4.56 mmol) of 2-ethynylpyridine and 5 mL of anhydrous and oxygen-free tetrahydrofuran were added. Start the stirrer and cool the reactant to 0°C, and add 1.9 mL of 2.7M n-butyllithium / n-hexane solution dropwise under stirring and nitrogen protection to obtain a solution containing compound IV. It was confirmed by mass spectrometry that the product contained compound IV.

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Abstract

The invention relates to a fluorescent probe with generation of quenching phenomenon of fluorescence intensity in the existence of nitro compounds and other explosives. The structure of the fluorescent probe is shown, wherein R1-R4 are H, alkyl, aryl or substituent containing hetero atoms. The fluorescent probe has a large cavity structure in order to effectively combine nitro compounds, the electron-rich structure of the probe and electron deficiency performance of the nitro compounds determine a partial coupling effect of the charges after the two parts are combined, and quenching of fluorescence is generated, so that the effects for detecting nitro compounds and other explosives are realized.

Description

technical field [0001] The invention relates to the field of fluorescent probes, in particular to a method for synthesizing the fluorescent probe and its application in detecting explosives such as nitro compounds. Background technique [0002] In recent years, terrorist activities have become increasingly rampant around the world, such as the 2004 Russian plane bombing, the 2006 Mumbai train bombing, the 2008 Jaipur bombing in India, and the 2010 Moscow subway bombing. Weapons are very easy to manufacture, but they can cause great damage and damage, especially in densely populated areas such as stations and airports. Therefore, the development of highly efficient and sensitive methods for detecting explosives such as nitro compounds has become a global safety issue and has been put on the agenda. [0003] At present, many methods for detecting explosives have been developed, such as chemical field test method, chemical resistance method, portable mass spectrometry, gas chr...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D213/127C07D213/06G01N21/64
CPCC09K11/06C07D213/06C07D213/127C09K2211/1029G01N21/643G01N2021/6432
Inventor 韩克利张学祥李鹏
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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