Fluorescent probe capable of detecting nerve poison in ratio multi-time visualization manner as well as preparation and application

A technology for fluorescent probes and nerve agents, which is applied in fluorescence/phosphorescence, organic chemistry, luminescent materials, etc., can solve the problems of difficult sensing materials, cumbersome synthesis and complex structure of organophosphorus nerve agent simulants, and achieves instrument interference The effect of small size, simple synthesis route and simple preparation process

Active Publication Date: 2020-09-01
HUNAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, the research work of using colorimetric and fluorescent methods to detect nerve agent simulants has been reported in some literatures (Sensors and Actuators B: Chemical 2019, 298, 126923; Journal of Materials Chemistry C 2016, 4, 10105-10110; ACS Macro Lett, 2015, 4, 138—142), but most of these probes are either limited to detection in solution, or can no longer be used after one use, and a few materials that can realize two-phase detection usually have complex structures and cumbersome synthesis
Therefore, it is still difficult to design simple and efficient sensing materials for organophosphorus nerve agent simulants that can be used for both solution and gas phase detection and are reusable.

Method used

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  • Fluorescent probe capable of detecting nerve poison in ratio multi-time visualization manner as well as preparation and application
  • Fluorescent probe capable of detecting nerve poison in ratio multi-time visualization manner as well as preparation and application
  • Fluorescent probe capable of detecting nerve poison in ratio multi-time visualization manner as well as preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] (1) 1386mg 7-diethylamino-4-methylcoumarin (6mmol) was dissolved in 20mL tetrahydrofuran and precooled at 0°C for half an hour, and 1280mg N-bromosuccinimide (7.2mmol) was slowly added, React overnight at room temperature, pour 20mL of concentrated brine after the end of the reaction, extract three times with 20mL of dichloromethane, dry the organic phase with anhydrous sodium sulfate, filter; rotary evaporation removes the organic solvent, and the resulting solid is purified by silica gel column chromatography ( The eluent was petroleum ether / dichloromethane, V / V=3:2), and 1760 mg of 3-bromo-7-diethylamino-4-methylcoumarin was obtained as a light yellow solid (94.6% yield). The product was characterized by H NMR spectroscopy, as figure 2 Shown, 1H NMR (500MHz, CDCl3) δ7.37 (d, J = 9.1Hz, 1H), 6.57 (dd, J = 9.1, 2.5Hz, 1H), 6.41 (t, J = 7.1Hz, 1H), 3.38 (q, J = 7.1 Hz, 4H), 2.47 (s, 3H), 1.18 (t, J = 7.1 Hz, 6H). Among them, 6.41ppm is the single peak on the benzene ...

Embodiment 2

[0039] (1) 1386mg 7-diethylamino-4-methylcoumarin (6mmol) was dissolved in 20mL tetrahydrofuran and precooled at 0°C for half an hour, and 1315mg N-bromosuccinimide (7.4mmol) was slowly added, React overnight at room temperature, pour 20mL of concentrated brine after the end of the reaction, extract three times with 20mL of dichloromethane, dry the organic phase with anhydrous sodium sulfate, filter; rotary evaporation removes the organic solvent, and the resulting solid is purified by silica gel column chromatography ( The eluent was petroleum ether / dichloromethane, V / V=3:2), and 1770 mg of 3-bromo-7-diethylamino-4-methylcoumarin was obtained as a light yellow solid (95.2% yield).

[0040] (2) 154mg 3-bromo-7-diethylamino-4-methylcoumarin (0.5mmol), 4.5mg palladium acetate (0.02mmol), 15.7mg triphenylphosphine (0.06mmol), 63mg 4-ethylene Pyridine (0.6mmol) and 15mL triethylamine were added to the Schlenk tube one by one in order, and the air in the tube was immediately sucked...

Embodiment 3

[0042] (1) 1386mg 7-diethylamino-4-methylcoumarin (6mmol) was dissolved in 20mL tetrahydrofuran and precooled at 0°C for half an hour, and 1246mg N-bromosuccinimide (7.0mmol) was slowly added, React overnight at room temperature, pour 20mL of concentrated brine after the end of the reaction, extract three times with 20mL of dichloromethane, dry the organic phase with anhydrous sodium sulfate, filter; rotary evaporation removes the organic solvent, and the resulting solid is purified by silica gel column chromatography ( The eluent was petroleum ether / dichloromethane, V / V=3:2), and 1680 mg of 3-bromo-7-diethylamino-4-methylcoumarin was obtained as a light yellow solid (90.3% yield).

[0043] (2) 154mg 3-bromo-7-diethylamino-4-methylcoumarin (0.5mmol), 4.5mg palladium acetate (0.02mmol), 15.7mg triphenylphosphine (0.06mmol), 84mg 4-ethylene Pyridine (0.8mmol) and 15mL triethylamine were added to the Schlenk tube one by one in order, and the air in the tube was immediately sucked...

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Abstract

The invention discloses a fluorescent probe capable of detecting a nerve poison in a ratio mult-time visualization manner as well as preparation and application. The probe is a ratio type fluorescentprobe prepared from 7-diethylamino-4-methylcoumarin, N-bromosuccinimide and p-nitrobenzyl bromide as raw materials. The probe can realize high-sensitivity ratio fluorescence detection on diethyl chlorophosphate. Compared with an existing fluorescence detection technology, the obtained fluorescence probe has double-ratio detection and repeated use functions, is high in fluorescence, simple in synthetic route, simple and convenient in detection method and suitable for amplification synthesis and actual production application, and has huge application prospects in the technical fields of analytical chemistry, life science, environmental science and the like.

Description

technical field [0001] The invention belongs to the field of chemical material preparation and analysis and detection, and relates to the preparation and application of a fluorescent probe capable of ratiometrically detecting nerve agents, in particular, to a fluorescent probe capable of ratiometrically detecting nerve agents and its preparation and application . Background technique [0002] Since the 21st century, terrorist incidents have occurred frequently in the world, and organophosphorus nerve agents such as sarin, tabun, and soman are often used by terrorists as chemical weapons, so the detection of organophosphorus nerve agents is receiving more and more scientific research workers' attention. The characteristic of this type of nerve agent is that it can damage the body through skin, eye contact or inhalation through the respiratory tract, leading to dysfunction of the central nervous system, and even fatal in severe cases. Moreover, most of these poisons are colo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/06C09K11/06G01N21/64
CPCC07D405/06C09K11/06G01N21/643C09K2211/1029C09K2211/1088
Inventor 张培盛任俊宇刘会田勇李静雯陈建张崇华
Owner HUNAN UNIV OF SCI & TECH
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