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Preparation and application of coumarin type fluorescent probe for detecting Hg<2+>

A fluorescent probe and coumarin-based technology, applied in the direction of fluorescence/phosphorescence, luminescent materials, measuring devices, etc., can solve the problems of complex operation process equipment, not suitable for in-situ analysis, etc., and achieve wide application prospects and good selectivity and the effect of sensitivity

Inactive Publication Date: 2019-12-10
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Common disadvantages of these techniques include the need for complex procedures or expensive equipment, and not being suitable for in situ analysis

Method used

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  • Preparation and application of coumarin type fluorescent probe for detecting Hg&lt;2+&gt;
  • Preparation and application of coumarin type fluorescent probe for detecting Hg&lt;2+&gt;
  • Preparation and application of coumarin type fluorescent probe for detecting Hg&lt;2+&gt;

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1: Preparation of 7-(diethylamino)-3-(1,3-dithian-2-yl)-2H-pyran-2-one

[0018]

[0019] Add 5mmol, 965mg of 4-diethylaminosalicylaldehyde into 20.0mL of ethanol to make it fully dissolved, then add 10mmol, 1.56mL of diethyl malonate and 5mmol, 494μL of piperidine, the amount of substance The ratio of 4-diethylaminosalicylaldehyde: diethyl malonate: piperidine=1:2:1, the reaction mixture was refluxed for 10h, monitored by TLC, the solvent was removed under reduced pressure, and then 10.0mL of concentrated hydrochloric acid and 10.0mL of glacial acetic acid was hydrolyzed, and stirred at 100°C for 6h, the solution was cooled to room temperature and poured into 50mL of ice water, 50% NaOH solution was added to adjust the pH to 7.0-8.0, then dichloromethane was added, and the organic layer was washed with water three times, Dry with anhydrous sodium sulfite, concentrate under reduced pressure, the crude product is purified by silica gel column chromatography, th...

Embodiment 2

[0022] figure 1 : Target compound detection Hg 2+ Mechanism research

Embodiment 3

[0024] figure 2 : In PBS buffer, the fluorescent molecular probe and Hg 2+ UV / Vis absorption spectrum after reaction

[0025] The emission spectrum of free DAC-Hg (10 μM) in PBS buffer (10 mM, 10% DMSO, pH 7.4) was collected 25 times. The excitation wavelength was 400nm, the voltage of the photomultiplier tube was set at 500V, and the slit width was set at 5.0nm, and the detection was performed on a Shimadzu UV-2550 instrument.

[0026] The results showed that the free probe DAC-Hg showed a peak at 403nm, while DAC-CHO and DACHg+Hg 2+ Both show a peak at 444nm. The fluorescence quantum yield of DAC-Hg determined subsequently was 0.93, and the detected product DAC-CHO was 0.27.

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Abstract

The invention relates to a preparation method and application of a coumarin type fluorescent probe; the compound is named as 7-(diethylamino)-3-(1,3-dithiane-2-yl)-2H-pyran-2-one. The compound has small molecular weight, simple structure and quite sensitive effect on Hg<2+>, shows excellent selectivity and sensitivity, is suitable for naked eye detection of Hg<2+>, has the detection limit of 5.0 nM which is the same as the most stringent Hg<2+> measurement standard, and has the potential of in-situ detection. The application of the established method in analysis of environment and seafood samples provides satisfactory results. Therefore, the compound provided by the invention provides a promising method for Hg<2+> detection and stimulates the development of induction of other heavy metal ions and transition metal ions. In a variety of water media, such as water, soil and seafood products, the probe further shows the potential of measuring and managing HTM ions, and has a broad application prospect.

Description

[0001] The invention relates to a method for preparing a fluorescent molecular probe of coumarin derivatives and its ability to detect Hg 2+ in the application. Background technique [0002] Heavy and transition metal (HTM) ions have received considerable attention in recent years because of their deleterious effects on the environment as well as living systems. Among these HTM ions, mercury is a well-known and highly toxic substance that can have harmful effects on human life and the environment even at very low concentrations. Releases of Hg from natural and industrial sources have been reported 2+ It is easy to enter the biofilm and accumulate in the human body through the food chain, thereby seriously damaging human health, such as Minamata disease, deafness and cognitive impairment. Current analytical methods for the detection of HTM ions include electrochemical techniques, inductively coupled plasma mass spectrometry, colorimetry, gas chromatography, and fluorescent pr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D409/04G01N21/64
CPCC09K11/06C07D409/04G01N21/643G01N2021/6432C09K2211/1088C09K2211/1092
Inventor 朱海亮苏咪咪徐云杰郑达俊杨冰徐琛
Owner NANJING UNIV
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