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Ratio type probe for detecting mercury ions and preparation method and application thereof

A mercury ion, ratio-type technology, applied in chemical instruments and methods, measuring devices, and analysis through chemical reactions of materials, can solve problems such as long synthesis routes and unsatisfactory detection

Active Publication Date: 2021-06-22
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the reported probes for the detection of mercury ions show good sensitivity and selectivity to mercury ions, but these probes also have disadvantages such as long synthetic routes and unsatisfactory detection.

Method used

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  • Ratio type probe for detecting mercury ions and preparation method and application thereof
  • Ratio type probe for detecting mercury ions and preparation method and application thereof
  • Ratio type probe for detecting mercury ions and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1 Weigh 2.44g (10mmol ) 7-diethylamino-2-oxo-1,2-dihydroquinoline-3-carbaldehyde in a 100mL two-necked bottle, add 2.60g (10mmol) 3-acetyl-7-diethylaminocoumarin, 50mL Ethanol was stirred to dissolve, then 1.0 mL of acetic acid and 1.0 mL of piperidine were added, the solution was dark reddish brown, heated to 75°C, and the reaction progress was detected by TLC. After the reaction was complete, cool to room temperature, a red solid was precipitated, filtered under reduced pressure, and washed with methanol to obtain 4.22 g of a red solid with a yield of 87%. m.p.: 248.1-249.3°C. 1 H NMR (400MHz, DMSO-d 6 )δ11.43(s,1H),8.54(s,1H),8.22(s,1H),8.17(d,J=9.6Hz,1H),7.71(dd,J=15.6,10.8Hz,2H), 7.51(d, J=9.2Hz, 1H), 6.80(d, J=10.0Hz, 1H), 6.69(d, J=9.2Hz, 1H), 6.61(s, 1H), 6.48(s, 1H), 3.50(q, J=6.4Hz, 4H), 3.42(q, J=13.2Hz, 4H), 1.15(t, J=6.4Hz, 12H). 13 C NMR (100MHz, DMSO-d 6 )δ186.40,161.88,160.21,158.52,153.17,150.71,148.35,142.28,141.44,139.42,132.58,130.75,123...

Embodiment 2

[0035] The preparation of embodiment 2 test solution

[0036] (1) Preparation procedure of stock solution:

[0037] Probe QCT-O was dissolved in DMF to prepare a 1.0mmol / L stock solution. The stock solution was diluted to 10 μmol / L in methanol / water (7:3, v / v) for spectroscopic testing. The following spectral tests were all carried out in methanol / water (7:3, v / v) system. The concentration of metal ions is 10mmol / L. Prepare methanol / water (7:3, v / v) solutions with different pH values ​​and monitor them with a magnetic pH meter. After standing for 40 minutes, measure its ultraviolet absorption spectrum and fluorescence emission spectrum (500nm is the excitation wavelength). The above operation, without adding the sample solution to be tested, is the preparation of the blank test solution.

[0038] (2) Selective experiment:

[0039] Take 14 parts of 2mL methanol / water (7:3, v / v) solution, add 20 μL stock solution and different metal ions (Al 3+ , Ca 2+ ,Cr 3+ ,Mn 2+ , Fe...

Embodiment 3

[0050] Example 3 Thin-layer chromatography silica gel plate qualitatively detects mercury ions of different concentrations in the solution

[0051] Immerse the silica gel thin-layer chromatography plate in 1.0mmol / L QCT-O methanol solution, take it out after 1 minute, and evaporate the solvent at room temperature to prepare a silica gel thin-layer chromatography detection plate containing QCT-O. Immerse the detection plate in mercury ion solutions of different concentrations, take it out immediately, wait for the solvent to evaporate, and observe the color change of the thin-layer chromatography plate under natural light or a 365nm ultraviolet lamp. When the mercury ion concentration is as low as 1×10 -6 mol / L, the naked eye can see obvious color changes, such as Figure 10 .

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Abstract

The invention relates to a ratio type probe for detecting mercury ions and a preparation method and application thereof. Specifically, the invention provides a probe for detecting mercury ions, which is simple and convenient to operate and high in sensitivity. The name of the probe is 7-diethylamino-3-(3-(7-diethylamino) coumarin)-3-oxopropenyl quinoline-2-ketone, and the probe is called QCT-O for short. The QCT-O is obtained by taking 7-diethylamino-2-oxo-1, 2-dihydroquinoline-3-formaldehyde and 7-diethylaminocoumarin-3-ethanone as raw materials, and carrying out a reaction under the action of a catalyst. The probe has the advantages of fast response to mercury ions, strong selectivity and high sensitivity. In the presence of mercury ions, the color of the probe solution changes from red to yellow (under sunlight), and changes from red fluorescence to blue-green fluorescence (under an ultraviolet lamp); the absorption peak disappears at the position of 500 nm, and new absorption peaks appear at the positions of 380 nm and 440 nm; the fluorescence intensity obviously changes at the wavelength of 650 nm, the absorption and emission response intensities linearly changes with the mercury ion concentration, and the lowest detection limits are 2.62 * 10 <-8 > mol / L and 4.37 * 10 <-8 > mol / L respectively.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and analysis and detection, and in particular relates to a small molecule probe for detecting mercury ions, a preparation method thereof and an application in detecting mercury ions. Background technique [0002] Mercury ion (Hg 2+ ), as the most stable inorganic mercury, exists in natural water bodies and is one of the common toxic heavy metal ions. It can accumulate in organisms and transfer to the human body through the food chain. Trace amounts of mercury ions in the human body can directly damage important organs such as the liver and heart, causing dysfunction of the nervous system and respiratory system, and even death. At the same time, methylmercury, the methylation product of mercury ion microorganisms, can be converted into highly toxic organic mercury through the food chain. Therefore, rapid and accurate detection of mercury ions is of great significance in environmental m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/06C09K11/06G01N21/64G01N21/78
CPCC07D405/06C09K11/06G01N21/78G01N21/6428C09K2211/1029C09K2211/1088
Inventor 但飞君唐倩郭涛任双娇
Owner CHINA THREE GORGES UNIV
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