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Fluorescent probe for detecting mercury ions, preparation method thereof, and application method thereof

A fluorescent probe, mercury ion technology, used in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc. Detection, low cost effect

Active Publication Date: 2019-11-22
ZHEJIANG SCI-TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, current probes based on thioacetals or thioamides as probe reporter groups (see review Mahato, P.; Saha, S.; Das, P.; Agarwalla H.; Das, Amitava. RSC Adv. ,2014,4,36140–36174.) often use coumarin, fluorescein, BODIPY, rhodamine, etc. Penetrate the deep tissue of organisms, which is not conducive to accurate detection in complex biological systems
In addition, the detection limit of current mercury ion fluorescent probes is relatively high, and it is difficult to quantitatively detect trace or even extremely trace amounts of mercury ion samples.

Method used

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  • Fluorescent probe for detecting mercury ions, preparation method thereof, and application method thereof
  • Fluorescent probe for detecting mercury ions, preparation method thereof, and application method thereof
  • Fluorescent probe for detecting mercury ions, preparation method thereof, and application method thereof

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Experimental program
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Effect test

Embodiment 1

[0037] Embodiment 1, the synthesis of compound TPL1

[0038] Compound 3'-(diethylamino)-6'-((4-methoxyphenyl)ethynyl)-3H-spiro[isobenzofuran-1,9'-xanthene]-3-one ( 3) Synthesis of

[0039] 4g 3'-(diethylamino)-6'-iodo-3H-spiro[isobenzofuran-1,9'-xanthene]-3-one (1) (8mmol), 80mg cuprous iodide (0.4mmol), 0.16g bis(triphenylphosphine)palladium dichloride (0.2mmol) and 20mL triethylamine were dissolved in 60mL tetrahydrofuran, and 1.3g 4-ethynyl anisole (9.6mmol) was added to react at room temperature 4 After one hour, the reaction solution was filtered with diatomaceous earth, the solvent was spin-dried, washed with ethanol, and dried to obtain the compound 3'-(diethylamino)-6'-((4-methoxyphenyl)ethynyl)- 3H-spiro[isobenzofuran-1,9'-xanthene]-3-one (3), this compound can be directly used in the next reaction.

[0040] Compound 2-amino-3'-(diethylamino)-6'-((4-methoxyphenyl)ethynyl)spiro[isoindoline-1,9'-xanthene]-3- Synthesis of Ketone (4)

[0041]25g compound 3'-(diethyla...

Embodiment 2

[0045] Embodiment 2, the color response of compound TPL1 to mercury ion

[0046] A test mother liquid solution of dimethyl sulfoxide (DMSO) of the fluorescent probe TPL1 for detecting mercury ions according to the present invention with a concentration of 1 mM was prepared for use. Measure 10 μL of this mother solution and add it dropwise to a phosphate buffer solution with a certain concentration of mercury ions, and use the corresponding phosphate buffer solution to adjust the volume to 10 mL, so that in the test solution, the concentration of the probe is 1.0 μM, and the concentration of mercury ions is 10.0 μM for color response testing. Such as figure 2 and 3 As shown, after adding the mercury ion aqueous solution, the color of the solution was observed to change from colorless to red, and the fluorescence of the solution also changed from almost no fluorescence to bright red fluorescence, indicating that the probe TPL1 has an intuitive color response to mercury ions ...

Embodiment 3

[0047] Embodiment 3, the ultraviolet titration detection of different concentrations of mercury ions to compound TPL1

[0048] A test mother liquid solution of dimethyl sulfoxide (DMSO) of the fluorescent probe TPL1 for detecting mercury ions according to the present invention with a concentration of 1 mM was prepared for use. Measure 10 μL of this mother solution and add it dropwise to phosphate buffer with different concentrations of mercury ions, and use the corresponding phosphate buffer to make up to 10 mL, so that in the test solution, the concentration of the probe is 1.0 μM, and the concentration of mercury ions is 0-3.0μM for absorption spectrum test. The ultraviolet absorption curves in each system were obtained, and the standard curves of absorbance and mercury ion concentration were established. Such as Figure 4 As shown, as the mercury ion concentration increases, the absorbance at 526nm increases gradually, and has a good linear relationship with the mercury i...

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Abstract

The invention discloses a fluorescent probe for detecting mercury ions, a preparation method thereof, and an application method thereof. A novel fluorescence system with two-photon emission is constructed by using xanthene and benzyne, a mercury-ion identification portion is directly introduced in a portion of a meso-position spiral ring such that the mercury-ion identification portion can specifically respond to the mercury ions. A conjugate system of the probe is destroyed by the presence of meso-position thiosemicarbazide and has no fluorescence emission. However, in the presence of the mercury ions, due to an intramolecular desulfurization cyclization reaction promoted by the mercury ions, the meso-position spiral ring is opened, and probe molecules emit strong red fluorescence. The 'on-off' type mercury ion probe constructed by the xanthene and benzyne provided by the present invention has a good response to a mercury-ion solution, the sensitive and quantitative detection of tracemercury ions in a sample can be realized, and the probe has the advantages of simple operation, low cost, sensitive response, and easy popularization and application.

Description

technical field [0001] The invention belongs to the field of small organic molecule fluorescent probes, and specifically relates to a xanthene derivative used as a mercury ion fluorescent probe, a preparation method and a use method thereof. Background technique [0002] Mercury is a heavy metal widely distributed in air, water and soil with severe physiological toxicity. Elemental mercury and mercury ions can be converted into methylmercury by microorganisms, and further enter the food chain through various channels, accumulate in the organism and finally enter the human body, causing great damage to the brain, central nervous system and other systems of the human body , can cause serious diseases such as language and memory impairment, and even lead to the death of the organism. In recent years, with the frequent application of mercury in industrial production, the environmental pollution and the resulting biological hazards have become increasingly serious. Therefore, t...

Claims

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Application Information

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IPC IPC(8): G01N21/64C07D491/107C09K11/06
CPCC07D491/107C09K11/06C09K2211/1033G01N21/6402
Inventor 韩益丰陈舒欣秦思瑶章世深汪玲
Owner ZHEJIANG SCI-TECH UNIV