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High-sensitivity fluorescent probe for detecting Hg<2+>, preparation method and application thereof

A fluorescent probe, high-sensitivity technology, applied in the field of high-sensitivity fluorescent probes for detecting Hg2+ and their preparation, can solve the problems of low sensitivity and the like

Active Publication Date: 2020-10-27
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of these fluorescent probes require the participation of organic solvents to detect mercury ions and have low sensitivity.

Method used

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  • High-sensitivity fluorescent probe for detecting Hg&lt;2+&gt;, preparation method and application thereof
  • High-sensitivity fluorescent probe for detecting Hg&lt;2+&gt;, preparation method and application thereof
  • High-sensitivity fluorescent probe for detecting Hg&lt;2+&gt;, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] N'-(4'-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-5,7-methanoindazol-3-yl)-[1,1' Preparation of -biphenyl]-4-methylene)pyridine-2-carbohydrazide

[0036] 1) Preparation of 3-(4-bromobenzoyl)nopinone:

[0037] Add 3mmol nopinone, 3.6mmol methyl 4-bromobenzoate, 9mmol sodium hydride and 60mL ethylene glycol dimethyl ether into a three-necked flask in turn, heat and reflux reaction under nitrogen protection, and react for about 8 hours until the conversion rate of nopinone Up to 95% or more (TLC tracking detection). After the reaction solution was cooled, 30 mL of deionized water was added to quench the reaction, and then extracted 3 times with 0.3 L of ethyl acetate, and the combined organic phase was washed several times with saturated brine until neutral, dried over anhydrous sodium sulfate, and filtered , the solid product obtained after concentration, and then washed with a small amount of ethyl acetate to obtain 3-(4-bromobenzoyl)nopinone, with a yield of 62.1% and a puri...

Embodiment 2

[0045] N'-(4'-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-5,7-methanoindazol-3-yl)-[1,1 '-Biphenyl]-4-methylene)pyridine-2-carboxylhydrazide was dissolved in DMF to prepare a solution with a concentration of 1 mM, and diluted to 10 μM with PBS buffer solution (pH=7.4, 10 mM) for use. Different metal ions were dissolved in deionized water and diluted to 100 μM for use, and different metal ion pairs N'-(4'-(6,6-dimethyl-4,5,6, Fluorescence spectrum of 7-tetrahydro-1H-5,7-methanoindazol-3-yl)-[1,1′-biphenyl]-4-methylene)pyridine-2-carboxhydrazide, Such as figure 1 shown. The results showed that, compared to other metal ions, only Hg 2+ It can cause obvious changes in the fluorescence spectrum of the compound, indicating that the compound can specifically recognize Hg 2+ .

Embodiment 3

[0047] N'-(4'-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-5,7-methanoindazol-3-yl)-[1,1 '-Biphenyl]-4-methylene)pyridine-2-carboxylhydrazide was dissolved in DMF to prepare a solution with a concentration of 1 mM, and then diluted to 10 μM with PBS buffer solution (pH=7-4, 10 mM) for use. Also Hg 2+ Dissolve in PBS buffer solution to prepare solutions with concentrations of 0, 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 2, 4, 6, 8, 10, 15, 20 μM. The different concentrations of Hg were measured by fluorescence spectrometry 2+On N'-(4'-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-5,7-methanoindazol-3-yl)-[1,1 The fluorescence spectrum of '-biphenyl]-4-methylene)pyridine-2-carbohydrazide, such as figure 2 shown. The results showed that the fluorescence intensity of the compound at around 460nm was obviously quenched gradually, indicating that the compound could be used as a tool for detecting Hg 2+ fluorescent probes.

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Abstract

The invention discloses a high-sensitivity fluorescent probe for detecting Hg<2+>, a preparation method and application thereof. The N'-(4'-(6, 6-dimethyl-4, 5, 6, 7-tetrahydro-1H-5, 7-bridge methylene indazole-3-yl)-[1, 1'-biphenyl]-4-methylene)pyridine-2-formylhydrazine is prepared by taking a natural renewable resource beta-pinene derivative nopinone as a raw material. The compound can be selectively complexed with Hg<2+>, cyan fluorescence of the compound is rapidly quenched, the detection limit reaches 17nM, and the compound can be used as a specific fluorescent probe for detecting Hg<2+>and has good application value.

Description

technical field [0001] The invention belongs to the technical field of fine organic synthesis and relates to a method for detecting Hg 2+ Highly sensitive fluorescent probe and its preparation method. Background technique [0002] Mercury ion (Hg 2+ ) is a highly toxic heavy metal ion widely distributed in soil, rivers, lakes, groundwater and industrial wastewater. Hg 2+ It is easy to enter the organism through bioaccumulation. Once the human body ingests excessive mercury ions, it will cause serious damage to its nerves, internal organs, and genetic genes. Therefore, the development of fast, convenient, high sensitivity and high selectivity for the detection of Hg 2+ The method is very important in environmental analysis. [0003] In recent years, there have been some studies on the synthesis of organic fluorescent probes and their use in Hg 2+ According to the different structures of the luminescent groups of fluorescent probes, detection reports usually include: flu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12C09K11/06G01N21/64
CPCC07D401/12C09K11/06C09K2211/1022C09K2211/1029C09K2211/1044G01N21/6428G01N2021/6432
Inventor 王石发李明新杨海燕巩帅王忠龙张燕徐徐杨益琴徐海军
Owner NANJING FORESTRY UNIV
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