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Nopinalkyl indazole silver ion fluorescence probe and preparation method thereof

A technology of nopinyl indazoles and fluorescent probes, applied in the field of fine organic synthesis

Active Publication Date: 2020-02-07
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But there is no information on the application of nopinyl indazoles to Ag + detection report

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  • Nopinalkyl indazole silver ion fluorescence probe and preparation method thereof
  • Nopinalkyl indazole silver ion fluorescence probe and preparation method thereof
  • Nopinalkyl indazole silver ion fluorescence probe and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The preparation process of nopinyl indazole compound is:

[0028]

[0029] Specific steps are as follows:

[0030] 1) Preparation of 3-(2'-pyridineformyl) nopinone:

[0031] Add 0.06 mol of sodium hydride into a three-neck flask equipped with a stirrer, thermometer and reflux condenser, slowly inject 8 mL of ethylene glycol dimethyl ether under nitrogen protection, dissolve 0.02 mol of nopinone in 9 mL of ethylene glycol dimethyl ether, and then nitrogen Slowly pour into the flask under protection, raise the temperature to control the reaction temperature at 82°C, heat to reflux for 0.5h, dissolve 0.024mol methyl picolinate in 9mL of ethylene glycol dimethyl ether, slowly inject into the flask under nitrogen protection, track the reaction by thin-layer chromatography Process, reaction 7-8h. The reaction solution was extracted 3 times with 100 mL ethyl acetate, the organic phases were combined, washed with saturated brine until neutral, the organic phase was dried o...

Embodiment 2

[0035] The solid 6,6-dimethyl-2-phenyl-3-(2′-pyridyl)-4,5,6,7-tetrahydro-2H-5,7-methanoindazole and different The metal ions were dissolved in 4-hydroxyethylpiperazineethanesulfonic acid (HEPES) buffer solution (20mM, pH=7.2, 7 / 3 (v / v) ethanol / water), and the concentration of the probe compound was prepared as 1× 10 -6 M and Ag + The concentration is 1×10 -5 19 solutions of M. Under the condition of excitation wavelength of 320nm, the fluorescence intensity changes in the presence of different metal ions were measured, such as figure 1 shown. The results showed that the compounds on Ag + It has a strong fluorescence enhancement effect, the maximum absorption wavelength is red-shifted from 455nm to 505nm, and the fluorescent color changes from blue to green under ultraviolet light, indicating that the compound has a strong effect on Ag + Has better selectivity.

Embodiment 3

[0037] The configured 6,6-dimethyl-2-phenyl-3-(2′-pyridyl)-4,5,6,7-tetrahydro-2H-5,7-methanoindazole (1×10 -6 M)+Ag + (1×10 -5 M) solution (HEPES buffer, 10mM, pH=7.2, 50% (v / v) C 2 h 5 OH) were added with Ag + Equimolar amount of K + , Na + , Mg 2+ , Fe 2+ , Fe 3+ , Mn 2+ , Ca 2+ , Al 3+ , pb 2+ , Cr 2+ ,Co 2+ , Zn 2+ , Bi 3 + , Ni 2+ , Pb 2+ , Cu 2+ , Sn 2+ , Ba 2+ , Ag + , the fluorescence spectrum was measured under the condition that the excitation wavelength was 320nm, the results are as follows figure 2 shown. When other metal ions are added, 6,6-dimethyl-2-phenyl-3-(2′-pyridyl)-4,5,6,7-tetrahydro-2H-5,7-methanomethene Kindazole-Ag + The fluorescence intensity of the complex was not affected, indicating that other metal ions did not detect Ag for the compound + make an impact.

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Abstract

The invention discloses a nopinalkyl indazole silver ion fluorescence probe and a preparation method thereof. Beta-pinene derivative nopinone which is a natural renewable resource is used as a raw material, nopinone is subjected to a Claisen condensation reaction with methyl pyridine-2-carboxylate, and 3-(2'-pyridyl formyl) nopinone is prepared; and 3-(2'-pyridyl formyl) nopinone is subjected to condensation cyclization with phenylhydrazine, and a nopinalkyl indazole compound 6,6-dimethyl-2-phenyl-3-(2'-pyridyl)-4,5,6,7-tetrahydro-2H-5,7-endomethylene indazole is obtained. The compound as a specific fluorescence probe molecule has good application in the aspect of silver ion detection.

Description

technical field [0001] The invention belongs to the technical field of fine organic synthesis, and relates to a nopinyl indazole fluorescent probe molecule, a preparation method thereof and an application in detecting silver ions. Background technique [0002] As a widely distributed resource, silver-containing compounds are widely used in many industrial production activities, such as metallurgical industry, pharmaceutical industry, electroplating industry, and food industry. Every year, industrial sewage containing a large amount of silver ions flows into rivers and lakes, while low concentrations of silver ions accumulate in marine organisms, causing harm to humans at the top of the food chain. Silver ions have a serious impact on the human nervous system, liver, and bones, causing many diseases. Therefore, silver ions are regarded as the most toxic metal ion. Therefore, the development of highly selective and sensitive detection Ag + The method is of great significanc...

Claims

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Application Information

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IPC IPC(8): C07D401/04C09K11/06G01N21/64
CPCC07D401/04C09K11/06G01N21/643C09K2211/1007C09K2211/1029C09K2211/1044
Inventor 王石发姜倩徐徐李明新杨益琴王芸芸谷文徐海军卞天岑
Owner NANJING FORESTRY UNIV
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