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Fluorescent probe based on pyrazine bipyrazole acylhydrazone derivative and its preparation method and application

A pyrazine bipyrazole acyl hydrazone, fluorescent probe technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as aluminum ion toxicity, achieve strong selectivity, high sensitivity, wide potential The effect of applying value

Inactive Publication Date: 2020-07-28
HENAN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in recent years, more and more evidences have proved that aluminum ions have great toxicity to the human central nervous system.

Method used

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  • Fluorescent probe based on pyrazine bipyrazole acylhydrazone derivative and its preparation method and application
  • Fluorescent probe based on pyrazine bipyrazole acylhydrazone derivative and its preparation method and application
  • Fluorescent probe based on pyrazine bipyrazole acylhydrazone derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Synthesis of Pyrazine Bipyrazole Hydrazone Derivatives

[0027]

[0028] Dissolve 1.22g of salicylaldehyde in 100mL ethanol / DMF (1:1, v:v), then add 2.04g of 5-(2-pyrazinyl)pyrazole-3-carboxylhydrazide, stir under reflux for 2h under normal pressure, and cool After reaching room temperature, a large amount of solid was precipitated, filtered under reduced pressure, and the filter residue was washed with ethanol / DMF (1:1, v:v) to obtain a light yellow solid, which was the target product, and the yield of the target product was 84%.

[0029] Adopt nuclear magnetic resonance instrument to carry out nuclear magnetic resonance analysis to the pyrazine bipyrazole acyl hydrazone derivative that makes, the result is as follows:

[0030] 1 H NMR (400MHz, DMSO-d 6 ),δ(ppm):41.35-14.42(1H,NH-pyrazole), 12.23(s,1H,NH),10.99 / 11.42(1H,OH),9.24 / 9.29(1H,CH=N),8.67-8.73 (m,3H, Aryl-H),7.48-7.70(m,2H,Aryl-H),7.29-7.33(m,1H,Aryl-H),6.91-6.96(m,2H,Aryl-H), specific NMR spectrum see ...

Embodiment 2

[0033] Dissolve 2.44g of salicylaldehyde in 200mL of ethanol / DMF (1:2, v:v) solution, then add 4.08g of 5-(2-pyrazinyl)pyrazole-3-carboxylhydrazide, and stir under reflux for 4h under normal pressure, After cooling to room temperature, a large amount of solids were precipitated, filtered under reduced pressure, and the filter residue was washed with ethanol / DMF (1:2, v:v) to obtain a light yellow solid, which was the target product, and the yield of the target product was 78%.

Embodiment 3

[0035] Dissolve 2.44g of salicylaldehyde in 200mL of ethanol / DMF (1:1, v:v) solution, then add 4.08g of 5-(2-pyrazinyl)pyrazole-3-carboxylhydrazide, reflux and stir for 3h under normal pressure, After cooling to room temperature, a large amount of solid precipitated, filtered under reduced pressure, and the filter residue was washed with ethanol / DMF (1:1, v:v) solution to obtain a light yellow solid, which was the target product, and the yield of the target product was 88%.

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Abstract

The invention provides a pyrazinazole acylhydrazone derivative-based fluorescence probe, and a preparation method and application thereof. The chemical structural formula of the pyrazinazole acylhydrazone derivative is shown in the specification. The pyrazinazole acylhydrazone derivative provided by the invention can interact with aluminum ions selectively, is changed from weak fluorescence into blue fluorescence, has a colorimetric fluorescence enhancing effect, can realize naked eye discrimination detection, and is particularly applied as a fluorescence probe for convenience detection of intracellular aluminum ions.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a fluorescent probe based on pyrazine bipyrazole acylhydrazone derivatives, a preparation method and application thereof. Background technique [0002] Aluminum is the most abundant metal element in the earth's crust, and is widely used in aerospace, automobile industry, metallurgy and chemical industry, agricultural production, and daily life. But in recent years, more and more evidences have proved that aluminum ions have great toxicity to the human central nervous system. Therefore, it is of great significance to study sensors with high selectivity and high sensitivity for detecting aluminum ions. [0003] In recent years, fluorescent molecular probe technology has become an important means to detect metal ion pollution due to its high sensitivity, simple operation, and low cost. Fluorescence-enhanced sensing materials can reduce detection errors and accurately d...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/04C09K11/06G01N21/64
CPCC07D403/04C09K11/06C09K2211/1007C09K2211/1044G01N21/64G01N2021/6417
Inventor 王元吴伟娜于亚平李珊珊寇凯刘树阳赵玲玲
Owner HENAN POLYTECHNIC UNIV
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