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Fluorescent probe based on pyridine bipyrazole acylhydrazone derivatives and its preparation method and application

A technology of pyridine bipyrazole acylhydrazone and fluorescent probe, which is applied in the fields of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of aluminum ion toxicity, etc., and achieve strong selectivity and high selectivity fluorescence recognition performance , the effect of easy access to raw materials

Inactive Publication Date: 2020-10-02
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 pyridine bipyrazole acylhydrazone derivatives and its preparation method and application
  • Fluorescent probe based on pyridine bipyrazole acylhydrazone derivatives and its preparation method and application
  • Fluorescent probe based on pyridine bipyrazole acylhydrazone derivatives and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Synthesis of Pyridine Bipyrazole Hydrazone Derivatives

[0027]

[0028] Dissolve 1.93g of 4-diethylamino salicylaldehyde in 100mL ethanol / DMF (1:1, v:v), then add 2.03g of 5-(3-pyridyl)pyrazole-3-carboxylhydrazide, and reflux under normal pressure After stirring for 2 h, 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) to obtain a light yellow solid, which was the target product, and the yield of the target product was 85%.

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

[0030] 1 HNMR (400MHz, DMSO-d 6 ), δ (ppm): 13.99 (s, 1H, NH-pyrazole), 11.83 (s, 1H, NH), 11.18 / 11.54 (1H, OH), 9.06 (s, 1H, CH=N), 8.58 (s ,1H,Aryl-H),8.49(s,1H,Aryl-H),8.21(s,1H,Aryl-H),7.52(s,1H,Aryl-H),7.37(s,1H,Aryl-H )7.17(s,1H,Aryl-H...

Embodiment 2

[0033] Dissolve 3.86g of 4-diethylamino salicylaldehyde in 200mL ethanol / DMF (1:2, v:v) solution, then add 4.06g of 5-(3-pyridyl)pyrazole-3-carboxylhydrazide, under normal pressure After stirring under reflux for 4 h, a large amount of solid precipitated after cooling to room temperature, 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 73%.

Embodiment 3

[0035] Dissolve 3.86g of 4-diethylamino salicylaldehyde in 200mL ethanol / DMF (1:1, v:v) solution, then add 4.06g of 5-(3-pyridyl)pyrazole-3-carboxhydrazide, under normal pressure Reflux and stir for 3 hours, after cooling to room temperature, a large amount of solids 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 85% .

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Abstract

The present invention provides a fluorescent probe based on a pyridylpyrazole acylhydrazone derivative, a preparation method and applications thereof, wherein the chemical structure formula of the pyridylpyrazole acylhydrazone derivative is defined in the specification. According to the present invention, the pyridylpyrazole acylhydrazone derivative can selectively interact with aluminum ions to change weak fluorescence into blue fluorescence so as to provide the colorimetric fluorescence enhancing effect, such that the naked eye discrimination detection can be achieved, and the applications of the pyridylpyrazole acylhydrazone derivative as the fluorescent probe in the convenient detection of intracellular aluminum ions can be achieved.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to a fluorescent probe based on pyridine 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 de...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04C09K11/06G01N21/64
CPCC07D401/04C09K11/06C09K2211/1044G01N21/6486
Inventor 王元吴伟娜李慧军吴浩
Owner HENAN POLYTECHNIC UNIV
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