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Fluorescence probe based on triazole acyl hydrazone derivative and preparation method of fluorescence probe

A technology of triazole acyl hydrazone and fluorescent probe, which is applied in the fields of fluorescence/phosphorescence, chemical instruments and methods, and luminescent materials, and can solve problems such as the toxicity of aluminum ions, achieve strong selectivity, easily obtain raw materials, and realize naked-eye discrimination Detection effect

Inactive Publication Date: 2018-05-01
HENAN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Fluorescence probe based on triazole acyl hydrazone derivative and preparation method of fluorescence probe
  • Fluorescence probe based on triazole acyl hydrazone derivative and preparation method of fluorescence probe
  • Fluorescence probe based on triazole acyl hydrazone derivative and preparation method of fluorescence probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The synthesis diagram of triazole acylhydrazone derivatives is shown in figure 1 .

[0031] Dissolve 1.93g of 4-diethylamino salicylaldehyde in 30mL of absolute ethanol, then add 1.27g of 1,2,4-triazole-3-carboxylhydrazide, reflux and stir for 2 hours under normal pressure, and precipitate a large amount of The solid was filtered under reduced pressure, and the filter residue was washed with absolute ethanol to obtain a light yellow solid, which was the target product, and the yield of the target product was 79%.

[0032] The crystal structure of triazole acylhydrazone derivative hydrate is shown in figure 1 ;

[0033] Adopt nuclear magnetic resonance instrument to carry out nuclear magnetic resonance analysis to the prepared triazole acyl hydrazone derivatives, the results are as follows:

[0034] 1 H NMR (400MHz, DMSO-d 6 ),δ(ppm):14.79(s,1H,OH),12.13(s,1H,NH),11.41(s,1H,NH-triazole),8.62(s,1H,CH-triazole),8.54(s ,1H,CH=N),7.14-7.16(d,1H,Aryl-H),6.26-6.29(dd,1H,...

Embodiment 2

[0037] Dissolve 3.86g of 4-diethylamino salicylaldehyde in 80mL of 75% ethanol, then add 2.54g of 1,2,4-triazole-3-carboxylhydrazide, reflux and stir for 4 hours under normal pressure, and precipitate a large amount of solid after cooling to room temperature , filtered under reduced pressure, and the filter residue was washed with 75% ethanol to obtain a light yellow solid, which was the target product, and the yield of the target product was 85%.

Embodiment 3

[0039] Dissolve 3.86g of 4-diethylamino salicylaldehyde in 80mL of absolute ethanol, then add 2.54g of 1,2,4-triazole-3-carboxylhydrazide, reflux and stir for 3 hours under normal pressure, and precipitate a large amount of The solid was filtered under reduced pressure, and the filter residue was washed with absolute ethanol to obtain a pale yellow solid, which was the target product, and the yield of the target product was 82%.

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Abstract

The invention provides a fluorescence probe based on a triazole acyl hydrazone derivative and a preparation method of the fluorescence probe. The chemical structural formula of the triazole acyl hydrazone derivative is as follows. The triazole acyl hydrazone derivative provided by the invention can selectively react with aluminum ions, and weak fluorescence is changed into blue fluorescence. A colorimetric fluorescence enhancement effect is achieved, naked eye discrimination detection can be realized, and particularly an application that the triazole acyl hydrazone derivative is used as the fluorescence probe to conveniently detect aluminum ions in a cell can be realized.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to triazole acylhydrazone derivatives and their preparation methods and applications. 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 detect complex systems. Acylhydrazone de...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/10C09K11/06G01N21/64
Inventor 王元吴伟娜赵晓雷吴浩
Owner HENAN POLYTECHNIC UNIV
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