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Compound with ferrocene aldehyde-phenylhydrazone structure as well as preparation method and application thereof

A ferrocene aldehyde and compound technology, applied in the field of electrochemical sensing materials, can solve the problems of high cost, complicated operation of acetate ions, and inability to detect with naked eyes, and achieve the effect of simple operation

Inactive Publication Date: 2013-06-26
CHANGCHUN INST OF OPTICS FINE MECHANICS & PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In order to solve the technical problems of complex operation, high cost and inability to detect with naked eyes in the existing fluorescent detection of acetate ion, the present invention proposes a compound with a ferrocenealdehyde-phenylhydrazone structure and its preparation method and application

Method used

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  • Compound with ferrocene aldehyde-phenylhydrazone structure as well as preparation method and application thereof
  • Compound with ferrocene aldehyde-phenylhydrazone structure as well as preparation method and application thereof
  • Compound with ferrocene aldehyde-phenylhydrazone structure as well as preparation method and application thereof

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preparation example Construction

[0032] The preparation method of the compound with ferrocene aldehyde-phenylhydrazone structure: Weigh ferrocene aldehyde and nitrophenylhydrazine, add them to the reaction device, reflux in an alcohol solvent with a boiling point lower than 90 ° C, cool, and filter and dry , to obtain the compound of ferrocenaldehyde-nitrophenylhydrazone structure;

[0033] The ferrocene aldehyde is ferrocene formaldehyde or 1,1'-ferrocene dicarbaldehyde;

[0034] The nitrophenylhydrazine is 2,4-dinitrophenylhydrazine or 4-nitrophenylhydrazine.

[0035] In the preparation method of the present invention, the ferrocene aldehyde and nitrophenylhydrazine are usually weighed according to the stoichiometric ratio, that is, when the raw materials are ferrocene formaldehyde and nitrophenylhydrazine, the ratio of substances is 1:1 Weigh ferrocene aldehyde and nitrophenylhydrazine. When the raw materials are 1,1'-ferrocenediformaldehyde and nitrophenylhydrazine, weigh ferrocene aldehyde and nitrophen...

Embodiment 1

[0053] Formula (I) structure (R 1 For the preparation of the compound of the ferrocene aldehyde-phenylhydrazone structure of H):

[0054] Weigh 0.21g of ferrocene formaldehyde and 0.153g of 4-nitrophenylhydrazine in 20ml of ethanol according to the stoichiometric ratio, reflux at 78°C for 2h, cool to room temperature naturally, filter the red precipitate and wash it twice with ethanol, each time Using 5ml of ethanol, the crude product was separated and purified on a silica gel column, eluted with a mixed solution of petroleum ether / ethyl acetate, evaporated the solvent, and dried to obtain a red powder, which is a compound of ferrocenaldehyde-phenylhydrazone structure.

Embodiment 2

[0056] Formula (П) structure (R 1 For the preparation of the compound of the ferrocene aldehyde-phenylhydrazone structure of H):

[0057] Weigh 0.242g of 1,1'-ferrocenedicarbaldehyde and 0.306g of 4-nitrophenylhydrazine in 30ml of ethanol according to the stoichiometric ratio, reflux at 80°C for 3h, naturally cool to room temperature, filter to obtain a red precipitate and wash with ethanol Wash twice, each time with 5ml of ethanol, the crude product is separated and purified by silica gel column, and eluted with a mixed solution of petroleum ether / ethyl acetate. Evaporate the solvent and dry to obtain a red powder, which is a compound of ferrocenealdehyde-phenylhydrazone structure.

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Abstract

The invention relates to a compound with a ferrocene aldehyde-phenylhydrazone structure as well as a preparation method and an application thereof, belonging to the technical field of an electrochemistry sensing material and solving the technical problems of complex operation, high cost and incapability of detecting with naked eyes when a conventional fluorescence manner is used for detecting acetate ions. The compound with the ferrocene aldehyde-phenylhydrazone structure is synthesized by taking ferrocene aldehyde and nitrophenylhydrazine as raw materials through aldol condensation reaction in one step. The invention also provides the application of the compound with the ferrocene aldehyde-phenylhydrazone structure serving as a visual colorimetric chemical sensor molecule in detection of the acetate ions. The compound with the ferrocene aldehyde-phenylhydrazone structure serves as the visual colorimetric chemical sensor molecule to realize the detection of the acetate ions with the naked eyes and is simple in operation, and expensive optical spectrum instruments are not needed.

Description

technical field [0001] The invention relates to a compound with a ferrocene aldehyde-phenylhydrazone structure, a preparation method and application thereof, and belongs to the technical field of electrochemical sensing materials. Background technique [0002] Anions play quite important roles in biological and chemical processes. Among many anions, acetate ion is the only carboxylate ion with a triangular structure, which can form a strong hydrogen bond. Acetic acid is an important raw material for the synthesis of daily necessities, such as nylon, paper and paint. Therefore, the invention A sensor capable of recognizing low concentrations of acetate ions has received increasing attention. [0003] Existing acetate ion sensors identify acetate ions mainly by observing changes in fluorescence intensity and red shifts. For example, Doo Ok Jang discloses a benzimidazole-based sensor (Tetrahedron Lett. 48 (2007) 8846-8850); Huang et al. synthesized a calyx aromatic hydrocarbo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02G01N21/78
Inventor 李斌陈小鹏张黎明
Owner CHANGCHUN INST OF OPTICS FINE MECHANICS & PHYSICS CHINESE ACAD OF SCI
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