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Thiacalix[4]arene acylhydrazone Schiff base derivative and synthesis method and application thereof

A technique of aryl acyl hydrazones and Schiff bases, which is applied in the field of thiocalix[4] aryl acyl hydrazones Schiff base derivatives and their synthesis, can solve the problems of single modification structure and the like, and achieves flexible conformation and remarkable The effect of complexing ability

Inactive Publication Date: 2017-02-01
谢长江
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The problem solved in this aspect is to overcome the shortcoming of the single modification structure of the lower edge of thiocalixarene compounds, and introduce the acylhydrazone Schiff base into the lower edge of thiocalixarene

Method used

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  • Thiacalix[4]arene acylhydrazone Schiff base derivative and synthesis method and application thereof
  • Thiacalix[4]arene acylhydrazone Schiff base derivative and synthesis method and application thereof
  • Thiacalix[4]arene acylhydrazone Schiff base derivative and synthesis method and application thereof

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Embodiment 1

[0019] Example 1: Thiocalix[4]arene derivatives (compound 1)

[0020] (1) Preparation of Compound 1

[0021] Thiocalix[4]arene (4.0g, 5.6mmol) and O-(chlorobutyl)-2-hydroxyl-1-naphthaldehyde (7.4 g, 28.0mmol) in the catalyst potassium iodide (0.9g, 6.0mmol) and anhydrous Under the presence of potassium carbonate (6.0g, 43.5mmol), reflux reaction in dry acetonitrile solvent, stop after 4-5 days, suction filtration, after most of solvent is distilled under reduced pressure of filtrate, add dehydrated alcohol, find that there is solid to separate out, The resulting solid was recrystallized from chloroform / ethanol (volume ratio 3:1) to obtain a white solid with a yield of 64%. The white solid (1.6g, 1.0mmol) and 2-pyridine hydrazide (0.7g, 4.8mmol) were heated and dissolved in dry acetonitrile and dichloromethane solvents, a drop of hydrochloric acid was added dropwise as a catalyst, and stirred at room temperature for 2 days. Gradually, solids were precipitated, and the solids ...

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Abstract

The invention relates to a thiacalix[4]arene acylhydrazone Schiff base derivative and a synthesis method and application thereof. The defect that the lower-edge modifying structure of thiacalix[4]arene is single is overcome. According to the thiacalix[4]arene acylhydrazone Schiff base derivative, acylhydrazone Schiff base is introduced to the lower edge of thiacalix[4]arene to form a drooping chelating arm, and the selective complexing capability of the thiacalixarene derivative on metal ions is enhanced by means of the synergistic effect of the drooping chelating arm and thiacalixarene holes. Results of preliminary experiments on the properties of the compound show that the thiacalix[4]arene acylhydrazone Schiff base derivative has the good recognition capability on the metal ions.

Description

technical field [0001] The invention relates to a thiocalix[4]arene acylhydrazone Schiff base derivative and its synthesis method and application. Background technique [0002] The thiocalixarene that appeared in recent years is a new member of the calixarene family. Because it replaces the methylene bridge of the traditional calixarene with a sulfur atom, the rigidity and polarity of the aromatic macrocyclic structure have changed greatly. With a larger cave structure, more flexible conformation, remarkable complexing ability and easy oxidation of sulfur bridges, etc., especially the flexible conformation has aroused people's strong interest. [0003] All kinds of thiocalixarene derivatives that have been reported are usually introduced into the lower edge of the parent arene as carboxyl, amine, aliphatic, carbonyl and lone pair electron groups as chelates. therefore. The single modified structure of the lower edge limits its further application. [0004] Acylhydrazone c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/14G01N21/31
CPCC07D409/14G01N21/31
Inventor 谢长江
Owner 谢长江
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