A calix[4]arene derivative containing both azo and Schiff base groups at the lower edge and its synthesis method and application

A technology of arene derivatives and Schiff base groups, which is applied in the field of new calix[4]arene derivatives and their synthesis, can solve the problem of single modification structure, etc., and achieve simple synthesis routes, high yields, and mild reaction conditions Effect

Active Publication Date: 2015-10-28
LIAONING UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The problem solved by the present invention is to overcome the shortcoming of the single modification structure of the lower edge of the calixarene compound, and combine the Schiff base and the azo group in the same branch of the lower edge of the calixarene

Method used

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  • A calix[4]arene derivative containing both azo and Schiff base groups at the lower edge and its synthesis method and application
  • A calix[4]arene derivative containing both azo and Schiff base groups at the lower edge and its synthesis method and application
  • A calix[4]arene derivative containing both azo and Schiff base groups at the lower edge and its synthesis method and application

Examples

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Effect test

example 1

[0027] Example 1: Calix [4] arene derivatives (compounds 1-8)

[0028] (1) Preparation of compound 6

[0029] The name of compound 6: 25,27-dihydroxy-26,28-di{2-[2-(N-(2-methyl-4-(2′-methylphenylazo)phenyl)imino ) methylenephenoxy]ethoxy}calix[4]arene.

[0030] Preparation method: Add dibromocalix[4]arene (0.5mmol), salicylaldehyde (1.5mmol), sodium hydroxide (1mmol), and 40ml of acetonitrile into a 100ml round-bottomed flask in sequence, and react at reflux temperature. Thin layer chromatography followed the progress of the reaction. After the reaction stopped, it was filtered with suction, and the obtained solid was dissolved in 20 ml of dichloromethane, washed twice with water, and dried overnight with anhydrous sodium sulfate. Filter out inorganic salts, evaporate part of the organic solvent and cool, and use CH 2 Cl 2 / CH 3 After recrystallization from OH (volume ratio 3:1), chromatographic separation gave light yellow crystals with a yield of 67.5%. Take the light...

example 2

[0046] Example 2: Calix [4] arene derivatives (compounds 9-12)

[0047] (1) Preparation of Compound 9

[0048] Nomenclature of compound 9: 25,27-dihydroxy-26,28-bis{2-[3-(N-(4-phenylazophenyl)imino)methenylphenoxy]ethoxy} p-tert-Butylcalix[4]arene

[0049] Preparation method: Add dibromo-p-tert-butylcalix[4]arene (0.5mmol), m-hydroxybenzaldehyde (1.5mmol), potassium hydroxide (1mmol), and 40ml of acetonitrile into a 100ml round-bottomed flask in turn, reflux reaction, thin Layer chromatography followed the progress of the reaction. After the reaction stopped, filter with suction. The resulting solid was dissolved in 20 ml of chloroform, washed twice with water, and dried overnight over anhydrous sodium sulfate. Filter out the inorganic salts, evaporate part of the organic solvent and cool, and use CHCl for the crude product 3 / C 2 h 5 OH (volume ratio 3:1) was recrystallized and chromatographically separated to obtain white crystals with a yield of 60.5%. Take the whit...

example 3

[0063] Example 3: Calix[4]arene derivatives (compounds 13-16)

[0064] (1) Preparation of Compound 15

[0065] The name of compound 15: 25,27-dihydroxy-26,28-bis{2-[3-(N-(2′-chlorophenylazo)imino)methylenephenoxy]ethoxy} Calix[4]arene

[0066] Preparation method: Dibromocalix[4]arene (0.5mmol), m-hydroxybenzaldehyde (1.5mmol), potassium carbonate (0.5mmol), 20ml each of pyridine and acetonitrile were sequentially added to a 100ml round bottom flask, reflux reaction, thin Layer chromatography followed the progress of the reaction. After the reaction stopped, filter with suction. The resulting solid was dissolved in 20 ml of dichloromethane, washed twice with water, and dried overnight over anhydrous sodium sulfate. Filter out inorganic salts, evaporate part of the organic solvent and cool, and use CH 2 Cl 2 / CH 3 OH (volume ratio 3:1) was recrystallized and chromatographically separated to obtain white crystals with a yield of 60.31%. Take the white crystal (0.1mmol), 2...

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Abstract

The invention relates to a novel calix[4]arene derivative of which lower edge simultaneously containing azo and schiff base groups and its synthesis method and use. The novel calix[4]arene derivative solves the problem of a single lower-edge modification structure of the calix[4]arene. The synthesis method creatively realizes bonding of the azo and schiff base groups to the same branched chain of the lower edge of the calix[4]arene so that a pendulous chelating arm is formed and is shown in the structural formula [I]. Through synergism of the pendulous chelating arm and the calixarene cavity, the selective complexation of the obtained calixarene derivative and metal ions is improved. According to a color change of main molecules in the reaction, complexation effect generation is monitored. The result of a preliminary experiment on the derivative compound properties shows that some of the derivative compounds have good metal ion identification functions.

Description

technical field [0001] The invention relates to a novel calix[4]arene derivative whose lower edge contains both azo and Schiff base groups as pendant chelating arms, a synthesis method and application thereof. Background technique [0002] Calixarenes are the "third generation supramolecules" after crown ethers and cyclodextrins. By controlling different reaction conditions, the cavity size of calixarene can be changed, and various selective functionalization can be carried out on the upper edge, lower edge and methylene connected to the benzene ring of calixarene to obtain a variety of highly selective sexual subject matter. [0003] All kinds of calixarene derivatives that have been reported are usually introduced into the lower edge of the parent calixarene such as carboxyl, amine, ester, carbonyl and other groups containing lone electron pairs as chelating groups, and then introduced Chromophores. Therefore, the lower edge modification structure is single, which limit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C251/24C07C249/02G01N21/78
Inventor 范平徐生明李薇薇陈辰祃艳强
Owner LIAONING UNIVERSITY
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