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5,11,17,23-tetra-sulfonic azo phenyl calyx [4] arene, and preparation and use thereof

A technology for tetrasulfonic acid azophenyl calix and calixarene, which is applied in 5 fields, can solve problems such as no reports on aromatics being found, and achieve the effects of reducing the difficulty of purification, simple operation and mild reaction conditions

Inactive Publication Date: 2009-08-12
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] However, azophenylcalix[4]arene sulfonate has not been found and reported

Method used

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  • 5,11,17,23-tetra-sulfonic azo phenyl calyx [4] arene, and preparation and use thereof
  • 5,11,17,23-tetra-sulfonic azo phenyl calyx [4] arene, and preparation and use thereof

Examples

Experimental program
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Embodiment 1

[0033] (1) Preparation of benzenesulfonic acid diazonium salt solution:

[0034] Dissolve 1.73g (10mmol) of p-aminobenzenesulfonic acid in 10mL of 5% (mass fraction) sodium hydroxide solution, add 0.69g (10mmol) sodium nitrite after cooling to room temperature, continue stirring for 30 minutes, and then dissolve the above solution Slowly add it dropwise to the mixture of 5mL concentrated hydrochloric acid and 3mL distilled water under stirring, keeping the temperature at 0-5°C. After the dropwise addition is completed, stir for another 30 minutes. Afterwards, a large amount of white precipitate is found, and 4mL distilled water is added. After dissolving.

[0035] (2) see figure 1 , to prepare 5,11,17,23-tetrasulfonic acid azophenylcalix[4]arene:

[0036] Then the above-mentioned azo salt solution was slowly added dropwise to 26 mL of N, N'-dimethylformamide and methanol mixed with 1 g (2.36 mmol) calix [4] arene and 4.08 g (30 mmol) sodium acetate (N, N'-dimethylformamide:...

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Abstract

The invention discloses a 5,11,17,23-tetrasulfonic acid azophenyl calyx[4] aromatic hydrocarbon compound. Fourtetrasulfonic acid azobenzenes are introduced into a contraposition of calyx[4] aromatic hydrocarbon hydroxyl. The preparation method of the compound is as below: diazonium salt solution is slowly dripped into a solution in which calyx[4] aromatic hydrocarbon is dissolved; the color of the solution changes into red from achromaticity, and a small amount of red precipitate is generated; standing is carried out for 2-4 h; pH value is adjusted to be neutral; and 5,11,17,23-tetrasulfonic acid azophenyl calyx[4] aromatic hydrocarbon is obtained after the procedures of filtration, recrystallization, washing and drying. The compound can be used as a new pH-indicator and can be used for identifying metal ions and synthesizing metal compositions and metal polymers. The preparation method of the compound has the advantage of mild reaction condition and does not need the protection of an inert gas.

Description

technical field [0001] The invention relates to a calixarene derivative containing an azo group and a preparation method thereof, in particular to 5,11,17,23-tetrasulfonic acid azophenyl calix[4]arene, a preparation method and application thereof. Background technique [0002] In recent years, due to the good water solubility of calixarene sulfonate, it has potential and broad application prospects in many fields such as the separation of neutral organic matter, sewage treatment, phase transfer catalysis, and enzyme model reactions. [0003] At the same time, because the azo group has good fluorescence, ultraviolet, cis-trans isomerism and other characteristics, the introduction of the azo group into the upper edge of the calixarene has attracted widespread attention. At present, there are some azo-containing Group calixarene derivatives have been reported: [0004] (1) Prepare carboxy azobenzene calix [4] arene with calix [4] arene and benzoic acid diazonium salt as reacta...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/46C07C303/22G01N31/22
Inventor 郎建平刘雷雷陈阳任志刚李红喜
Owner SUZHOU UNIV
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