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8-hydroxyquinoline functionalized pillar[5]arene and synthesis thereof, and application of 8-hydroxyquinoline functionalized pillar[5]arene in detection and adsorption of ethylenediamine

A hydroxyquinoline, functionalized technology, applied in chemical instruments and methods, organic chemistry, measuring devices, etc., can solve problems such as expensive

Active Publication Date: 2021-07-27
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods are either expensive (using rare-earth metals such as La or Ce) or require special solutions, so there is an urgent need to construct chemical materials that detect adsorbed ethylenediamine through fluorescence changes.

Method used

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  • 8-hydroxyquinoline functionalized pillar[5]arene and synthesis thereof, and application of 8-hydroxyquinoline functionalized pillar[5]arene in detection and adsorption of ethylenediamine
  • 8-hydroxyquinoline functionalized pillar[5]arene and synthesis thereof, and application of 8-hydroxyquinoline functionalized pillar[5]arene in detection and adsorption of ethylenediamine
  • 8-hydroxyquinoline functionalized pillar[5]arene and synthesis thereof, and application of 8-hydroxyquinoline functionalized pillar[5]arene in detection and adsorption of ethylenediamine

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Experimental program
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Effect test

Embodiment 1

[0032] The synthesis of embodiment 1 PQ8

[0033] (1) Synthesis of M4 (name): Hydroquinone (2.20g, 20mmol), KI (6.64g, 40mmol), K 2 CO 3 (13.82 g, 100 mmol) and 1.4-dibromobutane (17.27 g, 80 mmol) were sequentially added to acetone (250.0 mL) solution. The reaction mixture was refluxed at 85 °C for 72 h under nitrogen atmosphere. The solvent was then removed under reduced pressure. The target compound was separated by column chromatography (eluent: petroleum ether / ethyl acetate = 50:1, v / v). The final target product M4 was a white solid. Yield: 55%, melting point: 83~85°C.

[0034] (2) Synthesis of double-sided 1.4-dibromobutane modified columnarene: M4 (1.90g, 5mmol), 1.4-dimethoxybenzene (6.90g, 20mmol) and paraformaldehyde (2.50g, 25mmol) were added in 1.2 - in dichloroethane (250.0 mL) solution. After stirring at 30°C for 30min, add BF dropwise 3 O.(C 2 h 5 ) 2 , A total of 6.5 mL was added dropwise. After the color of the solution changed to dark green, add 1...

Embodiment 2

[0038] Embodiment 2 PQ8 is to the detection of EDA

[0039] The solid powder of 10mg PQ8 was weighed and exposed to organic volatile compounds acetonitrile, dichloromethane, chloroform, formaldehyde, pyridine, tetrahydrofuran, ammonia water, n-propylamine, n-butylamine, 1.6-hexamethylenediamine, 1.10-decanediamine and In the vapor of ethylenediamine, if the fluorescent color of PQ8 changes from blue to light yellow, it indicates that the organic volatile compound is ethylenediamine; if the fluorescent color of PQ8 does not change significantly, it indicates other organic volatile compounds.

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Abstract

The invention provides 8-hydroxyquinoline functionalizedpillar[5]arene. The 8-hydroxyquinoline functionalizedpillar[5]arene (PQ8) is a white solid obtained by taking acetonitrile as a solvent, bilateral 1,4-dibromobutane modified pillararene and 8-hydroxyquinoline as reaction substrates, performing reacting at 80-85 DEG C for 70-72 hours under the action of K2CO3 and KI and the protection of N2 and carrying out separating by column chromatography after the reaction is finished. The PQ8 solid powder is exposed in steam of acetonitrile, dichloromethane, chloroform, formaldehyde, pyridine, tetrahydrofuran, ammonia water, n-propylamine, n-butylamine, 1,6-hexamethylenediamine, 1,10-decamethylene diamine and ethidene diamine, and only the steam of ethidene diamine enables the fluorescence color of the solid powder of the 8-hydroxyquinoline functionalized pillar[5]arene to change from blue to faint yellow, so single selective detection of ethylenediamine can be realized; and meanwhile, the PQ8 can realize the adsorption of the ethanediamine, and the molar adsorption rate of the ethanediamine can reach 176.19%.

Description

technical field [0001] The present invention relates to a kind of 8-hydroxyquinoline functionalized column [5] arene and its synthesis method; the present invention also relates to the application of 8-hydroxyquinoline functionalized column [5] arene in detection and adsorption of ethylenediamine, The invention belongs to the fields of chemical synthesis, VOCs detection and adsorption. Background technique [0002] Ethylenediamine (EDA, C 2 h 6 N 2 ) is a common volatile organic compound, which is mainly used in polymer resin, printing and dyeing industry, electroplating industry, pesticide industry and pharmaceutical production. The vapor of this compound is highly irritating to human mucous membranes and skin, and can cause conjunctivitis, bronchitis, pneumonia, pulmonary edema, and contact dermatitis. Direct contact of the skin and eyes with its liquid can cause burns, and severe liver and kidney damage; Moreover, this compound can also cause occupational asthma and c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/26C09K11/06B01J20/22B01J20/30G01N21/64
CPCC07D215/26C09K11/06B01J20/22G01N21/643G01N21/6447C09K2211/1029C09K2211/1011
Inventor 林奇贾钰魏太保张有明姚虹
Owner NORTHWEST NORMAL UNIVERSITY
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