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Acid gas molecular responsive covalent organic material, preparation method and application thereof

An acid gas and covalent organic technology, which is applied in the analysis of materials, material analysis by optical means, color/spectral characteristic measurement, etc., to achieve the effects of mild system, simple preparation process and convenient post-processing

Inactive Publication Date: 2020-06-26
FUZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, it is still challenging to design and synthesize covalent organic framework material sensors with high sensitivity to acid vapor molecules, easy operation, fast response, and obvious naked-eye coloration.

Method used

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  • Acid gas molecular responsive covalent organic material, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1. Synthesis of covalent organic framework material DS-DBAN

[0023] Combine 100 mg 4,4',4'',4'''-[1,2,4,5-phenyltetrakis(methyleneoxy)]tetra[benzaldehyde] with 71 mg of p-phenylenediamine Add a 250 mL three-necked round bottom flask, and then add 170 mL of anhydrous acetonitrile solution, mix well, add 0.02 mL 6M acetic acid, and react at 95°C for 6 h; after the reaction is over, filter the reaction solution and use two filter cakes. After washing with methyl chloride and ethanol for 3 times, the washed solid was vacuum dried at 60°C for 24 h to obtain the product DS-DBAN with a yield of 50.7%. Solid carbon nuclear magnetic resonance ( 13 C solid state NMR) shows that the characteristic functional group -C=N- of the covalent organic framework material DS-DBAN has an absorption peak at 159 ppm; the infrared (FT-IR) spectrum results show at 1624 cm -1 There is a characteristic absorption peak of -C=N-.

Embodiment 2

[0024] Example 2. Synthesis of covalent organic framework material DS-JBAN

[0025] Combine 100 mg 4,4',4'',4'''-[1,2,4,5-benzenetetrayltetra(methyleneoxy)]tetra[benzaldehyde] with 71 mg m-phenylenediamine Put it into a 250 mL three-necked round bottom flask, then add 170 mL of anhydrous acetonitrile solution, mix well, add 0.02 mL 6M acetic acid, and react at 95°C for 10 h; after the reaction is over, filter the reaction solution and use the filter cake Dichloromethane and ethanol were washed 3 times, and the washed solid was vacuum dried at 60°C for 24 h to obtain the product DS-JBAN with a yield of 56.1%. Solid carbon nuclear magnetic resonance ( 13 C solid state NMR) shows that the characteristic functional group -C=N- of the covalent organic framework material DS-JBAN has an absorption peak at 158 ​​ppm; the infrared (FT-IR) spectrum result shows at 1624 cm -1 There is a characteristic absorption peak of -C=N-.

Embodiment 3

[0026] Example 3. Synthesis of covalent organic framework material DS-LBAN

[0027] Combine 100 mg 4,4',4'',4'''-[1,2,4,5-benzenetetrayltetra(methyleneoxy)]tetra[benzaldehyde] with 71 mg o-phenylenediamine Put it into a 250 mL three-necked round bottom flask, and then add 170 mL of anhydrous acetonitrile solution, mix well, add 0.02 mL 6M acetic acid, and react at 95 ℃ for 8 h; after the reaction is over, filter the reaction solution and use the filter cake Dichloromethane and ethanol were washed three times, and the washed solid was vacuum dried at 60°C for 24 h to obtain the product DS-LBAN with a yield of 37.5%. Solid carbon nuclear magnetic resonance ( 13 C solid state NMR) shows that the characteristic functional group -C=N- of the covalent organic framework material DS-LBAN has an absorption peak at 159 ppm; the infrared (FT-IR) spectrum results show at 1624 cm -1 There is a characteristic absorption peak of -C=N-.

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Abstract

The invention discloses an acid gas molecular responsive covalent organic material, a preparation method and application thereof. The preparation method comprises the following steps: subjecting a tetradentate aldehyde compound 4, 4', 4'', 4'''-[1, 2, 4, 5-benzenetetrayl tetrakis(methyleneoxy)]tetrakis[benzaldehyde] or 4-{2, 2-bis[(4-formylphenoxy)methyl]-3-(4-formylphenoxy)propoxy}benzaldehyde and a bidentate amine compound 4, 4'-diaminodiphenylmethane or m-phenylenediamine or p-phenylenediamine or o-phenylenediamine or trans-1, 4-cyclohexanediamine to Schiff base amine aldehyde condensationreaction for assembly to obtain the covalent organic framework material. The obtained covalent organic framework material has an obvious naked eye colorimetric phenomenon on volatile acid vapor molecules, the response time is short and the operation is simple.

Description

Technical field [0001] The invention belongs to the field of organic material preparation, and specifically relates to a covalent organic material responsive to acid gas molecules, and a preparation method and application thereof. Background technique [0002] For a long time, traditional pH detection has focused on the liquid acidic environment, such as oceans, lakes, and industrial wastewater, which have a great impact on human production activities and the environment. Detection methods include pH test paper, acid-base indicator, metal electrode method and glass electrode method. With the refinement of human production activities, the detection of acid vapor molecules in gas atmospheres has attracted more and more attention. [0003] Covalent organic framework materials are a class of organic materials that are connected in order by organic monomers through covalent bonds [Angewandte Chemie International Edition, 2018, 57, 4850-4878]. It is composed of light elements C, H, O ,...

Claims

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Application Information

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IPC IPC(8): C08G83/00G01N21/33G01N21/3563G01N24/08
CPCC08G83/008G01N21/33G01N21/3563G01N24/08G01N2021/3595
Inventor 白正帅李熠王梦美林丽君邓紫琴鲍晓军岳源源袁珮朱海波王廷海
Owner FUZHOU UNIVERSITY
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