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Covalent organic framework material containing oxadiazole connecting element

A technology of covalent organic frameworks and linking groups, applied in organic compound/hydride/coordination complex catalysts, inorganic chemistry, hydrogen production, etc., to achieve the effects of promoting separation and transportation, improving performance, and broadening the absorption range

Active Publication Date: 2022-02-25
HEBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the irreversibility of the reaction of acid chlorides and hydrazides, which usually leads to the formation of amorphous polymers, COFs containing oxadiazole moieties have not yet been reported.

Method used

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  • Covalent organic framework material containing oxadiazole connecting element
  • Covalent organic framework material containing oxadiazole connecting element
  • Covalent organic framework material containing oxadiazole connecting element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] In a Schlenk tube, add 1,3,5-triformylbenzene (32.4 mg, 0.2 mmol), 2,5-diethoxyterephthalic hydrazide (84.9 mg, 0.3 mmol), mesitylene (6 mL ), anhydrous dioxane (2mL) and aqueous acetic acid solution (0.8mL, 6M), the resulting mixture was sonicated for 10 minutes, and then the air in the tube was removed by three cycles of "freezing-vacuum-thawing" with liquid nitrogen, and the The Schlenk tube was sealed, and after heating at 120°C for 3 days, the resulting solid powder was filtered, washed with tetrahydrofuran and acetone several times, and dried in vacuum at 60°C for 12 hours to obtain COFs containing N-acylhydrazone linkers.

[0032] COFs containing N-acylhydrazone linkers (10 mg, 0.05 mmol), copper triflate (18 mg, 0.05 mmol), cesium carbonate (32 mg, 0.1 mmol) and N,N-dimethylformamide ( 15mL) into a dry flask and heated at 120°C for 72 hours. During the reaction, the same amount of copper trifluoromethanesulfonate (that is, both 18mg, 0.05mmol) was added twice (a...

Embodiment 2

[0038] In a Schlenk tube, add 2,4,6-tris(4-formylphenyl)-1,3,5-triazine (80.5 mg, 0.2 mmol), 2,5-diethoxyterephthalamide Hydrazide (84.6mg, 0.3mmol), mesitylene (2.7mL), anhydrous dioxane (1.3mL) and aqueous acetic acid (0.4mL, 6M), the resulting mixture was sonicated for 10 minutes, and then washed with liquid nitrogen "Freeze-vacuum-thaw" cycled three times to remove the air in the tube, sealed the Schlenk tube, heated at 120 °C for 3 days, filtered the resulting solid powder, washed with tetrahydrofuran and acetone several times, and dried in vacuum at 60 °C COFs containing N-acylhydrazone linkers were obtained after 12 hours.

[0039] COFs containing N-acylhydrazone linkers (13 mg, 0.05 mmol), copper triflate (18 mg, 0.05 mmol), cesium carbonate (32 mg, 0.1 mmol) and ultra-dry N,N-dimethylmethane Amide (15mL) was packed into a dry flask and heated at 115°C for 72 hours. During the reaction, the same amount of copper trifluoromethanesulfonate (that is, 18mg, 0.05mmol) was ...

Embodiment 3

[0041] In a Schlenk tube, add 1,3,5-tris(4-formylphenyl)benzene (78.0 mg, 0.2 mmol), trimellitic hydrazide (50.4 mg, 0.2 mmol), mesitylene (20 mL), Anhydrous dioxane (20 mL) and acetic acid aqueous solution (4 mL, 6M), the resulting mixture was sonicated for 10 minutes, and then the air in the tube was removed by "freeze-vacuum-thaw" cycle with liquid nitrogen three times, and the Schlenk tube was sealed , after heating at 120 °C for 3 days, the resulting solid powder was filtered, washed with THF and acetone several times, and dried under vacuum at 60 °C for 12 h to obtain COFs containing N-acylhydrazone linkers.

[0042] COFs containing N-acylhydrazone linkers (9.8 mg, 0.05 mmol), copper triflate (18 mg, 0.05 mmol), potassium carbonate (13.8 mg, 0.1 mmol) and ultra-dry toluene (15 mL) were charged The dried flask was heated at 120°C for 72 hours. During the reaction, the same amount of copper trifluoromethanesulfonate (ie, both 18 mg, 0.05 mmol) was added twice (at an interv...

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Abstract

The invention relates to a covalent organic framework material containing an oxadiazole connecting element. The preparation method of the material comprises the following steps: (1) adding aromatic aldehyde, aromatic formylhydrazine, a first organic solvent and an inorganic acid aqueous solution into a Schlenk tube, and reacting the mixture at 100-130 DEG C for 3-7 days to obtain COFs containing an N-acylhydrazone linking element; (2) adding the COFs, copper salt and carbonate into a second organic solvent, and reacting the components at 90-120 DEG C for 3-7 days to obtain the COFs containing the oxadiazole connecting element. The post-synthesis modification strategy of COFs provided by the invention not only widens the absorption range of COFs in a visible light region, but also can better promote the separation and transportation of photon-generated carriers, thereby improving the performance of photocatalytic water production for hydrogen production.

Description

technical field [0001] The invention belongs to the field of new energy materials, and in particular relates to the preparation of a covalent organic framework material containing an oxadiazole linking unit and its application in visible light catalytic reactions. Background technique [0002] Covalent Organic Frameworks (COFs) are crystalline porous materials with two-dimensional or three-dimensional ordered structures formed by organic structural units connected by covalent bonds. They have large specific surface area, diverse synthesis methods, modular synthesis and It is easy to modify and modify, and has shown good application prospects in the fields of gas adsorption and separation, photoelectricity, catalysis, and energy storage. It is generally believed that the function of COFs comes from its building blocks, while the stability is attributed to the covalent bonds connecting the building blocks. Therefore, based on the basic principles of network chemistry and dyna...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G83/00B01J31/06C01B3/04
CPCC08G83/008B01J31/063C01B3/042C01B2203/1041C01B2203/0277B01J35/39Y02E60/36
Inventor 王瑞虎杨帅龙梁均
Owner HEBEI UNIV OF TECH
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