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Covalent organic framework material containing beta-ketoenamine structure, and preparation method and application thereof

A technology of covalent organic framework and β-ketoenamine, which is applied in the field of covalent organic framework materials and their preparation, can solve the problems of difficult to meet the actual needs of electrochemical energy storage devices, low specific capacitance value of COFs materials, etc., and achieve excellent thermal performance. Stability and chemical stability, excellent rate performance and cycling stability, the effect of enriched porosity

Active Publication Date: 2019-09-13
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, there are still very few COFs materials currently used in the field of electrochemical energy storage, and the specific capacitance of COFs materials reported publicly is still low, which is difficult to meet the actual needs of electrochemical energy storage devices.

Method used

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  • Covalent organic framework material containing beta-ketoenamine structure, and preparation method and application thereof
  • Covalent organic framework material containing beta-ketoenamine structure, and preparation method and application thereof
  • Covalent organic framework material containing beta-ketoenamine structure, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] (1) Preparation of monomer 4,4'-(pyrene-1,6-disubstituted)diphenylamine:

[0029] Under nitrogen protection, 1,6-dibromopyrene (1.80g, 5.0mmol), 4-aminophenylboronic acid pinacol ester (3.28g, 15.0mmol), tetrabutylammonium bromide ( TBAB) (0.51g, 10wt%), catalyst tetrakistriphenylphosphine palladium (Pd(PPh 3 ) 4 ), adding the solvent K after bubbling deoxygenation 2 CO 3 (aq., 2M) 30mL, 1,4-dioxane 90mL, temperature-controlled reflux reaction for 72 hours. After the reaction, the crude product was purified by column chromatography with 100-200 mesh basic alumina as the stationary phase and petroleum ether / ethyl acetate (volume ratio 1:2) as the eluent to obtain 1.48 g of off-white powder with a yield of 77%.

[0030] (2) Preparation of covalent organic framework materials:

[0031] Weigh the monomer 4,4'-(pyrene-1,6-disubstituted)diphenylamine (57.6mg, 0.15mmol) synthesized in step (1), and 2,4,6-triformylpyroglucinol (TFP ) (21.0mg, 0.10mmol) into a Pyrex tube r...

Embodiment 2

[0033] The synthesis steps of the monomer 4,4'-(pyrene-1,6-disubstituted)diphenylamine are the same as the step (1) in Example 1, and the 4,4'-(pyrene-1,6-disubstituted) Put 57.6mg of diphenylamine and 21.0mg of 2,4,6-triformylpyroglucinol (TFP) into a high temperature and high pressure resistant Pyrex tube, add 2mL of o-dichlorobenzene and 1mL of n-butanol, and sonicate for 2min to form a uniform dispersion Then add 0.3mL of 6M acetic acid aqueous solution as an acidic catalyst, seal the Pyrex tube and put it into a liquid nitrogen bath for quick freezing, then evacuate until the pressure inside the tube reaches 0.15mmHg, and then thaw to remove the air in the solvent; Quick freezing-vacuumizing-thawing operation cycles more than 3 times; finally, the reaction tube was heated to 120°C and left to react for 5 days. After the reaction, the solid obtained by suction filtration was extracted by Soxhlet with anhydrous tetrahydrofuran for more than 24 hours, and finally the solid w...

Embodiment 3

[0035] The synthesis steps of monomer 4,4'-(pyrene-1,6-disubstituted)diphenylamine are the same as step (1) in Example 1, and 4,4'-(pyrene-1,6-disubstituted)diphenylamine is weighed Put 57.6mg of aniline and 21.0mg of 2,4,6-triformylpyroglucinol (TFP) into a Pyrex tube resistant to high temperature and high pressure, add 1mL of o-dichlorobenzene and 2mL of n-butanol, and sonicate for 2min to form a uniform dispersion , then add 0.3mL of 6M acetic acid aqueous solution as an acidic catalyst, seal the Pyrex tube and put it into a liquid nitrogen bath for quick freezing, then evacuate until the pressure in the tube reaches 0.15mmHg, and then thaw to remove the air in the solvent; quick freeze the liquid nitrogen bath - Vacuum pumping - thawing operation cycle for more than 3 times; finally, heat the reaction tube to 120°C and let it stand for reaction for 5 days. After the reaction, the solid obtained by suction filtration was extracted by Soxhlet with anhydrous tetrahydrofuran f...

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Abstract

The invention discloses a covalent organic framework material containing a beta-ketoenamine structure, and a preparation method and an application thereof. The covalent organic framework material hasa pyrene structural unit and the beta-ketoenamine structure. The preparation method comprises the following steps: uniformly mixing pyrenyl diphenylamine and 2,4,6-triformyl pyrogallol in an organic solvent, adding a weakly-acidic catalyst, and carrying out a reversible Schiff base reaction and an irreversible enol-ketone tautomerization reaction under solvothermal conditions so as to obtain the covalent organic framework material containing the beta-ketoenamine structure, wherein the beta-ketoenamine structure comprises a repeated unit as shown in a formula I or a formula II which are described in the specification. The covalent organic framework material provided by the invention has the advantages of high crystallinity, porosity, regular and ordered pore channel structure, high specificsurface area, low density, good thermal stability and chemical stability, and good application prospects in the fields of gas storage and separation, catalysis, sensing, energy storage and conversion, drug delivery and the like. In the formula I and the formula II, R is one selected from the group consisting of hydrogen and C1-C20 straight-chain or branched-chain alkyl or alkoxy groups.

Description

technical field [0001] The invention belongs to the technical field of organic functional materials, in particular to a covalent organic framework material containing a β-ketoenamine structure and its preparation method and application. Background technique [0002] Covalent organic frameworks (COFs) are a new class of crystalline porous polymers emerging in the last ten years, and are a research hotspot in the field of polymer science. The biggest feature of this kind of material is its rich porosity, regular and ordered pore structure, low skeleton density, and high specific surface area. It has been widely used in the fields of gas storage and separation, catalysis, and sensing. In contrast, although the application of COFs in the field of energy storage and conversion has a good application prospect, there are still few researches at present. The main reason is that the electrochemical stability of the material is insufficient and the specific capacitance value is low. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G83/00
CPCC08G83/008
Inventor 赖文勇刘园园王倩张林李晓鹏李祥春黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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