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C-C single bond connected water-soluble cation covalent organic framework and preparation method thereof

A water-soluble cationic, covalent organic framework technology, applied in the field of material science, can solve the problems of poor water solubility, long time consumption, affecting the processing of COFs materials, etc., to achieve the effect of convenient water solubility, avoidance of dehydration process, and good water solubility

Active Publication Date: 2022-07-22
SHANGHAI UNIV OF ENG SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The interlayer electrostatic repulsion of ionic COFs can improve the water solubility of COFs. It has been reported that ultrasonic treatment can realize the dispersion of ionic COFs. However, if the water solubility of COFs itself is poor, COFs will still aggregate and precipitate after standing, which will affect the processing of COFs materials.
Another result of the methyl group at the ortho or para position of the electron-withdrawing group is that the dehydration process occurs to form a stable conjugated structure, and COFs linked by C-C single bonds are also urgently needed in synthetic chemistry; Yuan et al. (Yuan, C .; Fu, S.; Yang, K.; Hou, B.; Liu, Y.; Jiang, J.; Cui, Y. Crystalline C-Cand C=C bond-linked chiral covalent organic frameworks.J.Am. Chem.Soc.2021, 143(1), 369-381) firstly synthesize COFs linked by C=C double bonds, and then use sodium borohydride to reduce the double bonds to prepare COFs linked by C-C single bonds, but the preparation process is expensive It takes a long time, and the prepared C-C single-bonded COFs are non-ionic COFs and have poor water solubility

Method used

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  • C-C single bond connected water-soluble cation covalent organic framework and preparation method thereof
  • C-C single bond connected water-soluble cation covalent organic framework and preparation method thereof
  • C-C single bond connected water-soluble cation covalent organic framework and preparation method thereof

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preparation example Construction

[0046] The present invention provides a preparation method of the above-mentioned C-C single bond connecting water-soluble cationic covalent organic skeleton, comprising the following steps:

[0047] (1) trimesicaldehyde is dissolved in organic solvent to obtain trimesicaldehyde solution;

[0048] (2) dichloromethyl viologen and alkali are dissolved in alcohol to obtain mixed solution;

[0049] (3) adding the mixed solution obtained in step (2) into the trimesicaldehyde solution obtained in step (1) to obtain a reaction mixture;

[0050] (4) reacting the reaction mixture obtained in step (3) under nitrogen protection, and post-processing to obtain a C-C single bond connecting water-soluble cationic covalent organic framework precursor;

[0051] (5) continuing the reaction with the C-C single bond-connected water-soluble cationic covalent organic framework precursor obtained in step (4), and post-processing to obtain the C-C single-bond-connected water-soluble cationic covalen...

Embodiment 1

[0065] In this example, a new type of aldol condensation reaction is verified by reacting dichloromethyl viologen with benzaldehyde to generate a model compound.

[0066] reaction process such as figure 1 shown, the specific steps are as follows:

[0067] (1) 128.5 mg of dichloromethyl viologen, 2 mL of benzaldehyde and 100 μL of sodium hydroxide solution of 10 mmol of methanol were added to 10 mL of methanol, refluxed for 4 days at 90° C., and cooled to room temperature. Washing with 1,4-dioxane gave the brown model compound in 67.7% yield.

[0068] (2) The model compound solution was dehydrated (D 2 O), under 101MHz NMR, the model compound was obtained 13 C spectrum. like figure 2 As shown, the assignment results indicate that the monomers are connected by [-CH 2 -CH(OH)-], that is, the aldol condensation reaction between methyl viologen and benzaldehyde does not take place in the dehydration step.

Embodiment 2

[0070] In this embodiment, C-C single bond water-soluble cation COF is generated by aldol condensation reaction of dichloromethyl viologen and trimesicaldehyde.

[0071] reaction process such as image 3 shown, the specific steps are as follows:

[0072] (1) 33mg of trimesicaldehyde was dissolved in 4mL of 1,4-dioxane, added to a 10mL thick-walled pressure tube to obtain a trimesicaldehyde solution;

[0073] (2) 78 mg of dichloromethyl viologen and 80 mg of sodium hydroxide were dissolved in 4 mL of methanol to obtain a mixed solution;

[0074] (3) the mixed solution obtained in step (2) is added to the trimesicaldehyde solution obtained in step (1) to obtain a reaction mixture;

[0075] (4) heating the reaction mixture obtained in step (3) to 90° C. under nitrogen protection, stirring for 12 hours to form a brown precipitate, then degassing three times using the freeze-pump-thaw technique and vacuum sealing to obtain a C-C single bond connection Water-soluble cationic cova...

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Abstract

The invention relates to the technical field of material science, in particular to a C-C single bond connected water-soluble cation covalent organic framework and a preparation method thereof. The preparation method comprises the following steps: firstly, dissolving benzenetricarboxaldehyde in an organic solvent to obtain a benzenetricarboxaldehyde solution; the preparation method comprises the following steps: dissolving dichloromethyl viologen and alkali in alcohol to obtain a mixed solution; then adding the mixed solution into a benzenetricarboxaldehyde solution, reacting under the protection of nitrogen, and performing post-treatment to obtain a C-C single bond connected water-soluble cation covalent organic framework precursor; continuing to react, and performing post-treatment to obtain the C-C single bond connected water-soluble cation covalent organic framework. The obtained C-C single bond connected water-soluble cation covalent organic framework has cation characteristics and good water solubility, the cation characteristics of the C-C single bond connected water-soluble cation covalent organic framework facilitate integration of trifluoromethanesulfonimide, integration of lithium ions is achieved, and high lithium ion conductivity is obtained; and meanwhile, good water solubility facilitates preparation and processing of the lithium ion electrode.

Description

technical field [0001] The invention relates to the technical field of material science, in particular to a C-C single bond connecting water-soluble cationic covalent organic framework and a preparation method thereof. Background technique [0002] Covalent organic frameworks (COFs) are porous materials formed by covalent bonding of organic monomers. COFs formed by reversible covalent bonds have poor stability, and the development of the preparation of COFs linked by irreversible covalent bonds has attracted wide interest (Haase, F.; Lotsch, B.V. Solving the COF trilemma: towards crystalline, stable and functional covalent organic frameworks. Chem.Soc.Rev .2020, 49(23), 8469-8500). Meanwhile, as all-organic materials, COFs tend to exhibit poor water solubility (Mal, A.; Vijayakumar, S.; Mishra, R.K.; Jacob, J.; Pillai, R.S.; Dileep Kumar, B.S.; Ajayaghosh, A. Supramolecular Surface charge regulation in ionic covalent organic nanosheets: reversible exfoliation and controlle...

Claims

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Application Information

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IPC IPC(8): C08G12/26
CPCC08G12/26
Inventor 尹学博冯雪楠
Owner SHANGHAI UNIV OF ENG SCI
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