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A kind of compound, covalent organic framework material and its preparation method and application

A covalent organic framework and compound technology, which is applied in the preparation of carbon-based compounds, organic compounds, alkali metal compounds, etc., can solve the problems of cumbersome preparation methods, poor chemical stability and thermal stability of materials, and achieve simple preparation methods, Effect of high chemical stability and thermal stability

Active Publication Date: 2022-06-24
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, post-functionalization of imine-linked COFs remains challenging, mainly because of the involvement of aldehydes and amines in the polymerization reaction.
[0004] However, the inventors found that the existing covalent organic framework materials often have disadvantages such as relatively cumbersome preparation methods, poor chemical stability and thermal stability of the materials.

Method used

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  • A kind of compound, covalent organic framework material and its preparation method and application
  • A kind of compound, covalent organic framework material and its preparation method and application
  • A kind of compound, covalent organic framework material and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1 Synthesis of compound 5-(2-propynyloxy)isophthalaldehyde:

[0049] (1) 5-hydroxyisophthalaldehyde (0.81g, 5.4mmol), potassium carbonate (0.75g, 5.4mmol) and anhydrous tetrahydrofuran (120ml) were added, heated to reflux for 30 minutes and then added 3-bromopropyne (2.5 ml), the reaction was refluxed for 3 days. Cool to room temperature and filter. After distillation under reduced pressure, it was purified by column chromatography (petroleum ether / ethyl acetate=4 / 1, volume ratio) to obtain 0.82 g of white flocculent 5-(2-propynyloxy)isophthalaldehyde aniline, which produced Rate: 81%. 1 H NMR (d 6 -DMSO,400MHz):δ=3.67(t,1H),5.02(d,2H),7.81(d,2H),8.09(s,1H),10.08(s,2H)ppm. 13 C-NMR (d 6 -DMSO, 400MHz): 56.42, 78.72, 79.41, 120.75, 124.05, 138.58, 158.55, 192.62. Its H NMR and C NMR spectra are as follows figure 1 and figure 2 shown.

[0050] The reaction is as follows:

[0051]

Embodiment 2

[0053] To a 10 ml tube was added 5-(2-propynyloxy)isophthalaldehyde (11.3 mg, 0.06 mol) and 1,3,5-tris-(4-aminophenyl)benzene (14.1 mg, 0.04 mmol) Ethanol (1 ml) was added to obtain a pale yellow precipitate, 0.2 ml of acetic acid solution was added to the above mixed solution, and the tube was sealed. Three freeze-thaw cycles were performed and heated in a 120°C oil bath for 3 days. The reaction was completed, centrifuged to obtain a light yellow precipitate, the precipitate was washed three times with tetrahydrofuran, and then fully washed with a Soxhlet extractor (acetone, tetrahydrofuran), and vacuum-dried at 120 degrees Celsius for 12 hours to obtain 11 mg based on 5-(2-propynyloxy) Covalent organic framework materials of isophthalaldehyde building blocks (denoted as BPPA-COF, where Represents repeating units), and the infrared spectrum of covalent organic framework material BPPA-COF is shown in Figure 4 As described, the SEM image is as Figure 5 As shown, the TEM i...

Embodiment 3

[0056] Example 3 Stability Experiment

[0057] The BPPA-COF in Example 2 was soaked in an organic solution of N,N-dimethylformamide, methanol, ethanol, acetone, and tetrahydrofuran for three days, and then dried by centrifugation, and then the infrared absorption spectrum was measured, as shown in the figure. The position of each functional group peak has not changed, which is consistent with the initial one. From the thermogravimetric analysis curve in the figure, it can be seen that the BPPA-COF will have significant weight loss at 300 °C, indicating that the thermal stability is good.

[0058] The covalent organic framework material prepared in Example 2 is used for modification, and the thiophenol group containing azide is connected through the click reaction (as shown in the figure below). The experiment shows that it can adsorb mercury ions in water.

[0059]

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Abstract

The invention discloses a compound, a covalent organic framework material and its preparation method and application. The compound has a structure shown in formula (I): the compound can be used as a starting material or an intermediate for the preparation of compounds including formula (II) Covalent organic framework material with the structure shown as the basic unit: the covalent organic framework material is a covalent organic framework formed by Schiff base reaction, with uniform pore size, regular structure, and good chemical and thermal stability .

Description

technical field [0001] The invention belongs to the technical field of organic functional materials, and relates to a compound, a covalent organic framework material and a preparation method and application thereof. Background technique [0002] The information disclosed in this Background section is only for enhancement of understanding of the general background of the invention and should not necessarily be taken as an acknowledgement or any form of suggestion that this information forms the prior art already known to a person of ordinary skill in the art. [0003] In recent years, COF materials have attracted much attention due to their potential applications in selective separation, gas storage, catalysis, sensors, etc. As the most interesting COF materials, imine-linked COFs are prepared by Schiff base reactions. To extend its specific applications, functionalization of imine-linked COFs is a simple strategy that can provide a structurally and chemically precise platfo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C47/575C07C45/64B01J31/06B01J32/00C09K11/06C08G83/00B01J20/26B01J20/28B01J20/30C02F1/28C02F101/20
CPCC07C47/575C07C45/64B01J31/063C09K11/06C08G83/008B01J20/262B01J20/28011C02F1/285C09K2211/1425C09K2211/1433C09K2211/1475C02F2101/20
Inventor 董育斌李梦琪元宁宁
Owner SHANDONG NORMAL UNIV
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