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Preparation of hydrazone chiral covalent organic framework material and application of hydrazone chiral covalent organic framework material in metal ion recognition

A technology of covalent organic framework and chirality, which is applied in the direction of material analysis, luminescent materials, and analytical materials through optical means, and achieves good application prospects, high stability, and good crystallinity

Active Publication Date: 2021-01-05
SOUTH CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the research on COF-based QCM sensors for metal ion recognition has not been reported

Method used

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  • Preparation of hydrazone chiral covalent organic framework material and application of hydrazone chiral covalent organic framework material in metal ion recognition
  • Preparation of hydrazone chiral covalent organic framework material and application of hydrazone chiral covalent organic framework material in metal ion recognition
  • Preparation of hydrazone chiral covalent organic framework material and application of hydrazone chiral covalent organic framework material in metal ion recognition

Examples

Experimental program
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Effect test

Embodiment 1

[0039] Example 1 A preparation method of hydrazone chiral covalent organic framework material

[0040] The preparation method comprises the following steps:

[0041] (1) Tris(4-formylphenyl)amine (Tfpa, 6.6mg, 0.02mmol), chiral hydrazide monomer (S)-2,5-bis(2-methylbutoxy) p-phenylene The mixture of dicarboxylic acid dihydrazide (Mth, 11.0mg, 0.03mmol) and 1.0mL of mesitylene solution was put into a 10mL pressure-resistant reaction flask, mixed thoroughly and then added with 0.1mL of 6M acetic acid solution.

[0042] (2) Bubble the pressure-resistant reaction vial with argon gas for 10 minutes, then quickly seal it, and then place the pressure-resistant reaction vial in an oven at 120° C. to react for three days.

[0043] (3) Cool to room temperature after the reaction, collect the precipitate by suction filtration, wash the precipitate with 1,4-dioxane, tetrahydrofuran and absolute ethanol several times in sequence, and finally put it in a vacuum drying oven for 24 hours at ...

Embodiment 2

[0044] The preparation method of embodiment 2COF-based QCM wafer

[0045] The preparation method comprises the following steps:

[0046](1) Soak the QCM chip in piranha solution (98% H 2 SO 4 :30%H 2 o 2 =7:3) for 10min, then rinse with a large amount of deionized water, dry with nitrogen, then soak the cleaned QCM chip in β-mercaptoethylamine solution for 12h, then rinse with deionized water, and dry with nitrogen to obtain Amino-modified QCM chips are ready for use.

[0047] (2) First put tris(4-formylphenyl)amine (Tfpa, 6.6mg, 0.02mmol) and mesitylene (8mL) into the reaction bottle for ultrasonic dissolution, and then put the above-mentioned amino-modified QCM chip face down Fix it on a polytetrafluoroethylene bracket and put it into the reaction bottle, then add the chiral hydrazide monomer (S)-2,5-bis(2-methylbutoxy)terephthalic acid dihydrazide (Mth , 11.0mg, 0.03mmol) and 0.2mL 6M acetic acid solution, the resulting mixture was bubbled with argon, then the reactio...

experiment example 1

[0048] Experimental Example 1 Performance Determination of Hydrazone Chiral Covalent Organic Framework Materials

[0049] The hydrazone chiral covalent organic framework material prepared in Example 1 was used as the material, and its performance was measured.

[0050] (1) X-ray powder diffraction measurement

[0051] The powder X-ray diffraction spectrum of the chiral covalent organic framework material prepared in Example 1 was measured on a Science Ultima IV X-ray powder diffractometer in Japan, using CuKα radiation, at a 2θ range of 2°-40°, at room temperature. Such as figure 2 As shown, 5.5° and 9.0° in the figure are the characteristic diffraction peaks of chiral covalent organic framework materials, indicating that it has better crystallinity.

[0052] (2) Measurement of Fourier transform infrared spectroscopy

[0053] The chiral covalent organic framework material prepared in Example 1 was measured by Fourier Transform Infrared Spectroscopy (FT-IR). The determinati...

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Abstract

The invention belongs to the technical field of covalent organic framework functional materials, particularly relates to preparation of a hydrazone chiral covalent organic framework material and an application of the hydrazone chiral covalent organic framework material in metal ion recognition, and aims to develop a novel sensing material which has strong fluorescence and can be used as a fluorescent probe for the metal ion recognition. The hydrazone chiral covalent organic framework material is obtained through an acetic acid catalytic reaction of tris (4-formyl phenyl)amine and chiral hydrazide monomers in an organic solvent under the protection action of inert gas, and the prepared hydrazone chiral covalent organic framework material has the advantages of being good in crystallinity, high in stability and the like, has strong fluorescence and can be used as a fluorescent probe for recognizing Fe (III) ions. Meanwhile, the hydrazone chiral covalent organic framework material is bonded to an amino-modified QCM wafer through an in-situ growth method, and a COF-based QCM sensor capable of achieving high-selectivity recognition of Fe (III) is prepared.

Description

technical field [0001] The invention belongs to the technical field of covalent organic framework functional materials, and in particular relates to the preparation of a hydrazone chiral covalent organic framework material and its application in metal ion recognition. Background technique [0002] Covalent organic frameworks (COFs) are a new class of ordered porous crystalline materials composed of organic building units linked by strong covalent bonds. As one of the typical representatives of new porous materials, COFs have attracted extensive attention because of their light weight, low density, adjustable frame size, pore modification, large surface area, and good thermal and chemical stability. In recent years, COFs with responsive fluorescence properties have been considered as a potential chemical sensing material. COFs containing special functional groups can provide multiple identical binding sites within the extended framework. When one of the sites is bound, the s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G83/00C09K11/06G01N21/64
CPCC08G83/008C09K11/06G01N21/6428C09K2211/14
Inventor 蔡松亮李殿梅章伟光汤西豪郑盛润
Owner SOUTH CHINA NORMAL UNIVERSITY
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