Preparation of amino-functionalized hydrazone covalent organic framework material and application thereof

A covalent organic framework, amino functionalization technology, applied in the analysis of materials, material excitation analysis, material analysis by optical means, etc., can solve the problems of reducing the crystallinity of COF, complex synthesis steps, long reaction time, etc., to achieve crystallization The effect of good degree, high stability and rich amino functional sites

Pending Publication Date: 2021-08-13
SOUTH CHINA NORMAL UNIVERSITY
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  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The first strategy is to synthesize nitro-functionalized COF first, and then use post-modification method to reduce it to amino-functionalized COF material, but the synthesis steps of this strategy are complicated, and the crystallinity of the modified COF is also difficult to maintain.
The second strategy is to use the monomer exchange method to prepare amino-functionalized COFs. However, this strategy not only has complex synthesis steps and long reaction time, but also reduces the crystallinity of COF after monomer exchange.
However, since the four amino groups of the tetraamine monomer have the same reactivity, the formation of the target COF will also be accompanied by the formation of other by-products

Method used

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  • Preparation of amino-functionalized hydrazone covalent organic framework material and application thereof
  • Preparation of amino-functionalized hydrazone covalent organic framework material and application thereof
  • Preparation of amino-functionalized hydrazone covalent organic framework material and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1 The specific synthesis method of amino functionalized dihydrazide monomer (Ath) is:

[0038] according to figure 1The synthetic route of the amino-functionalized dihydrazide monomer shown, weighed 209 mg of dimethyl 2-aminoterephthalate (Dth) into a 10 mL microwave reaction tube, added 2 mL of absolute ethanol, and added 900 μL of 98 % of hydrazine hydrate. After mixing well, use the liquid nitrogen freezing deoxygenation method to remove oxygen for 15 minutes, and then place it in an oil bath at 80°C for 24 hours. After cooling to room temperature, it was filtered, the solid was washed with absolute ethanol, and then dried in a vacuum oven at 100°C overnight to finally obtain the yellow-green solid product Ath, namely 2-aminoterephthalic acid dihydrazide. 1 H NMR (600MHz, DMSO-d 6 ): δ (ppm) = 9.65 (s, 1H), 9.57 (s, 1H), 7.44 (d, J = 8.2Hz, 1H), 7.15 (d, J = 1.7Hz, 1H), 6.88 (dd, J =8.2,1.7Hz,1H),6.46(s,2H),4.44(s,4H); 13 C NMR (150MHz, DMSO-d 6 ), δ...

Embodiment 2

[0039] Example 2 Preparation method of amino functionalized hydrazone covalent organic framework material

[0040] The preparation method of amino functionalized hydrazone covalent organic framework material is as follows figure 2 As shown in the synthetic route map, specifically include the following steps:

[0041] (1) A mixed solvent of trimesaldehyde (Bta, 6.4mg, 0.04mmol), amino-functionalized dihydrazide monomer (Ath, 12.6mg, 0.06mmol) and 1.0mL o-dichlorobenzene / n-butanol ( The volume ratio of o-dichlorobenzene and n-butanol (1:1) was placed in a 10mL pressure-resistant reaction flask, and after mixing well, 0.1mL of 6M acetic acid solution was added.

[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 110° C. for three days.

[0043] (3) Cool to room temperature after the reaction, collect the precipitate by suction filtration, wash the precipi...

experiment example 1

[0044] Experimental example 1 Determination of properties of amino functionalized hydrazone covalent organic framework materials

[0045] The amino-functionalized hydrazone covalent organic framework material prepared in Example 2 was used as the material, and its performance was measured.

[0046] (1) X-ray powder diffraction measurement

[0047] On the Science Ultima IV X-ray powder diffractometer in Japan, Cu Kα radiation was used to measure the powder X of amino-functionalized hydrazone covalent organic framework materials under 40mA and 30kV at room temperature in the 2θ range of 2°-40°. Ray Diffraction Spectrum. Such as image 3 As shown, 3.5°, 7.0° and 9.4° in the figure are the characteristic diffraction peaks of the amino-functionalized hydrazone covalent organic framework material, indicating that it has good crystallinity.

[0048] (2) Fourier transform infrared spectroscopy (FT-IR) measurement

[0049] A Spectrum Two FT-IR spectrometer from PerkinElmer, Germany...

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Abstract

The invention belongs to the technical field of covalent organic framework functional materials, particularly relates to preparation and application of an amino-functionalized hydrazone covalent organic framework material, and aims to develop a novel amino-functionalized sensing material which has a strong fluorescence effect and can be used as a fluorescent probe for metal ion recognition. The preparation method comprises the following steps: firstly designing and synthesizing an amino-functionalized dihydrazide monomer containing functional groups with different reaction activities, and then carrying out acetic acid catalytic reaction on the amino-functionalized dihydrazide monomer and a benzenetricarboxaldehyde monomer in an organic solvent under the protection effect of inert gas. The prepared amino-functionalized hydrazone covalent organic framework material has the advantages of rich amino functional sites, good crystallinity, high stability and the like, has strong fluorescence, and can be used as a fluorescent probe for high-sensitivity and high-selectivity recognition of Fe (III) ions.

Description

technical field [0001] The invention belongs to the technical field of covalent organic framework functional materials, and specifically relates to the preparation and application of an amino functionalized hydrazone covalent organic framework material. 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 chemical sensing material with great application potential. Iron ions are one of the metal ions that play an important role in humans and other organisms, and have a significant impact on biochemical process...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G12/04G01N21/64
CPCC08G12/04G01N21/6402
Inventor 蔡松亮张舒媛李舒晴章伟光汤西豪弯佳怡
Owner SOUTH CHINA NORMAL UNIVERSITY
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