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Hydrazone chiral covalent organic framework material containing hydroxyl as well as preparation method and application of hydrazone chiral covalent organic framework material

A covalent organic framework and chiral technology, applied in separation methods, chemical instruments and methods, and other chemical processes, can solve problems such as difficulty in maintaining crystallinity, low symmetry, and achirality, and achieve good crystallinity, The effect of high thermal stability and easy operation

Active Publication Date: 2018-12-21
SOUTH CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although different types of covalent organic frameworks have been successfully synthesized, including boronate-linked, imine-linked, hydrazone-linked, and triazine-linked, etc., the reported covalent organic frameworks are mostly Some are achiral, in contrast, there are few research reports on chiral covalent organic framework materials
To some extent, the design and synthesis of chiral covalent organic framework materials is still a challenging research topic, because achiral covalent organic framework materials with highly Relatively easy to crystallize, while chiral covalent organic framework materials with lower symmetry often have difficulty maintaining good crystallinity during synthesis

Method used

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  • Hydrazone chiral covalent organic framework material containing hydroxyl as well as preparation method and application of hydrazone chiral covalent organic framework material
  • Hydrazone chiral covalent organic framework material containing hydroxyl as well as preparation method and application of hydrazone chiral covalent organic framework material
  • Hydrazone chiral covalent organic framework material containing hydroxyl as well as preparation method and application of hydrazone chiral covalent organic framework material

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Embodiment 1

[0044] Hydrazone chiral covalent organic framework materials containing hydroxyl functional groups provided by the present invention are composed of figure 1 The procedure shown was prepared. Specifically, with R Configuration hydrazide chiral precursor as an example, the R The chiral precursor of configuration hydrazide (10.3 mg, 0.03 mmol), tricarbaldehyde (3.2 mg, 0.02 mmol), 0.5 mL of dioxane and 0.5 mL of mesitylene were placed in a pressure-resistant reaction flask and mixed thoroughly After homogenization, 0.1 mL of acetic acid solution (6 M) was added. The resulting mixture was deoxygenated by argon replacement, quickly sealed, and placed in an oven preheated to 110° C. for crystallization reaction for 3 days. After the reaction was completed, it was cooled to room temperature, and the solid was collected by suction filtration, washed with 1,4-dioxane, tetrahydrofuran in sequence, and finally washed with acetone and dried in vacuum to obtain a chiral covalent organi...

Embodiment 2

[0064] Will R Configuration Hydrazide chiral precursor (20.5 mg, 0.06 mmol), trimesaldehyde (6.5 mg, 0.04 mmol), 0.5 mL of dioxane and 0.5 mL of mesitylene were placed in a pressure-resistant reaction flask and mixed thoroughly After homogenization, 0.1 mL of acetic acid solution (6 M) was added. The resulting mixture was deoxygenated by argon replacement, quickly sealed, and placed in an oven preheated to 110° C. for crystallization reaction for 3 days. Cool to room temperature after the reaction, collect the solid by suction filtration, rinse with 1,4-dioxane, tetrahydrofuran in sequence, and finally rinse with acetone and dry in vacuum to obtain a chiral covalent organic framework material.

Embodiment 3

[0066] Will R Conformational hydrazide chiral precursor (10.3 mg, 0.03 mmol), tricarbaldehyde (3.2 mg, 0.02 mmol), 0.5mL N , N’ - Dimethylformamide and 0.5 mL of mesitylene were placed in a pressure-resistant reaction flask, mixed well, and then 0.1 mL of acetic acid solution (3 M) was added. The resulting mixture was deoxygenated by argon replacement, quickly sealed, and placed in an oven preheated to 120° C. for crystallization reaction for 4 days. After the reaction, cool to room temperature, collect the solid by suction filtration, wash with tetrahydrofuran for several times, then wash with acetone once, and finally vacuum-dry to obtain the chiral covalent organic framework material.

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Abstract

The invention discloses a hydrazone chiral covalent organic framework material containing hydroxyl and a preparation method of the hydrazone chiral covalent organic framework material. The hydrazone bonding chiral covalent organic framework material containing hydroxyl shows the advantages of good crystallinity, high thermal stability, large specific surface area and uniform pore size distribution, as well as good application prospect in the fields of chiral separation and recognition and the like. In addition, the electron circular dichroism test shows that two chiral covalent organic framework materials prepared by hydrazide chiral precursors with R and S configurations are enantiomers respectively. The invention also provides a method for preparing the hydrazone chiral covalent organicframework material containing hydroxyls; the method has the advantages of simple operation, greenness and environment friendliness, good batch reproducibility and suitability for mass production.

Description

technical field [0001] The invention relates to the field of covalent organic framework functional materials, in particular to a hydrazone chiral covalent organic framework material containing a hydroxyl function and its preparation method and application. Background technique [0002] Covalent organic framework (COF) is an emerging molecular sieve-like material, which is composed of small organic molecules containing light elements (C, H, N, O, B, etc.) A crystalline porous polymer with a network structure. This kind of crystalline porous material has many advantages such as light weight, low density, regular structure, high specific surface area, adjustable skeleton size and pore modification, etc. Optoelectronic materials and other fields have potential application value. [0003] In recent years, chiral covalent organic frameworks have attracted great attention of chemists because of their promising application prospects in asymmetric catalysis and separation of chiral...

Claims

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Application Information

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IPC IPC(8): C08G83/00B01J20/29B01J20/30B01D15/38
CPCB01D15/3833B01J20/29C08G83/008
Inventor 蔡松亮陈桂张凯章伟光郑盛润范军
Owner SOUTH CHINA NORMAL UNIVERSITY
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