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Chiral covalent organic framework material, preparation method and application

A covalent organic framework and chirality technology, applied in the field of chiral covalent organic framework materials, can solve the problems of low modification efficiency, complex synthesis of chiral monomers, lack of universality of chiral induction strategies, etc. Selective, high-yield effects

Pending Publication Date: 2022-06-28
SHANDONG NORMAL UNIV
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  • Abstract
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  • Claims
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Problems solved by technology

In the process of chiral covalent organic framework construction, it is necessary to balance the relationship between the crystallinity, stability and chiral structure of the covalent organic framework. There are still many problems in the efficient construction of chiral covalent organic framework: The synthesis is often complicated, the efficiency of chiral post-modification is low, and the chiral induction strategy lacks universality, etc.

Method used

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  • Chiral covalent organic framework material, preparation method and application
  • Chiral covalent organic framework material, preparation method and application
  • Chiral covalent organic framework material, preparation method and application

Examples

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Embodiment 1

[0049] Example 1: This example provides a method for preparing a chiral covalent organic framework material (Λ)-TpPa-1, the specific steps are as follows, 1,3,5-triformyl-2,4,6-m-benzenetri Phenol (63.0 mg, 0.30 mmol), p-phenylenediamine (48.6 mg, 0.45 mmol), S-2-methylpyrrolidine (7.7 mg, 0.09 mmol), dissolved in dichloromethane (6.0 mL), and reacted at room temperature 7 days. After the reaction, centrifuged to obtain brick red powder, washed with dichloromethane until the clear liquid was colorless, then washed once with ethanol, acetone, and ether in turn, and vacuum-dried at 60 ° C for 12 hours to obtain a chiral covalent organic framework material ( Δ)-TpPa-1. The structural formula of embodiment 1 sees figure 1 , powder diffraction PXRD see figure 2 , see circular dichroism CD spectrum image 3 , see SEM Figure 4 , see the infrared spectrum Figure 5 , see macro photo Image 6 .

Embodiment 2

[0050] Embodiment 2: This embodiment provides a method for preparing a chiral covalent organic framework material (Δ)-TpPa-1, the specific steps are as follows, 1,3,5-triformyl-2,4,6-m-benzenetri Phenol (63.0mg, 0.30mmol), p-phenylenediamine (48.6mg, 0.45mmol), R-2-methylpyrrolidine (7.7mg, 0.09mmol), dissolved and dispersed in dichloromethane (6.0mL), reacted at room temperature 7 days. After the reaction, centrifuged to obtain brick red powder, washed with dichloromethane until the clear liquid was colorless, then washed once with ethanol, acetone, and ether in turn, and vacuum-dried at 60 ° C for 12 hours to obtain a chiral covalent organic framework material ( Δ)-TpPa-1. The structural formula of embodiment 2 sees Figure 7 , powder diffraction PXRD see Figure 8 , see circular dichroism CD spectrum Figure 9 , see SEM Figure 10 , see the infrared spectrum Figure 11 , see macro photo Figure 12 .

Embodiment 3

[0051] Embodiment 3: This embodiment provides a method for preparing a chiral covalent organic framework material (Λ)-TpPa-2, the specific steps are as follows, 1,3,5-triformyl-2,4,6-m-benzenetri Phenol (63.0 mg, 0.30 mmol), p-phenylenediamine (61.0 mg, 0.45 mmol), S-2-methylpyrrolidine (7.7 mg, 0.09 mmol), dissolved in dichloromethane (6.0 mL), and reacted at room temperature 7 days. After the reaction, centrifuged to obtain brick red powder, washed with dichloromethane until the clear liquid was colorless, then washed once with ethanol, acetone, and ether in turn, and vacuum-dried at 60 ° C for 12 hours to obtain a chiral covalent organic framework material ( Δ)-TpPa-2. The structural formula of embodiment 3 sees Figure 13 , powder diffraction PXRD see Figure 14 , see circular dichroism CD spectrum Figure 15 , see SEM Figure 16 , see the infrared spectrum Figure 17 , see macro photo Figure 18 .

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Abstract

The invention belongs to the field of chiral covalent organic framework materials, and relates to a novel method for preparing a chiral covalent organic framework material through asymmetric catalysis and application of the chiral covalent organic framework material. The preparation method specifically comprises the following steps: by taking chiral small molecule (S / R)-2-methylpyrrolidine as a catalyst and 1, 3, 5-triformyl-2, 4, 6-phloroglucinol and an amino compound as construction units, carrying out asymmetric reaction to prepare a series of propeller chiral covalent organic framework materials. And the catalyst is used as a carrier of bivalent copper ions and is used for efficiently catalyzing an asymmetric A3 coupling reaction.

Description

technical field [0001] The invention specifically relates to a chiral covalent organic framework material, a preparation method and application, and belongs to the field of chiral covalent organic framework materials. Background technique [0002] Chiral covalent organic frameworks (CCOFs) are a new growth point in the field of chemistry and materials, and their applications in the field of heterogeneous asymmetric catalysis are in the ascendant. Therefore, CCOF materials are ideal models for the construction of novel chiral heterogeneous catalytic systems, which are expected to break through the technical bottleneck of traditional asymmetric catalysis of "high ee value at the expense of yield". During the construction of chiral covalent organic frameworks, the relationship between crystallinity, stability and chiral structure of covalent organic frameworks must be balanced. There are still many problems in the efficient construction of chiral covalent organic frameworks: T...

Claims

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Application Information

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IPC IPC(8): C08G12/08C08G12/06
CPCC08G12/08C08G12/06
Inventor 董育斌姚丙建李飞王道正
Owner SHANDONG NORMAL UNIV
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