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First-class purpurin ion monomers and preparation method and application thereof

A technology of ionic monomer and viologen, which is applied in the field of viologen ionic monomer and its preparation, can solve the problems of insufficient rigidity, difficulty in synthesizing a porous framework structure with high specific surface area, etc., and achieve short reaction time, rich variety and excellent reaction conditions mild effect

Inactive Publication Date: 2019-06-28
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the viologen ionic monomers prepared by this method usually have flexible alkyl chains and are not rigid enough, so they are greatly restricted in the synthesis of ionic porous polymers, especially ordered ionic covalent organic framework materials. However, it is difficult to synthesize a porous framework structure with high specific surface area due to the limitation of

Method used

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  • First-class purpurin ion monomers and preparation method and application thereof
  • First-class purpurin ion monomers and preparation method and application thereof
  • First-class purpurin ion monomers and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: the preparation of viologen base Zincke salt VL-Br

[0025]

[0026] Weigh 4,4'-bipyridine (10mmol, 1.56g) and 1-bromo-2,4-dinitrobenzene (20mmol, 4.94g) in a reaction flask, add 100mL solvent acetonitrile, stir to make the raw materials completely dissolve. Then, the above solution was refluxed and stirred at 90° C. for 72 h. After the reaction, the resulting solid product was simply filtered, washed and dried to obtain a yellow solid, viologenyl Zincke salt VL-Br, with a yield of 90%. Characterized as follows:

[0027] 1 13C NMR( 100MHz, D2O): δ152.58, 149.81, 146.80, 142.77, 138.19, 131.11, 130.70, 127.54 and 122.77ppm. Elemental analysis: measured value: C, 40.85; H, 2.51; N, 12.83wt%. Theoretical value C22W14O8N9Br62(M. ): C, 40.64; H, 2.17; N, 12.93wt%.

Embodiment 2

[0028] Example 2: Preparation of aniline functionalized viologen ionic monomer

[0029]

[0030] Preparation of viologen ionic monomers functionalized with aniline groups: First, weigh Zincke salt VL-Br (10mmol, 6.50g) and p-phenylenediamine (20mmol, 2.16g) in a reaction flask, add 200mL solvent ethanol , stirred to disperse the raw materials evenly, and heated to reflux at 80°C for 48h. After the reaction, add 50 mL of water and stir for several hours, filter with a common funnel, the filtrate is dark brown, add 10 g of activated carbon and stir for 2 hours after the filtration, and then filter, the color of the filtrate becomes lighter. The filtrate was rotary evaporated under low pressure to remove water to obtain a dark brown solid, which was washed several times with tetrahydrofuran (THF). Finally dried in a vacuum oven to obtain dark brown solid product V-NH 2 -Br.

Embodiment 3

[0031] Embodiment 3: Preparation of benzonitrile functionalized viologen ionic monomer

[0032]

[0033] Preparation of benzonitrile-functionalized viologen ion monomer: First, weigh Zincke salt VL-Br (10mmol, 6.50g) and p-aminobenzonitrile (20mmol, 2.36g) in a reaction flask, add 200mL Solvent ethanol, stir to disperse the raw materials evenly, and heat to reflux at 80°C for 48h. After the reaction, add 50 mL of water and stir for several hours, filter with a common funnel, the filtrate is light brown, and the filtrate is rotated to remove water under low pressure to obtain a light brown solid, which is then washed several times with tetrahydrofuran (THF). Finally, it was dried in a vacuum oven to obtain a light brown solid product V-CN-Br.

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Abstract

The invention relates to first-class purpurin ion monomers and a preparation method and application thereof. The structural formula of each purpurin ion monomer is shown in the description, and the purpurin ion monomers are prepared by carrying out a Zincke reaction on a purpurin-based Zincke salt VL-Br and a para-aniline substituted by an R functional group in an organic solvent. According to thedemands of practical application, different kinds of the purpurin ion monomers with specific substitutional functional groups can be designed and prepared. The preparation method has the advantages that the required reaction conditions are mild, the reaction time is short, applied equipment is simple, and the preparation method is suitable for large-scale application. The purpurin ion monomers can be used for preparing purpurin-based porous ionic polymer materials, and the type of multifunctional purpurin ionic monomers is diversified.

Description

technical field [0001] The invention relates to the preparation and application of compounds, in particular to a viologen ion monomer and its preparation method and application. Background technique [0002] Viologen is the good name of 1,1'-disubstituent-4,4'-bipyridyl salt, it can change from colorless to purple when it is reduced, so it is called viologen. There are two N cation centers in the viologen structure, which can donate and accept electrons in different oxidation states or reduction states, and can undergo reversible redox reactions, accompanied by color changes. Recently, a series of functional viologen-based ionic porous organic polymers have been prepared by introducing the viologen structure into porous polymers, which have been applied in many fields (ACS Appl. Mater. Interfaces, 2019, 11 , 6705-6716). [0003] At present, the preparation method of viologen ion monomer mainly relies on the Menschutkin reaction, that is, the quaternization reaction between...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/02C07F5/02
Inventor 孙梦瑶陈国建沈洁黄小慧张亚东张珂黄蕊
Owner XUZHOU NORMAL UNIVERSITY
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