Chiral porous organic polymer material and preparation method

A kind of polymer material and organic technology, applied in the field of preparation of chiral porous organic polymer materials, can solve the problems of not easy to modify chiral centers, low specific surface area, etc., achieve wide industrial application prospects, simple preparation method, low production cost low effect

Inactive Publication Date: 2016-07-27
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Previously reported binaphthol-based chiral porous polymer materials still have disadvantages such as low specific surface area and difficulty in modifying chiral centers.

Method used

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  • Chiral porous organic polymer material and preparation method
  • Chiral porous organic polymer material and preparation method
  • Chiral porous organic polymer material and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Under the protection of nitrogen, add 50 mg (0.10 mmol) of 3,3'-diphenyl-2,2'-binaphthol phosphoric acid, 35.5 μL (0.40 mmol) of dimethyl formal, and anhydrous 1,2 - Dichloroethane 2mL, stir to disperse evenly, then heat up to 50°C, add 64.9mg (0.40mmol) of anhydrous ferric chloride to the reaction bottle, and react at 50°C for 48 hours; after the reaction, filter the solid-liquid mixture , the obtained brown or black solid was washed three times with tetrahydrofuran, and then washed three times with 10-30 mL of methanol, water, dichloromethane, and acetone respectively; the obtained solid was extracted by Soxhlet with acetone for 4 hours, and finally depressurized After drying, a brown chiral porous organic polymer material was obtained. Its Fourier transform infrared spectrum (IR) is as follows figure 1 Shown, nitrogen adsorption-desorption isotherm (77K) as Figure 7 shown.

Embodiment 2

[0032] Under nitrogen protection, 50 mg (0.09 mmol) of 3,3'-bis-(4-methoxy)-phenyl-2,2'-binaphthol phosphoric acid, 32 μL (0.36 mmol), 2 mL of anhydrous 1,2-dichloroethane, stirred to disperse evenly, then heated up to 50°C, added 58mg (0.36mmol) of anhydrous ferric chloride to the reaction bottle, and reacted at 50°C for 48 hours; After the end, filter the solid-liquid mixture to obtain a brown or black solid, wash the solid three times with tetrahydrofuran, and then wash three times with 10-30 mL of methanol, water, dichloromethane, and acetone respectively; Extract for 4 hours, and finally dry under reduced pressure to obtain a brown chiral porous organic polymer material.

Embodiment 3

[0034] Under the protection of nitrogen, add 50 mg (0.083 mmol) of 3,3'-di-2-naphthyl-2,2'-binaphthol phosphoric acid, 29.5 μL (0.33 mmol) of dimethyl formal, and anhydrous 2mL of 1,2-dichloroethane, stir to disperse evenly, then heat up to 50°C, add 54.1mg (0.33mmol) of anhydrous ferric chloride to the reaction bottle, and react at 50°C for 48 hours; after the reaction, filter Solid-liquid mixture, the obtained brown or black solid was washed three times with tetrahydrofuran, and then washed three times with 10-30 mL of methanol, water, dichloromethane and acetone respectively; the obtained solid was extracted with acetone for 4 hours, Finally, it was dried under reduced pressure to obtain a brown chiral porous organic polymer material.

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Abstract

The invention discloses a chiral porous organic polymer material and a preparation method, and belongs to the technical field of chemical and novel materials.The preparation method comprises the steps that a 3,3'-substitued binaphthol phosphate compound and / or an aromatic ring compound and / or a condensed ring compound and / or a heterocyclic ring compound are subjected to a Friedel-Crafts alkylation reaction at the temperature of 30 DEG C-120 DEG C under the action of a lewis acid catalyst in the presence of a formaldehyde dimethyl acetal cross-linking agent, and then the chiral porous organic polymer material with the specific surface area of 3-3000 m<2> / g.According to the chiral porous organic polymer material and the preparation method, by changing the components serving as reaction monomers, the specific surface area and pore parameters of the obtained chiral porous organic polymer material and the variety and content of binaphthol can be adjusted, and the product can be applied to the heterogeneous asymmetric catalyzing field by serving as a heterogeneous catalyst, has the advantages of being easy to operate, mild in reaction condition and the like, is low in cost of the raw materials and production cost and has the wide industrial application prospect.

Description

technical field [0001] The invention belongs to the technical field of chemistry and new materials, and in particular relates to a preparation method of a chiral porous organic polymer material. Background technique [0002] Compared with homogeneous catalysis, heterogeneous catalysis has been widely valued because it can conveniently realize the separation, recovery and reuse of products and catalysts. Heterogeneous catalysts are usually loaded on a certain carrier or the framework itself has a certain catalytic function. There are many types of supports used in heterogeneous catalysis, such as carbon supports, silicon supports, oxide supports, and organic polymer supports. These support materials have their own unique properties and are widely used in the field of heterogeneous catalysis. In recent years, with the development of material science, some new materials, such as graphene, carbon nanotubes, metal-organic framework materials and covalently bonded porous organic ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12B01J31/06C07D265/36C07D215/06C07D215/12C07D215/14
CPCB01J31/061B01J2231/646C07D215/06C07D215/12C07D215/14C07D265/36C08G61/12C08G61/124C08G61/126C08G2261/314C08G2261/3223C08G2261/3241C08G2261/3247C08G2261/45
Inventor 刘晓明张雨薇夏虹
Owner JILIN UNIV
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