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Application of C=C bond connection-based COF material in preparation of chiral chromatographic stationary phase

A chiral stationary phase and chiral chromatography technology, applied in the application field of making chiral chromatographic stationary phases, can solve the problems of strict conditions of use, single type of separation substrate, etc., to broaden design ideas, high chiral selectivity, good The effect of chiral separation performance

Active Publication Date: 2021-12-21
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The present invention improves the problems of the existing chiral stationary phases with strict conditions of use and relatively single types of separated substrates, and has broad development and application prospects

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  • Application of C=C bond connection-based COF material in preparation of chiral chromatographic stationary phase
  • Application of C=C bond connection-based COF material in preparation of chiral chromatographic stationary phase
  • Application of C=C bond connection-based COF material in preparation of chiral chromatographic stationary phase

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preparation example Construction

[0060] In one embodiment of the present invention, the preparation method of COF material based on C=C bond connection, the steps are as follows:

[0061] Mix crown ether functionalized bis-naphthalene tetraaldehyde-based monomers, terephthalonitrile or 4,4'-biphenyldiacetonitrile, dioxane, and methanol, heat to the reaction temperature under vacuum-sealed conditions, and perform the reaction. After the reaction, the mixture was cooled to room temperature and filtered to obtain a powdery solid, which was then washed and dried to obtain COF-1 or COF-2.

[0062] In one embodiment of the present invention, based on the preparation method of C=C bond-linked COF materials, an exemplary implementation condition is given:

[0063] Crown ether functionalized bis-naphthyl tetraaldehyde monomer (30 mg, 0.027 mmol), terephthalonitrile (8.3 mg, 0.053 mmol) or 4,4'-biphenyl diacetonitrile (12.4 mg, 0.053 mmol), Dioxane (0.5 mL), methanol (0.5 mL) were mixed in a 10 mL Schlenk tube. The S...

Embodiment 1

[0085] Preparation of high stability COF-1:

[0086] In a 10 mL Schlenk tube, 30 mg of a crown ether functionalized bis-naphthyl backbone tetraaldehyde monomer, 8.3 mg of terephthalonitrile, 0.5 mL of dioxane, and 0.5 mL of methanol were mixed. The Schlenk tube was vacuum sealed and heated to 120°C for a reaction time of 4 days. The mixture was cooled to room temperature and filtered to obtain a powdery solid, which was washed three times with deionized water, tetrahydrofuran and ether, and dried under vacuum at 60°C overnight to obtain 28 mg of light yellow COF-1 powder.

Embodiment 2

[0088] Preparation of high stability COF-2:

[0089] In a 10 mL Schlenk tube, 30 mg of the tetraaldehyde monomer of the crown ether functionalized bis-naphthalene backbone, 12.4 mg of 4,4'-biphenyldiacetonitrile, 0.5 mL of dioxane, and 0.5 mL of methanol were mixed. The Schlenk tube was vacuum sealed and heated to 120°C for a reaction time of 4 days. The mixture was cooled to room temperature, filtered to obtain a powdery solid, washed three times with deionized water, tetrahydrofuran and diethyl ether, and dried under vacuum at 60°C overnight to obtain 29 mg of light yellow COF-2 powder.

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Abstract

The invention relates to application of aC=C bond connection-based COF material in preparation of a chiral chromatographic stationary phase. The preparation method comprises the following steps: synthesizing chiral COF connected with a C=C bond by using a crown ether functionalized dinaphthalene tetraaldehyde monomer on the basis of a Knoevenagel condensation reaction; compounding COF and silica gel by using a net package method to prepare a high performance liquid chromatography chiral stationary phase; uniformly coating COF on a gas chromatographic column by using a dynamic coating method so as to be used as a gas chromatographic chiral stationary phase; and applying the high performance liquid chromatographic column or gas chromatographic column to separate various racemic compounds. Compared with the prior art, due to the high stability of the synthesized C=C bond connection COF, the liquid chromatographic column and the gas chromatographic column prepared in the invention both show good separation capability and durability in the chiral separation process, so that the problem that the existing chiral stationary phase is only suitable for a specific chromatography is solved, a novel high-performance chiral separation material which can be used for liquid chromatography and gas chromatography at the same time is developed, and potential application prospects are achieved.

Description

technical field [0001] The invention relates to the field of chiral chromatographic separation, in particular to the application of a COF material connected by a C=C bond for making a chiral chromatographic stationary phase. Background technique [0002] Chirality is one of the basic properties of nature. Chiral compounds are involved in all aspects of human life, especially the pharmaceutical industry, food industry and pesticide industry. The pharmacological effects of the two enantiomers in a chiral drug are often different, and sometimes even diametrically opposed. Therefore, realizing the separation of optically pure monochiral compounds is of great significance to human beings that cannot be ignored. Chromatographic separation is one of the most common and popular chiral separation methods. At present, scientists have developed a variety of chiral stationary phases for chiral chromatographic separation, some of which have been commercialized . But so far, the same c...

Claims

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Application Information

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IPC IPC(8): B01J20/29B01J20/30B01D15/20B01D15/38B01D53/02
CPCB01J20/29B01D15/206B01D15/3833B01D53/025
Inventor 崔勇袁晨刘玉豪刘燕
Owner SHANGHAI JIAO TONG UNIV
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