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Preparation method and application of azobenzene diamido bridged beta-cyclodextrin chiral stationary phase

A technology of azophthalamide-based bridges and chiral stationary phases, which can be used in separation methods, chemical instruments and methods, and other chemical processes, and can solve problems such as port group crowding and inconvenient cavity inclusions , to achieve the effect of good reproducibility, low cost of raw materials and simple process

Active Publication Date: 2021-04-06
NANCHANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the derivatization of the port makes the port group crowded to a certain extent, which makes it difficult to fully exert the inclusion effect of the cavity.

Method used

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  • Preparation method and application of azobenzene diamido bridged beta-cyclodextrin chiral stationary phase
  • Preparation method and application of azobenzene diamido bridged beta-cyclodextrin chiral stationary phase
  • Preparation method and application of azobenzene diamido bridged beta-cyclodextrin chiral stationary phase

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Experimental program
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Effect test

Embodiment 1

[0029] (1) Azobenzene-4,4'-dicarboxylic acid (mmol): mono-6-amino-β-cyclodextrin (mmol): N, N'-dicyclohexylcarbodiimide (DCC, mmol ): 1-Hydroxybenzotriazole (HOBT, mmol): N, N-dimethylformamide (DMF, mL) was mixed at a ratio of 1.0:1.5:1.5:1.5:15, and reacted at room temperature for 48 hours to obtain the even A solution of β-cyclodextrin bridged by azophthalamide group, adding acetone to the above reaction solution to precipitate a precipitate, filter, dissolve the solid in water, and separate and purify through a carboxymethyl dextran gel (C-25) column, The eluent is added with acetone to precipitate the product, and dried to obtain the azobenzene-4,4'-dicarboxamido bridged β-cyclodextrin chiral ligand;

[0030] (2) Under the protection of nitrogen, dissolve the azophthalamide bridged β-cyclodextrin in anhydrous DMF, and then slowly add 0.4 mL of γ-isocyanatopropyl triethoxysilane to the above Solution, reacted at 80°C for 2 hours to obtain a reaction solution containing azob...

Embodiment 2

[0036] (1) Azobenzene-4,4'-dicarboxylic acid (mmol): mono-6-amino-β-cyclodextrin (mmol): DCC (mmol): HOBT (mmol): DMF (mL) according to 1.0 Mix in the ratio of 2.0:2.0:2.0:20, react at room temperature for 48 hours, and obtain a solution of azobenzenedicarboxamido bridged β-cyclodextrin, add acetone to the above reaction solution, precipitate precipitate, filter, and dissolve the solid in water , separated and purified by carboxymethyl dextran gel (C-25) column, the eluent was added with acetone to precipitate the product, and dried to obtain azobenzene-4,4'-dicarboxamido bridged β-cyclodextrin Chiral ligands;

[0037] (2) Under the protection of nitrogen, dissolve the azophthalamide bridged β-cyclodextrin in anhydrous DMF, and then slowly add 0.4 mL of γ-isocyanatopropyl triethoxysilane to the above Solution, reacted at 80°C for 2 hours to obtain a reaction solution containing azobenzene-4,4'-dicarboxamido bridged β-cyclodextrin triethoxysilane;

[0038] (3) Under the prote...

Embodiment 3

[0043] (1) Azobenzene-4,4'-dicarboxylic acid (mmol): mono-6-amino-β-cyclodextrin (mmol): DCC (mmol): HOBT (mmol): DMF (mL) according to 1.0 : 2.5:2.5:2.5:25 ratio mixing, reacting at room temperature for 48 hours, to obtain a solution of azobenzenedicarboxamido-bridged β-cyclodextrin, adding acetone to the above reaction solution to precipitate a precipitate, filter, and dissolve the solid in water , separated and purified by carboxymethyl dextran gel (C-25) column, the eluent was added with acetone to precipitate the product, and dried to obtain azobenzene-4,4'-dicarboxamido bridged β-cyclodextrin Chiral ligands;

[0044] (2) Under the protection of nitrogen, dissolve the azophthalamide bridged β-cyclodextrin in anhydrous DMF, and then slowly add 0.4 mL of γ-isocyanatopropyl triethoxysilane to the above Solution, reacted at 80°C for 2 hours to obtain a reaction solution containing azobenzene-4,4'-dicarboxamido bridged β-cyclodextrin triethoxysilane;

[0045] (3) Under the p...

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Abstract

The invention relates to the technical field of chiral stationary phases, in particular to a preparation method and an application of an azobenzene diamido bridged beta cyclodextrin chiral stationary phase. The azobenzene diamido bridged beta cyclodextrin is used as a second-generation supramolecular compound, azobenzene provides pi pi-pi action, amide is a hydrogen bond donor and also a hydrogen bond receptor, azo has a flexible structure, cooperation with a synergistic inclusion effect between two cyclodextrin cavities is facilitated, and the stability of the supramolecular compound is improved. The surface of a stationary phase prepared from the bridged cyclodextrin contains rich action sites, so that the spatial structure difference of levorotatory and dextrorotatory enantiomers can be comprehensively identified, more chiral substances can be split in a short time, the chiral separation efficiency is greatly improved, the method can be applied to normal-phase, reversed-phase and polar organic modes, the splitting range is widened, and good practical values are realized.

Description

technical field [0001] The invention relates to the technical field of chiral stationary phases, in particular to a preparation method and application of an azobenzenedicarboxamido bridged β-cyclodextrin chiral stationary phase. Background technique [0002] Chirality is a common phenomenon in nature, and chiral compounds are widely used in chemistry, medicine, food, pesticides, etc. According to authoritative research, among 1800 kinds of pesticides, 57% of active ingredients are chiral. The chirality problem caused by enantiomers has attracted widespread attention from the international community at the beginning of the 20th century. The blood lessons of the "thalidomide incident" have made people start to be vigilant and gradually realize that although the physical and chemical properties of enantiomers The properties are almost the same, but they may exhibit completely different biological activities, toxicity, toxicology, metabolic pathways and medicinal value when int...

Claims

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Application Information

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IPC IPC(8): B01J20/29B01J20/30B01D15/38
CPCB01J20/29B01D15/3833
Inventor 李来生张天赐钟慧双亚洲李良
Owner NANCHANG UNIV
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