Perylene diimide bridged double β-cyclodextrin stationary phase and its preparation method and application

A technology of perylene diimide-based bridge and cyclodextrin, which is applied in the field of chiral separation materials, can solve the problem of small improvement in stationary phase selectivity, unfavorable cyclodextrin inclusion effect, difficult to control quantity and site, etc. problem, to achieve good separation effect, improve synergistic inclusion and chiral separation ability, and good application prospects.

Active Publication Date: 2022-05-20
NANCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, if there are too few mono-derivatization groups, the effect of improving the selectivity of the stationary phase is small; partial derivatization is not easy to control the number and sites of participating reactive groups, and the chromatographic reproducibility is poor; full derivatization makes the original hydroxyl groups almost completely covered. Replacement, resulting in damage to the hydrogen bond, congestion of the cyclodextrin port, etc., which is not conducive to fully exerting the inclusion effect of the cyclodextrin

Method used

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  • Perylene diimide bridged double β-cyclodextrin stationary phase and its preparation method and application
  • Perylene diimide bridged double β-cyclodextrin stationary phase and its preparation method and application
  • Perylene diimide bridged double β-cyclodextrin stationary phase and its preparation method and application

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Embodiment 1

[0026] A preparation method of perylene diimide bridged double β-cyclodextrin stationary phase, comprising the following steps:

[0027] (1) Mix 1.7mmol 6-monoethylenediamine-β-cyclodextrin, 0.7mmol perylenetetracarboxylic dianhydride, 1.0mmol anhydrous zinc acetate and 120mL pyridine, stir to form a homogeneous solution, and under nitrogen protection, React in an oil bath at 100°C for 48 hours, then distill off the solvent under reduced pressure, add 100mL of water to dissolve the solid residue, filter, collect the filtrate, concentrate the filtrate to 1 / 3 of the original volume, add methanol to produce a large amount of precipitation, suction filter, vacuum the solid After drying, a purple-red product (perylene diimide bridged bis-cyclodextrin) was obtained;

[0028] (2) Dissolve the bridged bis-β-cyclodextrin synthesized above in 40 mL of anhydrous N,N-dimethylformamide (DMF) under magnetic stirring, and slowly add 3-isocyanato group at room temperature Propyltriethoxysila...

Embodiment 2

[0034] A preparation method of perylene diimide bridged double β-cyclodextrin stationary phase, comprising the following steps:

[0035] (1) Mix 2.0mmol 6-monoethylenediamine-β-cyclodextrin, 1.0mmol perylenetetracarboxylic dianhydride, 1.0mmol anhydrous zinc acetate and 120mL pyridine, stir to form a homogeneous solution, and under nitrogen protection, React in an oil bath at 100°C for 48 hours, then distill off the solvent under reduced pressure, add 100mL of water to dissolve the solid residue, filter, collect the filtrate, concentrate the filtrate to 1 / 3 of the original volume, add methanol to produce a large amount of precipitation, suction filter, vacuum the solid After drying, a purple-red product (perylene diimide bridged bis-cyclodextrin) was obtained;

[0036] (2) Dissolve the bridged bis-β-cyclodextrin synthesized above in 40 mL of anhydrous N,N-dimethylformamide (DMF) under magnetic stirring, and slowly add 3-isocyanato group at room temperature Propyltriethoxysila...

Embodiment 3

[0042] A preparation method of perylene diimide bridged double β-cyclodextrin stationary phase, comprising the following steps:

[0043] (1) Mix 2.3mmol 6-monoethylenediamine-β-cyclodextrin, 1.3mmol perylenetetracarboxylic dianhydride, 1.0mmol anhydrous zinc acetate and 120mL pyridine, stir to form a homogeneous solution, and under nitrogen protection, React in an oil bath at 100°C for 48 hours, then distill off the solvent under reduced pressure, add 100mL of water to dissolve the solid residue, filter, collect the filtrate, concentrate the filtrate to 1 / 3 of the original volume, add methanol to produce a large amount of precipitation, suction filter, vacuum the solid After drying, a purple-red product (perylene diimide bridged bis-cyclodextrin) was obtained;

[0044] (2) Dissolve the bridged bis-β-cyclodextrin synthesized above in 40 mL of anhydrous N,N-dimethylformamide (DMF) under magnetic stirring, and slowly add 3-isocyanato group at room temperature Propyltriethoxysila...

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Abstract

The invention discloses a perylene diimide bridged double β-cyclodextrin stationary phase and its preparation method and application. The material uses perylene diimide bridged double β cyclodextrin as a ligand, SBA-15 is prepared from a silica gel matrix, the preparation method is simple, the conditions are mild, green and non-toxic, and the reproducibility is good; the prepared perylene diimide bridged double β-cyclodextrin stationary phase has better Enantioselectivity, relatively stable chromatographic performance, good synergistic inclusion and chiral separation ability, can simultaneously resolve acidic, basic, neutral and amphoteric chiral compounds, and can be applied to various chromatographic modes. A high-efficiency and multifunctional chiral separation material has good application prospects in the field of separation of chiral drugs and pesticides.

Description

technical field [0001] The invention belongs to the field of chiral separation materials, and in particular relates to a perylene diimide bridging double β-cyclodextrin stationary phase and a preparation method and application thereof. Background technique [0002] Chirality is a common phenomenon in nature, and chiral substances also widely exist in nature, which have a wide range of applications in chemistry, medicine, food, pesticides, etc. Although the enantiomers of chiral substances are similar in structure, they show obvious differences in physiological activity, biological toxicity and pharmacokinetics. Often only one of the enantiomers has the corresponding activity, while the other enantiomers have the corresponding activity. Enantiomers are not only inactive, but may even exhibit toxic side effects. [0003] In 1992, the US FDA implemented strict standards for the declaration and production of chiral drugs, and then Canada, Japan and the European Union implemente...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J20/26B01J20/29B01J20/30C08B37/16
CPCB01J20/29C08B37/0012B01J20/262
Inventor 李来生钟慧张天赐曾庆丽双亚洲李良
Owner NANCHANG UNIV
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