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Chiral triptycene polyimide film and its preparation method and application of chiral molecular separation

A technology of pterene polyimide and chiral molecules, which is applied in the field of separation of chiral molecules, and can solve problems such as the few researches on chiral thin films, the problem of polymer solubility, and the difficulty in post-processing of materials.

Active Publication Date: 2020-10-16
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But so far, there are only a handful of studies on the preparation of chiral thin films from porous organic polymers. The main reason is the solubility of many polymers, which makes it difficult to carry out post-processing of materials.

Method used

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  • Chiral triptycene polyimide film and its preparation method and application of chiral molecular separation
  • Chiral triptycene polyimide film and its preparation method and application of chiral molecular separation
  • Chiral triptycene polyimide film and its preparation method and application of chiral molecular separation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: Synthesis of R-triptycene hexafluoropolyimide with R-configuration 2,6-diaminotriptycene and hexafluorodianhydride.

[0034] Dissolve R-configuration 2,6-diaminotriptycene (550mg, 1.9mmol) and hexafluorodianhydride (851mg, 1.9mmol) in N-methylpyrrolidone (10ml), under argon atmosphere, 25°C Reaction 24h. Pyridine (1.5ml) and acetic anhydride (2.5ml) were added, and the reaction was continued for 1h. Then the temperature was raised to 110°C, and the reaction was carried out for 24 hours. The reaction was terminated, and the reaction solution was cooled and then poured into methanol (300ml) for precipitation, and the precipitate was collected and purified by Soxhlet extraction of methanol solution to obtain pure R-triptycene hexafluoropolyimide.

[0035] R-triptycene hexafluoropolyimide was dissolved in tetrahydrofuran and detected by gel permeation chromatography (GPC), and its degree of polymerization n was 38.

Embodiment 2

[0036] Example 2: S-configuration 2,6-diaminotriptycene and hexafluorodianhydride to synthesize S-triptycene hexafluoropolyimide.

[0037] Dissolve S-configuration 2,6-diaminotriptycene (550mg, 1.9mmol) and hexafluorodianhydride (851mg, 1.9mmol) in N-methylpyrrolidone (10ml), under argon atmosphere, 25°C React for 24 hours. Pyridine (1.5ml) and acetic anhydride (2.5ml) were added and the reaction was continued for 1 hour. Then the temperature was raised to 110° C., and the reaction was carried out for 24 hours. Terminate the reaction, and pour the reaction solution into methanol (300ml) for precipitation after it is cooled, collect the precipitate and carry out the Soxhlet extraction step of methanol solution for purification to obtain pure S-triptycene hexafluoropolyimide.

[0038] S-triptycene hexafluoropolyimide was dissolved in tetrahydrofuran and detected by gel permeation chromatography (GPC), and its degree of polymerization n was 66.

Embodiment 3

[0039] Example 3: Circular Dichroism Detection of R-triptycene hexafluoropolyimide and S-triptycene hexafluoropolyimide

[0040] R-triptycene hexafluoropolyimide and S-triptycene hexafluoropolyimide were respectively prepared into 0.2mg / ml tetrahydrofuran solutions, and then added into a detection cell with a thickness of 1mm for testing. as attached figure 1 As shown, the obtained two circular dichroism chromatograms have good symmetry and obvious peak shape, which indicates that the polymer structure contains a chiral structure, and chiral triptycene has been embedded in the polymer structure.

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Abstract

The invention belongs to the technical field of polymer film separation, and discloses preparation and application of two chiral triptycene polyimide films. The preparation comprises the steps of (1)carrying out polymerization reaction on a dianhydride monomer compound and optical pure 2,6-diaminotriptycene to obtain two chiral triptycene polyimide; (2) preparing a chiral film by a solvent evaporation method; and (3) separating racemation micromolecules by the chiral film through a racemation film experiment. The preparation has the advantages of low material cost, simple film making method,outstanding chiral separation effect and the like, and has large application prospect in the aspect of chiral resolution and the like.

Description

technical field [0001] The invention belongs to the technical field of polymer membrane separation, and specifically relates to the synthesis and preparation of two chiral polyimides to obtain a chiral thin film, which can be used for the separation of chiral molecules. Background technique [0002] Chiral molecules, that is, chemical molecules with chiral centers, form a pair of enantiomers that are mirror images of each other, and chiral centers can be formed directly from chiral carbons to form enantiomers, such as sugars. It can also be the stereo configuration of chemical molecules that leads to the formation of chiral centers, such as the binaphthol structure. Many physical and chemical properties of enantiomers are very similar, but in medicine, the pharmacokinetics exhibited by enantiomers often make these enantiomers exhibit different pharmacological and toxicological behaviors in vivo . In human history, medical accidents have also been caused by chiral drugs, an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G73/10C08L79/08
CPCB01D67/0002B01D69/02B01D71/64B01D2325/22B01D2325/34C08G73/1067C08G73/1071C08J5/18C08J2379/08
Inventor 张春翟天龙陈静静马辉王震张青梅张清璞
Owner HUAZHONG UNIV OF SCI & TECH
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