Preparation and application method of helical chiral all-cis poly 3,5-dimethylol-4-substituted phenylacetylene derivatives without chiral atoms

A technology of helical chirality and dimethylol, which is applied in the field of preparation of helical polymers, can solve the problems of little research and achieve good chiral resolution performance, simple operation and broad application prospects

Active Publication Date: 2020-04-07
HARBIN ENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the research on helical polyacetylene mainly focuses on the cis-trans polyacetylene with a relaxed main chain structure, while the all-cis helical polyphenylene vinylene has a very tight helical structure and has better structural rigidity and helical stability, but there are few related studies. , especially in chiral high-performance liquid chromatography has not yet seen the application

Method used

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  • Preparation and application method of helical chiral all-cis poly 3,5-dimethylol-4-substituted phenylacetylene derivatives without chiral atoms
  • Preparation and application method of helical chiral all-cis poly 3,5-dimethylol-4-substituted phenylacetylene derivatives without chiral atoms
  • Preparation and application method of helical chiral all-cis poly 3,5-dimethylol-4-substituted phenylacetylene derivatives without chiral atoms

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Embodiment 1

[0029] (1) Preparation of helical chiral all-cis polyacetylene DDOHPA without chiral atom:

[0030] Measure 50mL (R)-α-methylbenzylamine and bubbling with helium gas for 5 minutes. Weigh 0.50 g of non-optically active all-cis polyphenylene acetylene DDOHPA, and dissolve it in 50 ml (R)-α-methylbenzylamine after bubbling with helium at normal temperature and pressure to make a solution. Pour the solution into a dialysis bag (cellulose dialysis bag, molecular weight cutoff 5000). After the dialysis bag is sealed, the dialysis bag containing the solution is placed in a beaker containing 500 ml of tetrahydrofuran, the beaker is heated to 35 degrees Celsius, and the tetrahydrofuran is replaced every 1 hour. After changing three times, take out the dialysis bag and open it, use a dropper to take out the solution in the dialysis bag and drop it into 500ml methanol to precipitate and precipitate an orange-red precipitate. After centrifugation, the obtained precipitate is vacuum dried fo...

Embodiment 2

[0035] (1) Preparation method of helical chiral all-cis polyphenylene acetylene PhEDOHPA without chiral atom: Measure 50 mL (S)-α-methylbenzyl alcohol and bubbling with helium for 5 minutes. Weigh 0.50 g of non-optically active all-cis polyphenylene acetylene PhEDOHPA, and dissolve it in 50 ml of (S)-α-methylbenzyl alcohol after bubbling with helium at normal temperature and pressure to make a solution. Pour the solution into a dialysis bag (cellulose dialysis bag, molecular weight cutoff 5000). After the dialysis bag is sealed, the dialysis bag containing the solution is placed in a beaker containing 300 ml of toluene, the beaker is heated to 45 degrees Celsius, and the toluene is replaced every 45 minutes. After changing three times, take out the dialysis bag and open it, use a dropper to take out the solution in the dialysis bag and drop it into 500ml methanol to precipitate and precipitate an orange-red precipitate. After centrifugation, the obtained precipitate is vacuum d...

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Abstract

The invention provides a preparation method and an application method of chiral-atom-free helically chiral all-cis polyphenylacetylene derivative materials. The preparation method comprises: dissolving a non-optically active poly 3,5-dihydroxymethyl-4-substituted phenylacetylene derivative in a chiral solvent to prepare a solution, replacing the chiral solvent in the solution with an achiral solvent through a membrane permeation method, and carrying out precipitation washing to prepare a series of the chiral-atom-free all-cis helical poly 3,5-dihydroxymethyl-4-substituted phenylacetylene derivative materials with helical chirality and the corresponding coating type high-performance liquid chromatography chiral stationary phase. According to the present invention, the used chiral reagent ofthe preparation method can be repeatedly used, the preparation method has characteristics of low cost and simple operation, the chiral stationary phase has good chiral splitting performance, and themethod has broad application prospects.

Description

Technical field [0001] The invention relates to the preparation of a helical polymer and its application method, in particular to the preparation of a helical chiral all-cis poly 3,5-dimethylol-4-substituted phenylacetylene derivative without chiral atoms and Its application method. Background technique [0002] Chirality is derived from the phenomenon that human left and right hands are mirror-image enantiomers of each other and cannot overlap. Therefore, the phenomenon that a molecule or compound cannot align with its enantiomer is called chirality. Polysaccharides, proteins, nucleic acids, etc. in biomolecules are all chiral molecules. The isomerism of chiral compounds due to different spatial arrangements is called enantiomers. The chemical composition and physical properties of the enantiomers are the same, but the optical rotation of the two is completely opposite. Chirality is a phenomenon ubiquitous in nature. Studies have found that many chiral enantiomers have obvious...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F138/00C08F8/00C07C39/21C07F7/08C07F7/20C07C37/68B01D15/08B01J20/285
CPCB01D15/08B01J20/285C07C37/685C07F7/20C08F8/00C07C39/21C08F138/00
Inventor 刘立佳顾缘缘王玉丹董红星白建伟
Owner HARBIN ENG UNIV
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