Chiral polysilsesquioxane containing arylidene in skeleton and preparation method and application thereof

A polysilsesquioxane and skeleton technology, which is applied in the field of chiral polysilsesquioxane and its preparation, can solve the problems of complicated preparation, lack of selective adsorption of aromatic compounds, etc., and achieves simple process route and convenient operation. , the effect of low cost

Active Publication Date: 2014-10-08
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesized ordered mesoporous organosilicon materials can selectively adsorb some heavy metal ions, but the disadvantage is that the preparation is cumbersome and post-treatment processes such as template removal are required.
In addition, so far, there is a lack of literature reports on the selective adsorption of aromatic compounds in the field

Method used

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  • Chiral polysilsesquioxane containing arylidene in skeleton and preparation method and application thereof
  • Chiral polysilsesquioxane containing arylidene in skeleton and preparation method and application thereof
  • Chiral polysilsesquioxane containing arylidene in skeleton and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1: Preparation of chiral polysilsesquioxane LL-P1 containing biphenylene.

[0046] (1) Acylation reaction of Boc-L-Val with 4,4'-biphenylenediamine:

[0047] Weigh 18.68 g (85.9 mmol) of Boc-L-Val into a 2 L three-neck flask, add 400 mL of DMF and stir to dissolve. 38.0 g (100.3 mmol) of HBTU was heated and dissolved in DMF and added to a three-neck flask. After stirring at room temperature for half an hour, 18 mL of triethylamine (128 mmol) was added and stirred at room temperature for 1.5-2 hours. 7.36 g (39.9 mmol) of 4,4'-biphenylenediamine was heated and dissolved in DMF, then added to a three-necked flask, and stirred at room temperature for 1 hour. Then, the reaction system was reacted at 55° C. for 12 hours. The reaction solution was added to 1 L of deionized water to precipitate a precipitate, filtered, and the filter cake was washed with deionized water until colorless, dried, and recrystallized with ethanol to obtain compound BLV-1 (light yellow so...

Embodiment 2

[0056] Example 2: Preparation of chiral polysilsesquioxane DD-P1 containing biphenylene.

[0057] (1) Reaction of Boc-D-Val with 4,4'-biphenylenediamine:

[0058] Weigh 18.68 g of Boc-D-Val (85.9 mmol) into a 2 L three-neck flask, add 400 mL of DMF and stir to dissolve. 38.0 g of HBTU (100.3 mmol) was heated and dissolved in DMF and added to a three-neck flask. After stirring at room temperature for half an hour, 18 mL of triethylamine (128 mmol) was added and stirred at room temperature for 1.5-2 hours. 7.36 g (39.9 mmol) of 4,4'-biphenylenediamine was heated and dissolved in DMF, then added to a three-necked flask, and stirred at room temperature for one hour. React at 55°C for 12 hours. The reaction solution was added to 1 L of deionized water to precipitate a precipitate, filtered, and the filter cake was washed with deionized water until it was colorless, dried and recrystallized with ethanol to obtain compound BDV-1 (light yellow solid, yield: 91.85%).

[0059] (2) De...

Embodiment 3

[0067] Example 3: Preparation of chiral polysilsesquioxane LL-P2 containing phenylene.

[0068] (1) Acylation reaction of Boc-L-Val with p-phenylenediamine:

[0069] Weigh 18.68 g (85.9 mmol) of Boc-L-Val into a 2 L three-neck flask, add 400 mL of DMF and stir to dissolve. 38.0 g (100.3 mmol) of HBTU was heated and dissolved in DMF and added to a three-neck flask. After stirring at room temperature for half an hour, 18 mL (128 mmol) of triethylamine was added and stirred at room temperature for 1.5 to 2 hours. Heat and dissolve 8.65 g (80 mmol) of p-phenylenediamine in DMF, add it into a three-necked flask, and stir at room temperature for 1 hour. React at 55°C for 12 hours. The reaction solution was added to 1 L of deionized water to precipitate a precipitate, filtered, and the filter cake was washed with deionized water until it was colorless, dried and recrystallized with ethanol to obtain compound BLV-2 (light yellow solid, yield: 89.5%).

[0070] (2) De-Boc group:

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Abstract

The invention provides chiral polysilsesquioxane containing arylidene in the skeleton and a preparation method and application thereof. The monomer of the chiral polysilsesquioxane has the following general formula: (EtO)3Si-(CH2)n-amino acid unit-aromatic perssad-amino acid unit-(CH2)n-Si(EtO)3, wherein n is any integer between 1 and 10, the amino acid unit comprises common amino acids like valine, isoleucine, alanine or phenylalanine, and the aromatic group is arylidene in diaminobenzene, biphenyl diamine, dipyridyl diamine, and bithiophene diamine. The chiral polysilsesquioxane has stable chemical properties, is simple to synthesize, is convenient to use, can well adsorb aryl compounds and heavy metal ions, and also has great application value in terms of chiral separation and chiral catalysis.

Description

technical field [0001] The invention belongs to the field of nanometer materials, and in particular relates to a chiral polysilsesquioxane containing an arylene group in a skeleton, a preparation method and an application thereof. Background technique [0002] Organic bridged polysilsesquioxane is a kind of hybrid material with special properties. In this kind of material, the inorganic component and the organic component are combined in the form of covalent bond through Si-C bond. This kind of material combines The characteristics of inorganic and organic substances, and the tunability of organic components make it exhibit a series of excellent properties, and have good application prospects in catalyst support, chromatographic separation and adsorption. [0003] Chinese patent CN102172518 B discloses a preparation method of a chiral stationary phase, the general formula of which is carrier-linking base-amino acid group-NH-(CH 2 ) n -NH-amino acid group-linker-carrier, wh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G77/26B01J20/26B01J20/30C07B57/00
Inventor 杨永刚李艺李宝宗王庆峰
Owner SUZHOU UNIV
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