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Oxidized helical conformation inverted thioether side chain-containing isocyanide spiral polymer and preparation method thereof

A helical conformation and polymer technology, which is applied in the field of isonitrile helical polymers and its preparation, can solve problems such as the application of complexes that cannot be helical, and achieve stimulating effects

Active Publication Date: 2018-08-14
HUBEI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In order to solve the defect that the compound with helical structure cannot be applied to the remaining medicines in the prior art, the present invention proposes an isocyanide helical polymer containing thioether side chains whose oxidized helical conformation is reversed, and its molecular structure contains formula I Repeating unit of the formula shown:

Method used

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  • Oxidized helical conformation inverted thioether side chain-containing isocyanide spiral polymer and preparation method thereof
  • Oxidized helical conformation inverted thioether side chain-containing isocyanide spiral polymer and preparation method thereof
  • Oxidized helical conformation inverted thioether side chain-containing isocyanide spiral polymer and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0036] (1) Preparation of S-benzyl-L-cysteine:

[0037]Add 2.42 g (0.02 mol) of L-cysteine ​​to a 250 ml four-neck flask, add 37.5 ml of 2.13 mol / L NaOH solution to dissolve it, control the temperature to 45 ° C, and then dropwise add 2.4 ml (0.02 mol ) of benzyl bromide, stirred thoroughly for 30 minutes, and adjusted the pH value with acetic acid diluent made of 10 ml acetic acid and 40 ml distilled water until the pH was 5.4, at which point a large amount of white precipitates precipitated. Stir well and filter with suction to obtain a white solid, which is then washed with distilled water, dried in a vacuum oven, and weighed to obtain 4.14 g of white solid powder with a yield of 97.6%, mp: 215.5-216.4 °C. IR (KBr, cm -1 ): 1619, 1568, 1493 (C=C on the benzene ring); 1394 (C-N); 698,768 (Ar-H).

[0038] The reaction equation of this process is as follows;

[0039]

[0040] (2) Preparation of S-benzyl-L-cysteine ​​methyl ester:

[0041] In a 100 ml four-neck flask, ad...

Embodiment 2

[0063] The specific implementation content in the second embodiment is the same as that of the first, but the difference is that the reaction temperature of the step (1) is 35°C; the molar ratio of formic acid and acetic anhydride in the formic acetic anhydride in the step (3) is 3; in the step (4) The molar ratio of dichloromethane and triethylamine is 2, and the molar ratio of triphosgene and dichloromethane is 0.5.

Embodiment 3

[0065] The specific implementation content in the third embodiment is the same as the first one, but the difference is that the reaction temperature of the step (1) is 65°C; the molar ratio of formic acid and acetic anhydride in the formic acetic anhydride in the step (3) is 10; in the step (4) The molar ratio of dichloromethane to triethylamine is 5, and the molar ratio of triphosgene to dichloromethane is 2.

[0066] The properties and structural characteristics of the materials prepared in Example 2 and Example 3 are the same or similar to those in Example 1.

[0067]The polymer containing the thioether structure synthesized by the invention has a helical structure and has redox stimulation responsiveness. Because it contains S atoms, it can be oxidized by oxidants to achieve redox stimulation. Such polyisonitrile helical polymers containing thioether structures can be used in the fields of chiral recognition, chiral separation, chiral signal amplification, asymmetric cata...

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Abstract

The invention provides an oxidized helical conformation inverted thioether side chain-containing isocyanide spiral polymer and a preparation method thereof, and belongs to the technical field of polymer synthesis. The polymer provided by the invention has a repeating unit of the structural formula represented by Formula I in a molecular structure, the formula is shown in the description, wherein Ris an alkyl and benzyl, and n is an integer of more than or equal to 10. The thioether structure-containing polymer synthesized by the invention is of a spiral structure and has redox stimuli responsiveness. Due to the presence of S atoms, the polymer can be oxidized by an oxidizing agent to achieve redox irritation. Such thioether structure-containing polyisocyanide spiral polymer can be used inthe fields of chiral recognition, chiral separation, chiral signal amplification, asymmetric catalysis and the like.

Description

technical field [0001] The invention belongs to the technical field of polymer synthesis, and in particular relates to an isocyanide helical polymer containing thioether side chains whose oxidized helix conformation is reversed and a preparation method thereof. Background technique [0002] In the middle of the 20th century, with the discovery of the DNA double helix structure and the important role of the helical structure in the activity of biological macromolecules, this kind of polymer has attracted the interest of a large number of scientists because of its special properties. After years of research, people have synthesized a large number of helical polymers and have achieved a large number of applications in many special fields such as asymmetric catalysis, chiral compound separation, material functionalization, and gel preparation. With the rise of intelligent materials science, the synthesis of helical polymers with chiral optical switches responsive to environmenta...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12
CPCC08G61/12C08G2261/11C08G2261/13C08G2261/1426C08G2261/145C08G2261/148C08G2261/334C08G2261/354
Inventor 吴诗郭丽媛黄胜堂张寒
Owner HUBEI UNIV OF SCI & TECH
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