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Temperature-sensitive spiral polyisocyanide derivative constructed by dynamic acylhydrazone bond and preparation method thereof

A temperature-sensitive helix and acylhydrazone bond technology, applied in the field of bionic intelligent materials, can solve problems such as difficulties and limited applications, and achieve the effects of low cost, simple and easy method, and excellent temperature-sensitive performance

Pending Publication Date: 2020-10-09
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There have been many reports on the research of helical polyisocyanates, but most of them have achieved the induction of polymer helical conformation in organic solvents, but it is very difficult in water, which limits its application in the biological field.

Method used

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  • Temperature-sensitive spiral polyisocyanide derivative constructed by dynamic acylhydrazone bond and preparation method thereof
  • Temperature-sensitive spiral polyisocyanide derivative constructed by dynamic acylhydrazone bond and preparation method thereof
  • Temperature-sensitive spiral polyisocyanide derivative constructed by dynamic acylhydrazone bond and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0034] In this embodiment, a method for preparing a temperature-sensitive helical polyisocyanate derivative constructed by a dynamic acylhydrazone bond, the steps are as follows:

[0035] a. Dissolve the methyl-terminated oligomeric alkoxyether base and 4-formamidobenzoic acid in DCM at a molar ratio of 1.25:1 after amino modification, carry out ice-salt bath to the mixed solution, and inert Under gas protection, 1-hydroxybenzotriazole (HOBt) was added in the mixed solution, and after stirring for 30 minutes, 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride ( EDC·HCl), its dosage is 1 time of the molar weight of the linear alkoxy ether unit; stir until the reaction is complete, after separation and purification, the obtained monomer and triethylamine are dissolved in DCM, and triphosgene is dissolved in In DCM, it was slowly added dropwise to the mixed liquid reaction system in an ice-salt bath, and after 30 minutes of reaction, NaHCO 3 solution, heated to 0°C, stir...

Embodiment 2

[0049] This embodiment is basically the same as Embodiment 1, especially in that:

[0050] In this example, dynamic acylhydrazone bonds are used to construct temperature-sensitive helical polyisocyanate derivatives, and small molecules of glutamic acid, alanine, phenylalanine, and leucine are used as chiral units. Induces a main-chain helical conformation. Or adjust the helical conformation of the polyisocyanate main chain by adjusting the temperature. The chirality of small molecules is transferred to the polyisocyanate main chain through dynamic acylhydrazone bonds, and the polyisocyanate is induced to form a helical structure through temperature-sensitive behavior. This type of polymer is suitable for applications in the fields of chiral compound separation and asymmetric catalysis.

[0051] In summary, the present invention utilizes the general-soldier principle to induce the helical conformation of the main chain with a small amount of chiral glutamic acid or other small...

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Abstract

The invention discloses a temperature-sensitive spiral polyisocyanide derivative constructed by a dynamic acylhydrazone bond and a preparation method thereof. The structural formula of the spiral polyisocyanide derivative is shown as the specification, wherein m = 0.9-0.95, and n = 1-m. The group R is dimethyl glutamate (Glu), alanine methyl ester (Ala), phenylalanine methyl ester (Phe) or leucinemethyl ester (Leu). According to the invention, the spiral conformation of the main chain is induced by using a small amount of chiral glutamic acid or other small molecules of amino acids with aldehyde groups by utilizing the principle of general-soldier, wherein the polyisocyanide derivative has excellent temperature-sensitive characteristics, and the polymer spiral conformation can be regulated and controlled through the temperature-sensitive phase change behavior. In addition, the orderliness of the spiral conformation also influences the temperature-sensitive behavior of the polymer. Theinvention of the novel polyisocyanide derivative provides a new thought for preparing a stimuli-responsive chiral material, and expands the application prospect of the polyisocyanide derivative in the field of intelligent materials.

Description

technical field [0001] The invention relates to a helical polymer and a preparation method thereof, in particular to a helical polyisocyanate derivative and a preparation method thereof, which are applied in the technical field of bionic intelligent materials. Background technique [0002] Macromolecules with a helical structure are very common in living organisms in nature, such as nucleic acids and proteins. Helical structures play an important role in realizing their biological functions. Biomimetic synthesis of helical polymers is very important for understanding and imitating the functions of biological macromolecules and developing new chiral materials. is of great significance. Synthetic helical polymers mainly include two types: dynamic helical polymers and static helical polymers. As the first reported polymer with a stable helical conformation, polyisocyanate has the characteristics of high rigidity and high-density packing, so the helical conformation of polyisoc...

Claims

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Application Information

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IPC IPC(8): C07C251/08C07C249/02C07C291/10C07C231/12C07C233/54C07C231/14C07C237/42
CPCC07C251/08C07C249/02C07C291/10C07C231/12C07C231/14C07C237/42C07C233/54
Inventor 张阿方肖莉吴迪武剑慧刘坤张夏聪李文
Owner SHANGHAI UNIV
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