Oxidoreduction responsive nanoparticles based on bisimidazole ionic liquids and preparation method of oxidoreduction responsive nanoparticles

An ionic liquid and nanoparticle technology, which is applied in the field of redox-responsive nanoparticles based on biimidazole ionic liquids and their preparation, can solve problems such as less nanogel materials, and achieve broad application prospects and good redox-responsiveness. Effect

Inactive Publication Date: 2014-09-17
NORTHWEST NORMAL UNIVERSITY
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  • Oxidoreduction responsive nanoparticles based on bisimidazole ionic liquids and preparation method of oxidoreduction responsive nanoparticles
  • Oxidoreduction responsive nanoparticles based on bisimidazole ionic liquids and preparation method of oxidoreduction responsive nanoparticles
  • Oxidoreduction responsive nanoparticles based on bisimidazole ionic liquids and preparation method of oxidoreduction responsive nanoparticles

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Embodiment 1

[0038](1) Synthesis of cross-linking agent DSDMA: Add anhydrous dichloromethane (150 mL), 2-(2-hydroxyethyl) disulfide (10.0024 g, 64.84 mmol) and triethylamine (54 mL) into a 250 mL one-necked flask , 38mmol), cooled in an ice-water bath, then added dropwise methacryloyl chloride (20.0791g, 192.09mmol), reacted in an ice-water bath for 30min, and then reacted at room temperature for 24h. After the reaction was completed, triethylamine hydrochloride was removed by filtration, the solvent was removed by rotary evaporation, and then dissolved in chloroform, washed three times with 0.1M sodium carbonate aqueous solution, then washed three times with water, the organic phase was dried with anhydrous magnesium sulfate, and finally the solvent was removed under reduced pressure. Chloroform. Separation by column chromatography through petroleum ether / dichloromethane (1 / 2 (v / v) to obtain a light yellow transparent liquid product 2-(2-ethyl methacrylate) disulfide;

[0039] (2) Prepar...

Embodiment 2

[0043] (1) Synthesis of cross-linking agent DSDMA: same as Example 1;

[0044] (2) Preparation of biimidazole ionic liquid monomer: same as Example 1;

[0045] (3) Preparation of redox-responsive nanoparticles: [BIm-4C]Br (0.5007g, 1.237mmol) and DSDMA (0.0195g, 0.066mmol) were added to a 100mL round bottom flask, and the initiator azo Isobutyronitrile AIBN (0.0073g, 0.044mmol), then add 50mL of absolute methanol, N 2 Under protection, stir and react at 70±5°C for 5.5 hours. After the polymerization, the liquid is added to diethyl ether to precipitate to obtain a solid powder, which is fully washed with diethyl ether and dried in vacuum. The particle size of the nanoparticles was determined to be 441nm by dynamic light scattering experiments, and the particle size of the nanoparticles changed to 449.2nm after adding the reducing agent, which has redox responsiveness.

[0046] Its structural formula is the same as that of Example 1; in the formula, n=2, a=c=28; b=d=1.

Embodiment 3

[0048] (1) Synthesis of cross-linking agent DSDMA: same as Example 1;

[0049] (2) Preparation of biimidazole ionic liquid monomer: Mix 1-vinylimidazole and 1,6-dibromohexane at a molar ratio of 2.5:1, add to a 100 mL round bottom flask, and then add 50 mL absolute Methanol, in N 2 Under protection, the reaction was stirred and refluxed at 85°C for 48 h. After the reaction, the mixture was added to 150 mL of diethyl ether to settle and washed 2-3 times with diethyl ether. The product was placed in a vacuum oven and dried at room temperature for 24 h to obtain biimidazolium bromide ionic liquid 1,6-hexyl-3,3 '-Di-1-vinylimidazolium bromide [BIm-6C]Br, yield: 64.8%.

[0050] (3) Preparation of redox-responsive nanoparticles: [BIm-6C]Br (0.4973g, 1.157mmol) and DSDMA (0.0375g, 0.1157mmol) were added to a 100mL round bottom flask, and the initiator azo Isobutyronitrile AIBN (0.0189g, 0.115mmol), then add 50mL of absolute methanol, N 2 Under protection, the mixture was stirred ...

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Abstract

The invention provides an oxidoreduction responsive nanoparticles based on bisimidazole ionic liquids and a preparation method of the oxidoreduction responsive nanoparticles, and belongs to the field of materials. According to the method, the crosslinking copolymerization is carried out in a selective solvent in one step by utilizing bisimidazole ionic liquid monomers and a cross-linking agent containing disulfide bonds as raw materials, so that the nanoparticles with oxidoreduction responsiveness are prepared. After the stimulating responsiveness of the nanoparticles is analyzed by utilizing a dynamic light scattering experiment, the result shows that the nanoparticles based on bisimidazole ionic liquids have the good oxidoreduction responsiveness, so that the nanoparticles provided by the invention have wide application prospects in the fields of medicine release, enzyme immobilization, catalysis and the like.

Description

technical field [0001] The invention belongs to the field of new materials, and relates to the preparation of a redox-responsive nano-ion, in particular to a redox-responsive nano-particle based on a biimidazole ionic liquid and a preparation method thereof. Background technique [0002] Smart polymers are often called "environment-sensitive polymers", "stimuli-responsive polymers" and so on. When it is stimulated by physical, chemical or even biological signal changes in the external environment, the physical or chemical properties of the polymer will mutate. Most of the polymer research systems are their aqueous solutions and hydrogels. Traditional hydrogels are not sensitive to changes in the external environment; smart hydrogels have the characteristics of external field response, and can respond to changes in the external environment (such as temperature, pH value, salt concentration, light, electromagnetic field, solvent or chemical substances, etc.) Respond to these...

Claims

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Application Information

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IPC IPC(8): C08F226/06C08F222/24
Inventor 熊玉兵李凤焦振乾张静苗丛丛
Owner NORTHWEST NORMAL UNIVERSITY
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