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Bactericidal fluorescent ionic liquid and preparation method thereof

An ionic liquid and fluorescent technology, applied in the field of fluorescent materials, can solve the problems of complex compound structure, bacterial killing, and difficult preparation process, and achieve the effect of significant sterilization effect.

Inactive Publication Date: 2018-11-23
SUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Its fluorescent bioprobes are loaded with fluorescent compound nanoparticles, and the nanoparticles contain fluorescent compounds with aggregation-induced luminescent properties, wherein the fluorescent compounds contain one or more aggregation-induced luminescent fluorophores, but the compound structure is complex, and the preparation The process is not simple
The Chinese invention patent with the publication number CN107001927A discloses a method for synthesizing aggregation-induced emission (AIE) compounds for bacterial imaging. Although these can be used for imaging cells and bacteria without washing, they cannot kill bacteria

Method used

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  • Bactericidal fluorescent ionic liquid and preparation method thereof
  • Bactericidal fluorescent ionic liquid and preparation method thereof
  • Bactericidal fluorescent ionic liquid and preparation method thereof

Examples

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preparation example Construction

[0034] The preparation method of the above-mentioned bactericidal fluorescent ionic liquid comprises the following steps: dissolving the crown ether derivative and nitrogen-containing organic matter in a volatile solvent, stirring and reacting, evaporating in a vacuum to obtain a crude product, and then washing with diethyl ether for several times to obtain the product; The molar ratio of the crown ether derivative to nitrogen-containing organic matter is 1:4.05-4.1; the chemical structural formula of the crown ether derivative is Y is Cl, Br or I; The chemical structural formula of the nitrogen-containing organic compound is or The volatile solvent is chloroform, ethylene dichloride, methanol or ethanol. When X is BF 4 - 、PF 6 - and R 1 COO - In the case of one of them, it is also preferred to dissolve the product and place it in a hydroxide ion exchange resin for ion exchange, then react with the corresponding salts or acids, spin dry and wash with water for severa...

Embodiment 1

[0037] This embodiment provides a preparation method of a crown ether derivative (TPE-Br), specifically:

[0038] (a) Synthesis of (TPE-OMe): Zinc powder (2.7g) was added into anhydrous tetrahydrofuran (40ml) dissolved in 4,4-dimethoxybenzophenone (2.0g), and placed in an ice-water bath Cooling, under a nitrogen atmosphere, slowly add titanium tetrachloride (3.5ml) with a syringe, stir continuously, transfer to an oil bath at 66°C after the dropwise addition, and heat to reflux for 16 hours; add 10% potassium carbonate solution (mass fraction ) quenched the reaction to obtain a black-green oily liquid; purified by silica gel column chromatography to obtain TPE-OMe (0.97g; 42%); 1 H NMR (d 6 -DMSO,400MHz,δ):6.83-6.85(d,8H),6.67-6.69(d,8H),3.67(s,12H);

[0039] (b) Synthesis of (TPE-OH): Add TPE-OMe (2.0g) to anhydrous dichloromethane (40ml) solution and place it in an ice-water bath for cooling. Under nitrogen atmosphere, inject boron tribromide (1.7ml), and After stirrin...

Embodiment 2

[0042] This example provides a method for preparing a bactericidal fluorescent ionic liquid, comprising the following steps: dissolving TPE-Br and 1-methylimidazole in chloroform at a molar ratio of 1:4.05, stirring at room temperature for 24 hours; then evaporating in vacuo mixture to obtain a crude product, which was washed three times with ether to remove residual 1-methylimidazole to obtain a yellow viscous liquid (i.e. TPE-C 1 Im), 1 H NMR (400MHz, d 6 -DMSO,δ):9.118(s,4H),7.774(s,4H),7.708(s,4H),6.848-6.814(d,8H),6.695-6.643(d,8H),4.235-4.170(m ,8H),3.929-3.878(m,8H),3.604-3.542(m,12H),1.827-1.739(m,8H)(eg Figure 10 ), its fluorescence intensity comparison in poor solvent water and good solvent ethanol is as figure 1 shown.

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Abstract

The invention relates to bactericidal fluorescent ionic liquid and a preparation method thereof. The bactericidal fluorescent ionic liquid is a mixture formed by one or more of the chemical structuralformulas in the specification, wherein n is an integer of 0-6, X is one of Cl, Br, I, BF4, PF6<-> and R1COO<->, and R and R1 are independent of each other and each is an alkyl group with carbon atomnumber being 1 to 8. The bactericidal fluorescent ionic liquid has significant bactericidal effect and aggregation-induced emission feature, and can be used for bacterial imaging without washing bacteria imaging; by adjusting alkyl chains of different lengths, the antibacterial properties can be adjusted, and the different fluorescence phenomena can be adjusted.

Description

technical field [0001] The invention belongs to the technical field of fluorescent materials, and relates to a bactericidal fluorescent ionic liquid, in particular to a bactericidal fluorescent ionic liquid and a preparation method thereof. Background technique [0002] In recent years, with the emergence of drug-resistant bacteria, the development of antibacterial active materials has attracted great attention from all walks of life in modern times. At present, the most researched and most widely used antibacterial agents are cationic compounds. Cationic antibacterial agents have been widely studied due to their high efficiency, broad spectrum, high biocompatibility, and low toxicity, such as quaternary ammonium salts, pyridinium salts, and imidazolium salts . Bioimaging, because of its high sensitivity, high visibility, and strong adjustability, has become a powerful tool in today's biological research. Among them, fluorescent bioimaging provides a simple and unique metho...

Claims

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Application Information

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IPC IPC(8): A01N43/50A01N43/36C07D233/60C07D295/088C09K11/06A01P1/00
CPCA01N43/36A01N43/50C07D233/60C07D295/088C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044
Inventor 郭江娜严锋史洁
Owner SUZHOU UNIV
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