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A fluorescent probe for detecting zinc ions and its preparation method and application

A fluorescent probe, zinc ion technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as impaired immunity and poisoning, and achieve low ion interference, good water solubility, and low toxicity. Effect

Inactive Publication Date: 2018-11-02
FUJIAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, excessive zinc intake can lead to poisoning, abdominal pain, vomiting and other symptoms of acute zinc poisoning, as well as impairment of kidney and liver function immunity.

Method used

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  • A fluorescent probe for detecting zinc ions and its preparation method and application
  • A fluorescent probe for detecting zinc ions and its preparation method and application
  • A fluorescent probe for detecting zinc ions and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] 1. The synthetic steps of 4-(2-hydroxyethoxy) benzaldehyde (hereinafter referred to as compound 1):

[0038] Add 12.2g (0.1mol) of p-hydroxybenzaldehyde and 6.9g of potassium carbonate (5mmol) to a 250mL three-necked flask equipped with 150mL of acetonitrile, stir evenly, then add 9.66g (0.72mol) of chloroethanol, electromagnetically stir, and heat Reflux for 8 hours, TLC detects that the raw material completely disappears, and the reaction is stopped. Cool to room temperature, separate the organic layer, wash the organic layer with sodium hydroxide solution until there is no p-hydroxybenzaldehyde, separate the organic layer, dry over magnesium sulfate, filter, and concentrate the filtrate to obtain 14.9 g of compound 1.

[0039]

[0040] 2. Synthesis steps of compound 2:

[0041] Add 1.0 g (2.6 mmol) of compound 1 into a three-necked flask filled with 50 mL of toluene, stir well, and then add 1.14 g (10 mmol) of glutaric anhydride. Under the condition of 100° C., ...

Embodiment 2

[0047] 1, the synthetic steps of 4-(2-hydroxyethoxy) benzaldehyde (hereinafter referred to as compound 1):

[0048] Add 0.1mol of p-hydroxybenzaldehyde and 5mmol of potassium carbonate to a 250mL three-necked flask filled with 150mL of acetonitrile, stir evenly, then add 0.1mol of chloroethanol, stir electromagnetically, heat and reflux for 20 hours, TLC detects that the raw materials completely disappear, stop reaction. Cool to room temperature, separate the organic layer, wash the organic layer with sodium hydroxide solution until there is no p-hydroxybenzaldehyde, separate the organic layer, dry over magnesium sulfate, filter, and concentrate the filtrate to obtain compound 1.

[0049]

[0050] 2. Synthesis steps of compound 2:

[0051] Into a three-neck flask filled with 50 mL of toluene, add 2.6 mmol of compound 1, stir well, and then add 2.6 mmol of glutaric anhydride. Under the condition of 100° C., electromagnetic stirring, heating and reflux for 8 hours, TLC dete...

Embodiment 3

[0056] 1. The synthetic steps of 4-(2-hydroxyethoxy) benzaldehyde (hereinafter referred to as compound 1):

[0057] Add 0.1mol of p-hydroxybenzaldehyde and 5mmol of potassium carbonate to a 250mL three-necked flask filled with 150mL of acetonitrile, stir evenly, then add 1mol of chloroethanol, stir electromagnetically, heat and reflux for 20 hours, TLC detects that the raw materials completely disappear, stop the reaction . Cool to room temperature, separate the organic layer, wash the organic layer with sodium hydroxide solution until there is no p-hydroxybenzaldehyde, separate the organic layer, dry over magnesium sulfate, filter, and concentrate the filtrate to obtain compound 1.

[0058]

[0059] 2. Synthesis steps of compound 2:

[0060] Into a three-neck flask filled with 50 mL of toluene, add 2.6 mmol of compound 1, stir well, and then add 52 mmol of glutaric anhydride. Under the condition of 100° C., with electromagnetic stirring, heated to reflux for 40 hours, TL...

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Abstract

The invention relates to a fluorescence probe for detecting zinc ions, and a preparation method and an application thereof. The fluorescence probe is a high-fluorescence dimethylpyrrole BODIPY. The fluorescence probe is chemically named as 8-[4-(1-oxocarboxylpentyloxy-ethoxy)phenyl]-4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-dipyrrole (called carboxyl BODIPY for short). The fluorescence probe is obtained through a condensation reaction of p-hydroxybenzaldehyde and chloroethanol, a condensation reaction of the p-hydroxybenzaldehyde and glutaric anhydride, and a BODIPY one-pot reaction. The carboxyl BODIPY is pale yellow in a solution and has very strong fluorescence emission at 507 nm, the fluorescence quantum yield reaches 0.96, the carboxyl BODIPY has good water solubility and low toxicity, and can highly-sensitively identify zinc ions, the lowest detection limit reaches 3.64 [mu]M, the interference of other ions is small, and the carboxyl BODIPY is an ideal zinc ion rapid detection sensor.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and analytical chemistry, and in particular relates to a fluorescent probe for detecting zinc ions, a preparation method and application thereof. Background technique [0002] Due to the high selectivity and sensitivity of fluorescent probes, they have been widely used in the detection of cations and anions. These fluorescent probes are easily modified to suit different testing environments and test objects. At present, dimethylpyrrole BODIPY has become one of the attractive fluorescent probes. This BODIPY fluorescent probe generally has strong photochemical stability, high fluorescence intensity, and strong environmental adaptability, showing a good application prospect. [0003] Zinc ions play an important role in the activity of enzymes in the human body. It not only participates in the differentiation of epithelial tissue, but also participates in the transport and storage of metal...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06C09K2211/1055G01N21/643G01N2021/6432
Inventor 严祯曦杨发福郭红玉邱家斌方小婷林梁斌
Owner FUJIAN NORMAL UNIV
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