Fluorescence probe for detecting cyanide ions and preparation method and application of fluorescence probe

A fluorescent probe and cyanide ion technology, applied in the field of fluorescent probes, can solve the problems of difficult to identify anions, non-repeatable identification, complex probe synthesis, etc., and achieve high selectivity and sensitivity, fast response speed, and good application. Foreground effect

Active Publication Date: 2019-09-06
SHANGHAI INST OF TECH
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  • Abstract
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Problems solved by technology

At present, people have designed and synthesized many anion fluorescent probes with potential application value, but most of the probes are complicated to synthesize, high in cost, cannot be reproducibly identified, and it is difficult to identify anions in aqueous solution.

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  • Fluorescence probe for detecting cyanide ions and preparation method and application of fluorescence probe
  • Fluorescence probe for detecting cyanide ions and preparation method and application of fluorescence probe
  • Fluorescence probe for detecting cyanide ions and preparation method and application of fluorescence probe

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Embodiment 1

[0054] 1. Synthesis of BODIPY 1 molecule, a fluorescent probe for detecting cyanide ions

[0055] The synthesis of the fluorescent probe molecule for detecting cyanide ion in the present invention is obtained by using pyrrole and benzaldehyde as raw materials through condensation, bromination, oxidation, fluoroboration, and nucleophilic substitution reaction with benzyl nitrile.

[0056] (1) Synthesis of 5-(4-methylphenyl) dipyrromethane:

[0057] Benzaldehyde (5.00g, 47.20mmol), pyrrole (20mL, 289mmol) and anhydrous CH 2 Cl 2 (250 mL) was added into a 500 mL round-bottomed flask, which was replaced with a nitrogen system, then trifluoroacetic acid (200 mg, 2.60 mmol) was added to the mixture, and the reaction was stirred at room temperature for 2 h. After the reaction was complete, it was washed with saturated sodium bicarbonate solution. The organic layer was dried over anhydrous sodium sulfate, the filtrate was collected, concentrated, and purified by silica gel column c...

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Abstract

The invention relates to a fluorescence probe for detecting cyanide ions and a preparation method and application of the fluorescence probe. The fluorescence probe is a cyanide ion fluorescence probetaking boron dipyrromethene (BODIPY) as a fluorescence signal group and taking an activated CH group in a benzyl cyanide group as a recognition site, and the probe is obtained through a nucleophilic substitution reaction of 3,5-dibromo8-phenyl boron fluoride dipyrrole and benzyl cyanide. Through the research of an ultraviolet absorption and a fluorescence emission spectroscopy method, it is foundthat the probe can identify the cyanide ions singly, the lowest detectable limit in a 70% aqueous solution can reach 148 nM, and the recognition process is not disturbed by other anions. Compared withthe prior art, the fluorescence probe has the advantages that the synthesis method is simple, the raw materials are easy to obtain, the cost is lower, the selectivity to the cyanide ions is good, thesensitivity is high, reversibility is provided, the detection can be performed in the aqueous solution, and therefore the fluorescence probe has a good application prospect in the detection of the cyanide ions.

Description

technical field [0001] The invention relates to the field of fluorescent probes, in particular to a fluorescent probe for detecting cyanide ions, a preparation method and application thereof. Background technique [0002] Anions widely exist in nature and organisms, and play an important role in environmental science, clinical medicine, chemistry, biology and other fields. Among the many anions, cyanide ion has extremely high toxicity to the human body. The poisoning mechanism is that the cyanide ion can complex with the ferric ion of cytochrome oxidase, resulting in the loss of the ability of the ferric iron to transfer electrons, making the respiratory chain Interruption, eventually leading to human death due to lack of oxygen. In addition, cyanide ion also plays a very important role in synthetic fibers, leather products, metallurgical industry and electroplating technology, but the extensive use of cyanide in industrial production will inevitably cause harm to organisms...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06C09K2211/1007C09K2211/1029C09K2211/1055G01N21/643G01N2021/6432
Inventor 刘传祥付超李喆垚饶才辉陈璐朱婷婷
Owner SHANGHAI INST OF TECH
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