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Synthesis method and application method of benzothiazole di-Schiff base fluorescent molecular probe for detection of iron ions

A technology of benzothiazole double Schiff base and fluorescent molecular probe, which is applied in the fields of fluorescence/phosphorescence, chemical instruments and methods, and material analysis through optical means, and can solve poor selectivity and sensitivity, and poor water solubility of fluorescent probes , easy to be affected by pH and other problems, to achieve the effect of simple steps, strong anti-interference ability, and simple and easy-to-obtain raw materials

Inactive Publication Date: 2019-09-13
UNIV OF SCI & TECH LIAONING
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Problems solved by technology

[0006] In order to overcome the deficiencies in the prior art, the object of the invention is to provide a kind of synthesis and the use method of the benzothiazole double Schiff base fluorescent probe that is used for iron ion detection, solve existing identification Fe 3+ The fluorescent probes have poor water solubility, are easily affected by pH, and have poor selectivity and sensitivity.

Method used

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  • Synthesis method and application method of benzothiazole di-Schiff base fluorescent molecular probe for detection of iron ions
  • Synthesis method and application method of benzothiazole di-Schiff base fluorescent molecular probe for detection of iron ions
  • Synthesis method and application method of benzothiazole di-Schiff base fluorescent molecular probe for detection of iron ions

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preparation example Construction

[0035] The synthetic method specifically comprises the following steps:

[0036] 1) Add benzothiazole-2-carbaldehyde to 2-hydroxy-1-naphthalene hydrazine in a molar ratio of 1:(1~2) into an acidic solvent, heat under reflux to 75-80°C, react for 5~7 hours, and pump while it is hot Filter to obtain the reaction mixture;

[0037] 2) Recrystallize the reaction mixture using a mixed solvent of acetone and water, and precipitate a large amount of solid after cooling; filter and collect the filter cake to obtain a benzothiazole bis-Schiff base fluorescent molecular probe (BP) for iron ion detection.

[0038] Wherein, the acidic solvent described in step 1) is glacial acetic acid, or ethanol solvent of concentrated sulfuric acid or concentrated hydrochloric acid, and the concentration of concentrated sulfuric acid or concentrated hydrochloric acid in the ethanol solvent of concentrated sulfuric acid or concentrated hydrochloric acid is 5%-10%. The volume ratio of acetone and water i...

Embodiment 1

[0044] Synthetic method of benzothiazole double Schiff base fluorescent molecular probe for iron ion detection:

[0045] 1) Add 163 mg (1 mmol) of benzothiazole-2-carbaldehyde and 172 mg (1 mmol) of 2-hydroxy-1-naphthylhydrazine into 15 mL of glacial acetic acid, reflux for 5 to 7 hours, and suction filter while hot to obtain a reaction mixture;

[0046] 2) Recrystallize the filter cake with acetone and water to obtain a fluorescent molecular probe, which is a benzothiazole double Schiff base ratio fluorescent molecular probe for iron ion detection. The calculated yield was 71%.

[0047] The mass spectrometry and elemental analysis of the benzothiazole double-Schiff base ratio fluorescent molecular probe used for the detection of iron ions prepared in this example and its detection in deuterium-substituted dimethyl sulfoxide DMSO solvent 1 H NMR spectral data are as follows:

[0048] 1 H NMR(500MHz,DMSO)δ12.18(s,1H),8.88(s,1H),8.64(s,1H),7.88(t,J=9.3Hz,2H),7.76(d,J=7.4Hz ,...

Embodiment 2

[0061] The preparation method of the benzothiazole bis-Schiff base ratio fluorescent molecular probe for iron ion detection is as follows:

[0062] 1. According to the molar ratio of benzothiazole-2-formaldehyde and 2-hydroxyl-1-naphthalene hydrazine as 1:(1~2), add benzothiazole-2-formaldehyde and 2-hydroxyl-1-naphthalene hydrazine to In the ethanol solvent of concentrated sulfuric acid, reflux for 5 to 7 hours, and suction filter while it is hot to obtain the reaction mixture;

[0063] 2. Recrystallize the reaction mixture with a mixed solvent of acetone and water, and precipitate a large amount of solids after cooling; filter and collect the filter cake to obtain the fluorescent molecular probe BP, which is the ratio of benzothiazole bis-Schiff base for iron ion detection Fluorescent Molecular Probes. The calculated yield was 74%.

[0064] The mass spectrometry and elemental analysis of the benzothiazole double Schiff base ratio fluorescent molecular probe for the detecti...

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Abstract

The invention relates to a synthesis method and application method of a benzothiazole di-Schiff base fluorescent molecular probe for detection of iron ions. The fluorescent molecular probe is obtainedthrough condensation of benzothiazole-2-formaldehyde and 2-hydroxy-1-naphthylhydrazine, and the fluorescent molecular probe is dissolved in a mixed liquid of dimethyl sulfoxide and an HEPES buffer solution so as to obtain a fluorescent molecular probe solution, wherein the pH value of the HEPES buffer solution is 6-8, and the volume ratio of methyl sulfoxide to the HEPES buffer solution in the mixed liquid is 3:7, and the concentration of the fluorescent molecular probe in the mixed liquid of 3:7 is 7-10 [mu]mol / L; a to-be-detected sample of 20 [mu]mol / L is added to the taken fluorescent molecular probe solution, and even mixing is performed so as to obtain a sample solution. The synthesis method and application method have the advantages that high-selectivity identification of Fe<3+> inthe water environment system can be realized, no interference is caused by other metal ions in the water solution, and a high anti-interference ability is achieved.

Description

technical field [0001] The present invention relates to Fe 3+ The invention relates to the synthesis and application of a fluorescent molecular probe for detection, in particular to a synthesis and application method of a benzothiazole double Schiff base fluorescent molecular probe for iron ion detection. Background technique [0002] Iron is not only an element that widely exists in nature, but also one of the important trace elements in living organisms. It plays a key role in many physiological processes. It can not only transport nutrients and oxygen, but also has a very close relationship with the hematopoietic function of the human body. Relationship. It participates in the synthesis of various active enzymes and hemoglobin in cells, and promotes cell growth and metabolism. When the concentration of iron ions in the body is too high or too low, it will disturb the normal activities of the life system and poison the cells, which will lead to metabolic disorders and in...

Claims

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Application Information

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IPC IPC(8): C07D277/64C09K11/06G01N21/64
CPCC07D277/64C09K11/06G01N21/643C09K2211/1011C09K2211/1037G01N2021/6432
Inventor 张立华高妍李庚辉
Owner UNIV OF SCI & TECH LIAONING
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