Preparation method of phenyl hydrazino thioformate-rhodamine fluorescent molecule, prepared fluorescent molecule and application of fluorescent molecule

A technology of hydrazine thiocarboxylate and chloromethyl thiophenyl ester is applied in the field of fluorescence sensors, which can solve problems such as selectivity influence, and achieve the effects of simple preparation method, good stability, good selectivity and sensitivity

Active Publication Date: 2022-01-04
CHAOHU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] At present, there have been some studies on the identification of Sn 2+ Fluorescent probes are reported, as the patent disclosure of CN105907387A discloses a method of utilizing rhodamine fluorescent probes to detect stannous ions, but these probes are all based on Sn 2+ Designed for complexation reactions with fluorescent probes whose selectivity may be affected by other related analytes

Method used

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  • Preparation method of phenyl hydrazino thioformate-rhodamine fluorescent molecule, prepared fluorescent molecule and application of fluorescent molecule
  • Preparation method of phenyl hydrazino thioformate-rhodamine fluorescent molecule, prepared fluorescent molecule and application of fluorescent molecule
  • Preparation method of phenyl hydrazino thioformate-rhodamine fluorescent molecule, prepared fluorescent molecule and application of fluorescent molecule

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Embodiment 1

[0042] Preparation of Phenylhydrazinothiocarbamate-Rhodamine Fluorescent Molecule CK

[0043] Rhodamine hydrazide was prepared according to the literature method (Chem. Commun., 2015, 51, 1697-1700). Under nitrogen protection, rhodamine B and hydrazine hydrate were refluxed in ethanol for 8 hours to obtain rhodamine hydrazide. The specific structural formula is:

[0044]

[0045] Phenylhydrazinothioformate-rhodamine fluorescent molecule CK is obtained by thioacylation reaction of rhodamine hydrazide and chloromethylthiophenyl ester. The specific synthesis method is as follows:

[0046] At room temperature, dissolve rhodamine hydrazide (456mg, 1.0mmol) in 10.0ml of dichloromethane, stir until the rhodamine hydrazide dissolves, then slowly add chloromethylthiophenyl ester (150μL, 1.1mmol) of dichloromethane solution, after the above mixed solution was reacted at room temperature for 16h, the organic solvent was removed under reduced pressure, and the crude product was separ...

Embodiment 2

[0055] Phenylhydrazinothiocarbamate-rhodamine fluorescent molecule CK on Sn 2+ Fluorescent response of

[0056] Method: Add the probe solution of phenylhydrazinothiocarbamate-rhodamine fluorescent molecule CK (water / ethanol=4:1, v / v) with a concentration of 10 μM into the cuvette, and scan the fluorescence spectrum , and then dropwise added 0-28 equivalents of Sn to the probe solution 2+ After the solution was thoroughly shaken and mixed at room temperature, the fluorescence spectrum scanning was carried out respectively. Among them, the fluorescence excitation wavelength is set to 500nm, and the slit: 10 / 10nm.

[0057] the result shows: figure 1 and figure 2 Add different concentrations of Sn to the hydrazinothiocarbamate-rhodamine fluorescent molecule CK solution 2+ Fluorescence spectra and linear relationship diagrams. Such as figure 1 and figure 2 As shown, the phenylhydrazinothiocarbamate-rhodamine fluorescent molecule CK itself has almost no fluorescence, with ...

Embodiment 3

[0059] Phenylhydrazinothiocarbamate-rhodamine fluorescent molecule CK on Sn 2+ response time

[0060] Method: Take the probe solution of phenylhydrazinothiocarbamate-rhodamine fluorescent molecule CK (water / ethanol=4:1, v / v) with a concentration of 10 μM and 20 equivalents of Sn 2+ The solution is added into a cuvette, detected on a fluorescence spectrophotometer, and scanned at intervals until the fluorescence intensity is basically stable. Among them, the fluorescence excitation wavelength is set to 500nm, and the slit: 10 / 10nm.

[0061] the result shows: image 3 Phenylhydrazinothiocarbamate-rhodamine fluorescent molecule CK in water / ethanol (volume ratio 4:1) and Sn 2+ Time-dependent fluorescence spectra of the reactions. Such as image 3 As shown, the effect of phenylhydrazinothiocarbamate-rhodamine fluorescent molecule CK on Sn 2+ The response speed is very fast, and the response reaches a balance within 20s and completes the Sn 2+ detection.

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Abstract

The invention discloses a preparation method of a phenyl hydrazino thioformate-rhodamine fluorescent molecule, and relates to the technical field of fluorescent sensors, wherein the preparation method comprises the following steps: dissolving rhodamine hydrazide and chloromethyl thiophenyl ester in an organic solvent, reacting for a period of time at a certain temperature, removing the organic solvent under reduced pressure, and separating and purifying to obtain a product. The invention also provides the phenyl hydrazino thioformate-rhodamine fluorescent molecule prepared by adopting the preparation method and the application of the phenyl hydrazino thioformate-rhodamine fluorescent molecule. The phenyl hydrazino thioformate-rhodamine fluorescent molecule has the beneficial effects that the phenyl hydrazino thioformate-rhodamine fluorescent molecule is not reported in the prior art, and the fluorescent molecule disclosed by the invention can be used for inducing a thiobenzene ester group in a structure to be desulfurized to form a CD molecule and inducing a closed-loop-open-loop structure of rhodamine to be interconverted by utilizing the thiophilic property of Sn<2+>, so that the fluorescent property of the molecule is sensitively regulated and controlled, the fluorescent molecule shows good selectivity and sensitivity on Sn<2+> recognition, and is not interfered by other metal ions in the detection process.

Description

technical field [0001] The invention relates to the technical field of fluorescent sensors, in particular to a preparation method of phenylhydrazinothiocarbamate-rhodamine fluorescent molecules, the prepared fluorescent molecules and applications thereof. Background technique [0002] As a typical heavy metal, tin is an essential trace element for human growth, mainly found in liver, brain, adrenal gland and other tissues. Reports have shown that tin deficiency can lead to hearing loss, poor physical development, and dental disease, but excessive accumulation of tin in the human body can pose fatal risks to human health, such as neurological diseases such as Alzheimer's disease and Menkes syndrome and Lung disease, stomach disease, etc. SnCl 2 Is a mild Lewis acid widely used as an effective reducing agent or catalyst in the synthesis of organic compounds and in the preparation of various everyday products such as dyes, perfumes and food. With the development of industry,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K11/06C09K11/02G01N21/64D01F1/10D01F6/52D04H1/728
CPCC07D491/107C09K11/06C09K11/025G01N21/6428D01F6/52D01F1/10D04H1/728C09K2211/1033
Inventor 孔亚琼曹多军秦国旭吴凤义
Owner CHAOHU UNIV
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