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Compound containing rhodamine groups and benzofurazan groups and preparation method and application thereof

A technology for benzofurazan and compounds, which is applied in the fields of preparation and application of compounds containing rhodamine groups and benzofurazan groups, and achieves the effects of high accuracy and convenient operation

Inactive Publication Date: 2015-09-30
SOUTH CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Since traditional fluorescent probes can only detect a specific metal ion, it is of great practical significance and application prospect to develop a fluorescent probe that can selectively recognize multiple metal ions, especially heavy metal ions.

Method used

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  • Compound containing rhodamine groups and benzofurazan groups and preparation method and application thereof
  • Compound containing rhodamine groups and benzofurazan groups and preparation method and application thereof
  • Compound containing rhodamine groups and benzofurazan groups and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0056] Synthesis of nitrogen-(7-nitrobenzofurazan)-rhodamine B-acyldiethylenetriamine

[0057]

[0058] (I)

[0059] The synthetic route of nitrogen-(7-nitrobenzofurazan)-rhodamine B acid diethylenetriamine is shown in formula (I), and the specific synthetic steps are as follows:

[0060] (1) Synthesis of rhodamine B-acyl diethylenetriamine

[0061] Dissolve Rhodamine B (0.5 g 1 mM) in a round bottom flask filled with 20 mL of ethanol, stir at room temperature for 5 minutes, after Rhodamine B is completely dissolved, slowly add 3 mL of diethylenetriamine dropwise, and reflux at 70°C for 12 hours , until the solution changed from red to orange-yellow. Remove the solvent, add dichloromethane to dissolve, and wash with distilled water until the water phase is colorless, collect, dry the organic layer and spin dry to obtain the product, which is directly used for the next reaction without further purification. Preliminary separation and purification

[0062] (2) Synthesis...

Embodiment 2

[0066] Titrate the concentrated solution of mercury ions to a concentration of 1.0 × 10 -5 In the ethanol solution of nitrogen-(7-nitrobenzofurazan)-rhodamine B-acyldiethylenetriamine of mol / L, the concentration of mercury ions is respectively 0.0, 0.5, 1.0, 1.5, 2.0, 3.0, 4.0, 5.0, 7.0, 10.0, 12.5.0, 15.0, 20.0, 25.0, 30.0, 40.0, 50.0, 60.0, 80.0, 100.0 μM (× 10 -6 mol / L), and respectively detect their fluorescence intensities at the excitation wavelength of 525 nm, draw the fluorescence spectrum diagram, the obtained fluorescence spectrum diagram is as follows image 3 In (A) shown.

[0067] Titrate the concentrated solution of iron ions to a concentration of 1.0 × 10 -5 mol / L of nitrogen-(7-nitrobenzofurazan)-rhodamine B-acyldiethylenetriamine contains 30% ethanol in the aqueous ethanol solution so that the concentration of iron ions is respectively 0.0, 5.0, 10.0, 15.0, 20.0, 25.0, 27.0, 30.0, 35.0, 40.0, 50.0, 60.0 , 70.0, 80.0, 90.0, 100.0, 115.0 μM (× 10 -6 mol / ...

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Abstract

The invention discloses a compound containing rhodamine groups and benzofurazan groups and a preparation method and application thereof. The structural formula of the compound is as shown in the specification. The preparation method comprises the following steps: (1) enabling rhodamine B and diethylenetriamine to fully react in a solvent, removing the solvent, and performing preliminary separation and purification; (2) enabling rhodamine B acyl diethylenetriamine and 4-chloro-7-nitrobenzofuroxan to fully react in a solvent, monitoring the reaction process by virtue of TLC, and performing column elution after the reaction is ended, thereby obtaining the product. The method for detecting the concentration of mercury ions or iron ions comprises the following steps: (1) making a standard curve; (2) detecting and recording; and (3) calculating. The invention further discloses an application of the compound serving as an iron ion fluorescence probe or a mercury ion fluorescence probe. The invention also discloses an application of the compound serving as an iron ion specific fluorescence probe or a mercury ion specific fluorescence probe. The compound disclosed by the invention can serve as a specific fluorescence probe for mercury ions or iron ions, is used for detecting mercury ions or iron ions in the solution and is high in accuracy.

Description

technical field [0001] The invention relates to a compound containing a rhodamine group and a benzofurazan group, a preparation method and an application. Background technique [0002] Mercury is a highly toxic heavy metal. Mercury pollution is also a common heavy metal pollution. Once mercury ions are absorbed by the human body, it will interfere with some metabolic processes involving amino acids, proteins and enzymes. Once mercury elements / mercury ions enter the ocean, Bacteria can convert inorganic mercury into organic mercury (such as methylmercury), and continuously accumulate in organisms in the ocean, especially edible fish, and finally enter the human body through the food chain. Methylmercury can poison the nerves, It can lead to perception, behavior disorder and nerve damage, causing multi-system damage to the body mainly including neurotoxicity and renal toxicity, and then seriously endangering human health. The U.S. Environmental Protection Agency (EPA) clearly...

Claims

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Application Information

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IPC IPC(8): G01N21/64
Inventor 马立军李煦田殷悦邓俊杰陈嘉韵唐健陈志杨丽庭
Owner SOUTH CHINA NORMAL UNIVERSITY
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