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Symmetrical double-rhodamine B fluorescent probe for detecting mercury ion and preparation method of fluorescent probe

A fluorescent probe, mercury ion technology, used in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., to achieve high selectivity and high selectivity

Inactive Publication Date: 2013-08-21
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the reported mercury ion fluorescent probes based on rhodamine B can only be used in organic solvent media or aqueous solutions containing more than 40% organic solvents (Dalton Trans., 2011, 40, 12578-12583; Dyes Pigm., 2013, 98, 42-50)

Method used

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  • Symmetrical double-rhodamine B fluorescent probe for detecting mercury ion and preparation method of fluorescent probe
  • Symmetrical double-rhodamine B fluorescent probe for detecting mercury ion and preparation method of fluorescent probe
  • Symmetrical double-rhodamine B fluorescent probe for detecting mercury ion and preparation method of fluorescent probe

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Experimental program
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Effect test

Embodiment 1

[0026] (1) Synthesis of rhodamine B acid chloride: Rhodamine B (0.49g) and phosphorus oxychloride (0.5ml) were refluxed in 30ml of dichloroethane for 16 hours, and the solvent was removed by rotary evaporation. The obtained acid chloride was used in the next reaction .

[0027] (2) Synthesis of rhodamine B-acyl-2-bromoethylamine: the obtained rhodamine B-acyl chloride (0.5 g) and 2-bromoethylamine (0.3 g) were dissolved in 30 mL of acetonitrile, and stirred overnight at room temperature for reaction. Solvent was removed using a rotary evaporator. The obtained crude product was purified by silica gel column chromatography, and the eluting solvent was n-hexane and ethyl acetate in a volume ratio of 1:1.

[0028] (3) Synthesis of the symmetrical bisrhodamine B fluorescent probe RBSRB: Reflux the obtained Rhodamine B-2-bromoethylamine (0.1g) and Na2S (0.5g) in 20ml ethanol for 6h, and remove the solvent with a rotary evaporator , purified by silica gel column chromatography, the...

Embodiment 2

[0032] The selectivity of the fluorescent probe RBSRB for the fluorescence detection of mercury ions:

[0033] Tris-HCl buffer solution with pH=7.4 was used to control the experimental conditions to meet the physiological environmental conditions.

[0034] Add 0.1ml ethanol solution (1mM) of fluorescent probe RBSRB, 8.0ml Tris-HCl buffer solution, 0.3ml aqueous solution of metal ions to be tested to different 10ml colorimetric tubes (the concentration of mercury ions is 1mM, and the concentration of other metal ions Both are 10mM), and dilute to 10ml with Tris-HCl buffer solution. After constant volume, the concentration of fluorescent probe is 10 M, and the concentration of mercury ion is M, and the concentration of other metal ions was 300 M. Transfer 3ml of the working solution to a 1cm fluorescence cuvette to measure the fluorescence spectrum, the excitation wavelength is 510nm. In the blank experiment, no metal ions were added to the above solution. Selective detecti...

Embodiment 3

[0036] Quantitative fluorescence detection of mercury ions by fluorescent probe RBSRB:

[0037] Add 0.1ml ethanol solution (1mM) of fluorescent probe 1, 8.0ml Tris-HCl buffer solution, 0-1.0ml different volumes of 1mM mercury ion aqueous solution to different 10ml colorimetric tubes, and use Tris-HCl buffer solution to make up the volume to 10ml. After constant volume, the concentration of fluorescent probe is M, the mercury ion concentration is 0-100 M. Transfer 3ml of the working solution to a 1cm fluorescence cuvette to record the fluorescence spectrum and read and record the fluorescence intensity at 588nm. The fluorescence intensity and the corresponding mercury ion concentration data were input into the software Origin8 for fitting, and a linear working curve was obtained in the range of mercury ion concentration 0-30 M, and the linear regression constant was 0.9957, which indicated that the probe could quantitatively detect the concentration of mercury ions. The cha...

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Abstract

The invention relates to a symmetrical double-rhodamine B fluorescent probe for detecting a mercury ion and a preparation method of the fluorescent probe. The structural formula of the symmetrical double-rhodamine B fluorescent probe RBSRB (rhodamine B-symmetrical-rhodamine B) is as shown in the specification. The preparation method comprises the following steps: adding rhodamine B and phosphorus oxychloride into a solvent for reflux reaction for 20-24h at 85-90 DEG C, obtaining rhodamine B acyl chloride, dissolving rhodamine B acyl chloride and 2-bromine ethylamine in the solvent, stirring for reaction for one night at room temperature, purifying to obtain rhodamine B acyl-2-bromine ethylamine, adding rhodamine B acyl-2-bromine ethylamine and sodium sulfide into the solvent for reflux reaction for 5-8h at 80-85 DEG C, and purifying to obtain the fluorescent probe. The fluorescent probe is symmetrical double-rhodamine B amide connected by a sulphur atom; only alcohol under 1% is introduced as a cosolvent during an experiment; the fluorescent probe is high in selectivity, and has high selectivity to the mercury ion; other common ions do not interfere with the fluorescent probe obviously; and the fluorescent probe has an application prospect in bioluminescence imaging.

Description

technical field [0001] The invention belongs to the field of fluorescent probes and preparation thereof, in particular to a symmetrical bisrhodamine B fluorescent probe for detecting mercury ions and a preparation method thereof. Background technique [0002] Toxic heavy metal pollution represented by heavy metal ions such as mercury, lead, and cadmium is one of the major pollution sources facing environmental pollution. As a typical toxic heavy metal, mercury ions can cause permanent damage to the nervous system of organisms. Therefore, it is of great significance to develop simple, rapid and sensitive detection methods that can be applied to the detection of mercury ions in physiological environments. The fluorescent probe method has attracted much attention due to its simplicity, rapidity, high sensitivity, good selectivity, and ease of automation and visualization. In recent years, there have been many reports on the detection of mercury ions based on small molecule flu...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D519/00G01N21/64
Inventor 张煊黄小娟
Owner DONGHUA UNIV
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