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Reactive rhodamine fluorescent probe for detecting mercury ions, and preparation method thereof

A fluorescent probe and reaction-type technology, applied in the field of fluorescent probe materials and their preparation, can solve the problem of less mercury ion fluorescent probes, and achieve the effects of good water solubility, simple preparation method and high selectivity

Inactive Publication Date: 2014-05-28
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reactive rhodamine fluorescent probes reported to detect mercury ions are generally realized through the desulfurization reaction of mercury ions, while there are fewer mercury ion fluorescent probes based on other reactions (Chem. Rev., 2013, 113, 192-270)

Method used

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  • Reactive rhodamine fluorescent probe for detecting mercury ions, and preparation method thereof
  • Reactive rhodamine fluorescent probe for detecting mercury ions, and preparation method thereof
  • Reactive rhodamine fluorescent probe for detecting mercury ions, and preparation method thereof

Examples

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Effect test

Embodiment 1

[0027] (1) Synthesis of rhodamine B hydrazide: Rhodamine B (5.0g) and hydrazine hydrate (5.0ml) were refluxed in 30ml ethanol for 2 hours, the solvent was removed by rotary evaporation, water was added and 1M dilute hydrochloric acid was used to adjust to acidic (pH =2), dissolve all the solid residues, and then use 1M sodium hydroxide solution to adjust to weak alkalinity (pH=9-10); filter the precipitated precipitate, wash with water, purify, and dry in vacuo to obtain 4.0g rhodamine B yl Hydrazine, yield 78%. ESI-MS(M+H) + :m / z calcd457.3;found457.4. (2) Synthesis of reactive fluorescent probe RBHA: rhodamine B hydrazide (1.0 g) and glyoxylic acid (0.4 g) were dissolved in 15 mL of methanol, and stirred for 10 hours at room temperature under nitrogen protection. The precipitate was filtered and washed with methanol three times, and dried in vacuum to obtain 0.85 g of the target product RBHA with a yield of 76%.

[0028] 1 H NMR (400MHz, DMSO-d 6 ),d(ppm):1.08(t,J=8.0Hz...

Embodiment 2

[0031] The selectivity of the fluorescent probe RBHA for the fluorescence detection of mercury ions:

[0032] Tris-HCl buffer solution with pH=7.4 was used to control the experimental conditions.

[0033] Add 0.1ml ethanol solution (1mM) of fluorescent probe RBAH and 2ml aqueous solution of metal ions to be tested (both metal ion concentration is 1mM) to different 10ml colorimetric tubes respectively, dilute to 10ml with Tris-HCl buffer solution, place 1 hour. Transfer 3ml of the working solution to a 1cm fluorescence cuvette to measure the fluorescence spectrum, the excitation wavelength is 520nm. In the blank experiment, no metal ions were added to the above solution. Selective detection of mercury ions such as figure 2 shown (inset is a photograph of fluorescence emission). Visible fluorescence is significantly enhanced only in the presence of mercury ions, indicating the high selectivity of the fluorescent probe RBAH involved in the present invention to mercury ions. ...

Embodiment 3

[0035] Quantitative fluorescent detection of mercury ions by fluorescent probe RBAH:

[0036]Add 0.1ml ethanol solution (1mM) of fluorescent probe RBAH and 0-3.0ml different volumes of 1mM mercury ion aqueous solution to different 10ml colorimetric tubes respectively, and dilute to 10ml with Tris-HCl buffer solution, and place for 1h. After constant volume, the concentration of the fluorescent probe is 10 mM, and the concentration of mercury ions is 0-300 mM. Transfer 3ml of the working solution to a 1cm fluorescence cuvette to record the fluorescence spectrum and read and record the fluorescence intensity at 576nm. 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 5-200mM, and the linear regression constant was 0.9825, indicating that the probe can quantitatively detect the concentration of mercury ions. The change ...

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Abstract

The invention relates to a reactive rhodamine fluorescent probe for detecting mercury ions, and a preparation method thereof. A structural formula of the reactive rhodamine fluorescent probe RBHA is shown in the description. The preparation method comprises the steps of adding rhodamine B and hydrazine hydrate into a solvent, reacting for 1-2 h under refluxing at a temperature of 80-90 DEG C; carrying out rotary evaporation; adding water and adjusting pH; filtering; and purifying to obtain rhodamine B hydrazide; dissolving the rhodamine B hydrazide and glyoxylic acid in a solvent; reacting overnight with stirring at a room temperature; filtering; and purifying to obtain the reactive rhodamine fluorescent probe. The reactive rhodamine fluorescent probe has high selectivity for the mercury ions, has no obvious interference with other common ions, can work in an environment with a wide pH scope ranging from 5 to 10, and has application prospects in bioluminescent imaging and analysis of environmental water samples.

Description

technical field [0001] The invention belongs to the field of fluorescent probe materials and preparation thereof, in particular to a reactive rhodamine fluorescent probe for detecting mercury ions and a preparation method thereof. Background technique [0002] Mercury is a typical toxic heavy metal that can cause permanent damage to the nervous system of organisms. Heavy metal pollution has become one of the major pollution sources in the current environmental pollution. Therefore, the development of simple, rapid and sensitive detection methods that can detect mercury ions in aqueous environment is of great significance to the monitoring of heavy metal pollution in water environment. The molecular fluorescent probe method has attracted much attention due to its characteristics of simplicity, rapidity, high sensitivity, good selectivity, easy automation and visual imaging. In recent years, there have been many reports on the detection of mercury ions based on small molecule...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D491/107G01N21/64
Inventor 张煊朱迎迎
Owner DONGHUA UNIV
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