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Mercury ion fluorescent probe based on rhodamine b and its preparation method and application

A fluorescent probe and mercury ion technology, applied in the field of mercury ion fluorescent probes, can solve the problems of complex preparation steps, poor water solubility and selectivity, and harsh test conditions of mercury ion fluorescent probes, and achieve relatively long absorption and emission wavelengths , high selectivity, and easy preparation

Active Publication Date: 2020-09-15
王可
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] One of the purposes of the present invention is to provide a mercury ion fluorescent probe based on rhodamine B, to solve the problems of existing mercury ion fluorescent probes such as poor water solubility and selectivity, low sensitivity, and harsh test conditions.
[0007] The second object of the present invention is to provide a method for preparing a mercury ion fluorescent probe based on rhodamine B, to solve the problem of complex preparation steps of the existing mercury ion fluorescent probe

Method used

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  • Mercury ion fluorescent probe based on rhodamine b and its preparation method and application
  • Mercury ion fluorescent probe based on rhodamine b and its preparation method and application
  • Mercury ion fluorescent probe based on rhodamine b and its preparation method and application

Examples

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Effect test

Embodiment 1

[0034] Weigh 239.5 mg of rhodamine B (0.5 mmol), dissolve it in 11 mL of 1,2-dichloroethane, add 0.4 mL of phosphorus oxychloride dropwise, and heat to reflux at 95 °C for 4 h. After the reaction was completed, 1,2-dichloroethane was distilled off under reduced pressure to obtain a red rhodamine B acid chloride intermediate.

[0035] Weigh 136.0 mg N,N - Dimethylselenourea (0.9 mmol), which was dissolved in 6 mL of tetrahydrofuran, and 1.6 mL of triethylamine was added dropwise with stirring. The rhodamine B acid chloride prepared in the previous steps was dissolved in 5 mL of tetrahydrofuran, added dropwise to the above solution, and reacted at 20 °C for 8 h. After the reaction was completed, the solvent was distilled off under reduced pressure to obtain a purple-red substance, and then 10 mL of twice distilled water was added to it, extracted three times with dichloromethane (20 mL*3), and the solvent was distilled off under reduced pressure to obtain a crude product . Th...

Embodiment 2

[0043] Weigh 239.5 mg of Rhodamine B (0.5 mmol), dissolve it in 10 mL of 1,2-dichloroethane, add 0.3 mL of phosphorus oxychloride dropwise, and heat to reflux at 90 °C for 5 h. After the reaction was completed, the solvent was distilled off under reduced pressure to obtain a red rhodamine B acid chloride intermediate.

[0044] Weigh 75.5 mg N,N - Dimethylselenourea (0.5 mmol), which was dissolved in 5 mL of acetonitrile, and 1.2 mL of triethylamine was added dropwise with stirring. The rhodamine B acid chloride prepared in the previous steps was dissolved in 5 mL of tetrahydrofuran, added dropwise to the above solution, and reacted at 35 °C for 5 h. After the reaction was completed, the solvent was distilled off under reduced pressure to obtain a purple-red substance, and 10 mL of twice distilled water was added to it, and extracted three times with dichloromethane (20 mL*3), and the solvent was distilled off under reduced pressure to obtain a crude product. The obtained cru...

Embodiment 3

[0046] Weigh 239.5 mg of Rhodamine B (0.5 mmol), dissolve it in 12 mL of 1,2-dichloroethane, add 0.5 mL of phosphorus oxychloride dropwise, and heat to reflux at 100 °C for 5 h. After the reaction was completed, the solvent was distilled off under reduced pressure to obtain a red rhodamine B acid chloride intermediate.

[0047] Weigh 151.1 mg N,N - Dimethylselenourea (1.0 mmol), which was dissolved in 6 mL of acetonitrile, and 2.0 mL of triethylamine was added dropwise with stirring. The rhodamine B acid chloride prepared in the previous steps was dissolved in 6 mL of acetonitrile, added dropwise to the above solution, and reacted at 10 °C for 10 h. After the reaction was completed, the solvent was distilled off under reduced pressure to obtain a purple-red substance, and then 10 mL of twice distilled water was added to it, extracted three times with dichloromethane (20 mL*3), and the solvent was distilled off under reduced pressure to obtain a crude product . The obtained ...

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Abstract

The invention provides a novel mercury ion fluorescent probe based on rhodamine B as well as a preparation method and application thereof. The structural formula of the novel mercury ion fluorescent probe based on rhodamine B is shown in the specification, and the preparation method comprises the following steps: preparing rhodamine B acyl chloride by adopting rhodamine B; carrying out a reactionbetween the obtained rhodamine B acyl chloride and N,N-dimethyl selenourea in a solvent containing triethylamine; removing the solvent through reduced pressure distillation, and carrying out extraction, rotary evaporation and column chromatography separation to obtain the novel mercury ion fluorescent probe based on rhodamine B. According to the invention, rhodamine B is used as a fluorescent group and N,N-dimethyl selenourea is used as a recognition group to synthesize a novel mercury ion fluorescent probe based on rhodamine B, which has strong selectivity to mercury ions and high sensitivity, and strong anti-interference capability to other metal ions, can be used as a basis for qualitative and quantitative detection of Hg<2+>, and is widely used for detection and in-situ online quantitative analysis of mercury ions.

Description

technical field [0001] The invention relates to a mercury ion fluorescent probe, in particular to a rhodamine B-based mercury ion fluorescent probe and its preparation method and application. Background technique [0002] There are many transition metal ions and heavy metal ions in nature, and some transition metal ions (such as Fe 3 + 、Cu 2+ , Zn 2+ etc.) play a very important role in living organisms, however, there are also some heavy metal ions (such as Hg 2+ 、Cd 2+ , Pb 2+ etc.) are extremely toxic at low concentrations and can be fatal to the organism. Mercury is a typical toxic transition metal ion, which is widely distributed in water, air and soil. The production of mercury mainly comes from natural and human activities, including volcanic eruptions, incineration and mining of domestic waste, especially the use of energy-saving fluorescent lamps, etc. [0003] According to the U.S. Environmental Protection Agency (EPA), the maximum concentration of mercury io...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1029C09K2211/1088G01N21/643
Inventor 王可尹海珍
Owner 王可
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