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Novel mercury ion fluorescent probe based on rhodamine B as well as preparation method and application thereof

A fluorescent probe and mercury ion technology, applied in the field of mercury ion fluorescent probes, can solve the problems of complex preparation steps of mercury ion fluorescent probes, poor water solubility and selectivity, harsh test conditions, etc., and achieves strong anti-interference ability and easy Storage, easy preparation effect

Active Publication Date: 2018-06-29
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 novel 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 novel 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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  • Novel mercury ion fluorescent probe based on rhodamine B as well as preparation method and application thereof
  • Novel mercury ion fluorescent probe based on rhodamine B as well as preparation method and application thereof
  • Novel mercury ion fluorescent probe based on rhodamine B as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0034] Weigh 239.5mg of rhodamine B (0.5mmol), dissolve it in 11mL of 1,2-dichloroethane, add 0.4mL of phosphorus oxychloride dropwise, and heat to reflux at 95°C for 4h. 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 of N,N-dimethylselenourea (0.9 mmol), dissolve it in 6 mL of tetrahydrofuran, and add 1.6 mL of triethylamine dropwise with stirring. Dissolve the rhodamine B acid chloride prepared in the previous steps in 5 mL of tetrahydrofuran, add dropwise to the above solution, and react 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 10 mL of twice-distilled water was added thereto, extracted three times with dichloromethane (20 mL*3), and the solvent was distilled off under reduced pressure to obtain a crude product. The resulting crude product is sepa...

Embodiment 2

[0043]Weigh 239.5mg of rhodamine B (0.5mmol), dissolve it in 10mL of 1,2-dichloroethane, add 0.3mL of phosphorus oxychloride dropwise, and heat at reflux at 90°C for 5h. 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 of N,N-dimethylselenourea (0.5 mmol), dissolve it in 5 mL of acetonitrile, and add 1.2 mL of triethylamine dropwise with stirring. Dissolve the rhodamine B acid chloride prepared in the preceding steps in 5 mL of tetrahydrofuran, add dropwise to the above solution, and react 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 thereto, extracted three times with dichloromethane (20 mL*3), and the solvent was distilled off under reduced pressure to obtain a crude product. The resulting crude product is separated by co...

Embodiment 3

[0046] Weigh 239.5mg of rhodamine B (0.5mmol), dissolve it in 12mL of 1,2-dichloroethane, add 0.5mL of phosphorus oxychloride dropwise, and heat at reflux at 100°C for 5h. 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 of N,N-dimethylselenourea (1.0 mmol), dissolve it in 6 mL of acetonitrile, and add 2.0 mL of triethylamine 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 10 mL of twice-distilled water was added thereto, extracted three times with dichloromethane (20 mL*3), and the solvent was distilled off under reduced pressure to obtain a crude product. The resulting crude product is separa...

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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 novel mercury ion fluorescent probe based on rhodamine B and its preparation method and application. Background technique [0002] There are many transition metal ions and heavy metal ions in nature, some of which transition metal ions (such as Fe 3 + 、Cu 2+ , Zn 2+ etc.) play a very important role in 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 organisms. 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 mercur...

Claims

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Application Information

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Patent Type & Authority Applications(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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