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Rhodamine B derivatives-based multi-channel fluorescent probe as well as preparation method and application thereof

A fluorescent probe and multi-channel technology, applied in the field of fluorescent probes, can solve problems such as central nervous system, hematopoietic system, immune system adverse effects, damage to cell structure and composition, gastrointestinal mucosal injury, etc., to achieve multifunctionality , strong operability, and the effect of saving testing costs

Active Publication Date: 2018-02-02
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Cr 3+ The lack of will cause many diseases such as diabetes and arteriosclerosis, but when Cr 3+ When the content is too high, it will destroy the cell structure and composition, and cause harm to the human body
Al 3+ It is not an essential trace element for the human body, but if you usually take too much Al 3+ It can cause senile dementia and have adverse effects on the central nervous system, hematopoietic system, immune system, liver and kidney of the human body
Trace amount of Hg 2+ It can be used as a disinfectant, but if a high dose of Hg is accidentally ingested 2+ , will not only cause gastrointestinal mucosal injury and massive bleeding, but also damage the kidneys, leading to acute renal failure and even death

Method used

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  • Rhodamine B derivatives-based multi-channel fluorescent probe as well as preparation method and application thereof
  • Rhodamine B derivatives-based multi-channel fluorescent probe as well as preparation method and application thereof
  • Rhodamine B derivatives-based multi-channel fluorescent probe as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The reaction formula for synthesizing a multi-channel fluorescent probe based on rhodamine B derivatives is as follows:

[0028]

[0029] Its preparation method comprises the following concrete steps:

[0030] (1) Synthesis of Compound A: Weigh (1.2g, 2.5mmol) rhodamine B, dissolve it in 30mL absolute ethanol, stir vigorously at room temperature, add 5.0mL 85% to 90% hydrazine hydrate dropwise, and dropwise add Then continue to stir for 0.5h, then raise the temperature and reflux for 12h until the solution turns orange-yellow, cool down, remove the solvent by rotary evaporation under reduced pressure, add 1mol / L HCl 50mL, add 1mol / L NaOH 70mL under stirring conditions until the pH of the solution is about 9 , a large amount of precipitation appeared, suction filtered, washed 3 times with distilled water, placed in a vacuum oven and dried overnight to obtain Compound A with a yield of 78%; wherein, the molar ratio of Rhodamine B to hydrazine hydrate was 0.25:1 .

[...

Embodiment 2

[0045] The reaction formula for synthesizing a multi-channel fluorescent probe based on rhodamine B derivatives is as follows:

[0046]

[0047] The preparation method comprises the following steps:

[0048] (1) Synthesis of Compound A: Weigh (1.2g, 2.5mmol) Rhodamine B, dissolve it in 40mL of absolute ethanol, stir vigorously at room temperature, add 2.5mL of 85% to 90% hydrazine hydrate dropwise, after the addition is complete Continue to stir for 0.5h, then raise the temperature and reflux for 12h until the solution turns orange-yellow, cool, remove the solvent by rotary evaporation under reduced pressure, add 1mol / L HCl 50mL, add 1mol / L NaOH 70mL under stirring conditions until the pH of the solution is about 9, A large amount of precipitate appeared, filtered with suction, washed with distilled water for 3 times, and dried overnight in a vacuum oven to obtain Compound A with a yield of 78%; wherein, the molar ratio of rhodamine B to hydrazine hydrate was 0.5:1.

[004...

Embodiment 3

[0061] The reaction formula for synthesizing a multi-channel fluorescent probe based on rhodamine B derivatives is as follows:

[0062]

[0063] The preparation method comprises the following steps:

[0064] (1) Synthesis of Compound A: Weigh (1.2g, 2.5mmol) Rhodamine B, dissolve it in 50mL absolute ethanol, stir vigorously at room temperature, add 0.5mL 85% to 90% hydrazine hydrate dropwise, and dropwise complete Then continue to stir for 0.5h, then raise the temperature and reflux for 12h until the solution turns orange-yellow, cool down, remove the solvent by rotary evaporation under reduced pressure, add 1mol / L HCl 50mL, add 1mol / L NaOH 70mL under stirring conditions until the pH of the solution is about 9 , a large amount of precipitation appeared, suction filtered, washed 3 times with distilled water, placed in a vacuum oven and dried overnight to obtain Compound A with a yield of 82%; wherein, the molar ratio of Rhodamine B to hydrazine hydrate was 1:1 .

[0065] (...

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Abstract

The invention discloses a rhodamine B derivatives-based multi-channel fluorescent probe, a preparation method and application thereof. The chemical formula of the fluorescent probe is C34H34N8O2; thepreparation method includes steps of preparing a compound A by mixing rhodamine B and hydrazine hydrate in accordance with a molar ratio of (0.25-1):1; then preparing a compound B by mixing the compound A and glyoxal in accordance with the molar ratio of (0.25-1):1; dissolving the compound B and diaminomaleonitrile in anhydrous ethanol in accordance with the molar ratio of (0.25-1):1; adding 2-3 drops of glacial acetic acid and preparing the multi-channel fluorescent probe through stirring, refluxing, distillation and separation. The fluorescent probe is applied to detection of trivalent metalion and Hg<2+> ion. Furthermore, the invention has the significant advantage that the fluorescent probe can enhance recognition of Fe<3+>, Cr<3+>, Al<3+> and Hg<2+> fluorescence in identical solventenvironment, with high detection sensitivity.

Description

technical field [0001] The invention belongs to the field of fluorescent probes, in particular to a multi-channel fluorescent probe based on rhodamine B derivatives, a preparation method and an application. Background technique [0002] Fluorescent molecular probes are widely used in the detection of various metal ions due to their advantages of good selectivity, high sensitivity, simplicity and speed, and the need for expensive instruments. Among many metal ion detection methods, the fluorescent molecular probe recognition method has attracted much attention due to its good selectivity, high sensitivity, and the ability to realize switch operation. Rhodamine-based dyes have the advantages of high fluorescence quantum yield, large rigid planar structure, good water solubility, low toxicity, and the maximum emission wavelength is in the red-visible region, but can realize naked-eye recognition and rapid response. Derivative fluorescent probe molecules are rarely reported in ...

Claims

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Application Information

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IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1029C09K2211/1088G01N21/64G01N21/6428G01N21/643G01N2021/6417G01N2021/6443
Inventor 赵红薛兴颖江道勇张晗贺祖茂杨买娥
Owner SOUTHEAST UNIV
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