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A kind of rhodamine derivative bifunctional fluorescent probe and its application

A fluorescent probe and dual-function technology, which is applied in rhodamine derivative-based dual-functional fluorescent probes and its application fields, to achieve good sensing properties, low detection limit, and cost-saving detection effects

Active Publication Date: 2019-03-12
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, bifunctional fluorescent molecules based on rhodamine derivatives that can realize naked-eye recognition, reversible operation, and recyclability are rarely reported in the literature.

Method used

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  • A kind of rhodamine derivative bifunctional fluorescent probe and its application
  • A kind of rhodamine derivative bifunctional fluorescent probe and its application
  • A kind of rhodamine derivative bifunctional fluorescent probe and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Synthesis of bifunctional fluorescent probes based on rhodamine derivatives

[0026] The reaction formula for synthesizing rhodamine derivative-based bifunctional fluorescent probes:

[0027]

[0028] Concrete steps for synthesizing rhodamine derivative-based bifunctional fluorescent probes:

[0029] 1) Synthesis of Rhodamine B hydrazide intermediate M1: Weigh 1.2g of Rhodamine B, dissolve it in 30mL of absolute ethanol, stir vigorously at room temperature, add 3.0-5.0mL of 85wt% hydrazine hydrate dropwise, and the addition is complete Then 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 1N HCl 50-60mL, add 1mol / L NaOH 70-80mL under stirring conditions until the solution pH is Around 9-10, a large amount of precipitation appeared, filtered with suction, washed with distilled water for 3 times, and dried overnight in a...

Embodiment 2

[0035] Example 2: Rhodamine Derivatives Bifunctional Fluorescent Probes to VO 2+ and Cu 2+ Selective detection of:

[0036] 20 μmol / L rhodamine derivative bifunctional fluorescent probe dimethyl sulfoxide (DMSO) and 0.01mol / L, Tris-HCl buffer solution of pH=7.4 with a volume ratio of 4:1 mixed solution, add respectively 200μmol / L of metal ions (Mg 2+ , Al 3+ , Ca 2+ , Cr 3+ , Mn 2+ , Fe 2+ , Fe 3+ ,Co 2+ , Ni 2+ , Zn 2+ , Ag + , Cd 2+ , Sn 2+ , Ba 2+ , Hg 2+ , Pb 2+ , VO 2+, La 3+ , Ce 3+ , Pr 3+ ,Nd 3+ , Sm 3+ , Eu 3+ , Dy 3+ , Er 3+ , Th 4+ , Cu 2+ ), after 0.5h, detect the changes in the fluorescence emission spectrum and the ultraviolet-visible absorption spectrum of the solution. It can be seen from the detection results that the rhodamine derivative bifunctional fluorescent probe itself has almost no emission peak at 586nm, and almost no absorption peak at 560nm; when adding VO 2+ After ionization, the rhodamine derivative bifunctional fluore...

Embodiment 3

[0037] Example 3: Rhodamine Derivatives Bifunctional Fluorescent Probes to VO 2+ and Cu 2+ Fluorescence titration experiment:

[0038] 20 μmol / L rhodamine derivatives bifunctional fluorescent probe dimethyl sulfoxide (DMSO) and 0.05mol / L, pH=8 Tris-HCl buffer volume ratio is a mixed solution of 7:3, gradually increasing Joined VO 2+ and Cu 2+ After 0.5h, test the fluorescence spectrum and absorption spectrum of each sample. It can be seen from the test results that with VO 2+ and Cu 2+ As the concentration increases gradually, the fluorescence intensity of the rhodamine derivative bifunctional fluorescent probe solution at 586nm increases gradually, and the absorption intensity at 560nm also increases gradually. When VO 2+ and Cu 2+ When the concentrations of the rhodamine derivatives were increased to about 400 μmol / L, the titration reached saturation, and the emission intensity and absorption intensity no longer increased; 2+ and Cu 2+ have good sensing properties. ...

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Abstract

The invention discloses a rhodamine derivative double-function fluorescent probe and application thereof. The structural formula of the probe is disclosed in the specification. The fluorescent probe can respectively detect and identify VO<2+> and Cu<2+> in a VO<2+> / Cu<2+> buffer solution by using fluorescent and ultraviolet visible absorption spectra. The probe has the advantages of excellent identification selectivity for VO<2+> and Cu<2+>, high antijamming ability, favorable sensing property, low detection limit and high detection sensitivity. After the pyrophosphate ions are added subsequently, the pyrophosphate ions are combined with the VO<2+> and Cu<2+>, and the coordinative metal ions are released; and the hydrazide in the fluorescent probe becomes the closed ring state again, and the fluorescence of the system quickly is lowered, thereby implementing the reversible operation of the fluorescent probe molecule. The fluorescent probe can be well applied to the detection of Cu<2+> and VO<2+> in environmental pollutants or organisms.

Description

technical field [0001] The invention relates to a rhodamine derivative bifunctional fluorescent probe and its application, belonging to the technical field of metal cation recognition. Background technique [0002] Fluorescent molecular probes are widely used in industry, agriculture, medicine, environmental detection, etc. It has a wide range of applications and has attracted extensive attention from researchers in the field of chemistry. In recent years, designing and synthesizing highly selective fluorescent probes to detect transition and heavy metal ions is one of the important research directions in the field of chemical research. [0003] Copper is an important trace element and essential nutrient in living systems. Among various transition and heavy metal ions, copper ranks third in the human body except zinc and iron. It plays a key role in biological systems as a catalyst for a variety of metalloenzyme cofactors. Cu 2+ Plays an important role in the environmen...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64G01N21/31
CPCC07D491/107C09K11/06C09K2211/1029C09K2211/1088G01N21/31G01N21/64G01N21/6428G01N21/643G01N2021/6417G01N2021/6443
Inventor 赵红江道勇王志飞王肖肖薛兴颖汤雪娇
Owner SOUTHEAST UNIV