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Copper ion ratio type fluorescent probe based on rhodamine derivative and preparation method and application

A fluorescent probe, copper ion technology, used in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of lack of structural diversity, application limitations, etc., achieve low detection limit, strong anti-interference ability, preparation simple method effect

Active Publication Date: 2019-08-23
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although many rhodamine derivative probes for detecting copper ions have been reported, there is still a lack of structural diversity and application limitations.

Method used

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  • Copper ion ratio type fluorescent probe based on rhodamine derivative and preparation method and application
  • Copper ion ratio type fluorescent probe based on rhodamine derivative and preparation method and application
  • Copper ion ratio type fluorescent probe based on rhodamine derivative and preparation method and application

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Embodiment 1

[0021] The present invention prepares the reaction formula of the copper ion ratio type fluorescent probe based on rhodamine derivatives as follows:

[0022]

[0023] The method for preparing the copper ion ratio fluorescent probe based on rhodamine derivatives in the present invention comprises the following steps:

[0024] (1) Synthesis of Rhodamine B hydrazide intermediate (Rh-HH): Dissolve 2.40g (5mmol) Rhodamine B in 50ml of absolute ethanol, add 7ml of hydrazine hydrate dropwise under stirring, after dropping, reflux for 5-20h , TLC monitors the reaction process until the solution turns from purplish red to clear light yellow; after the reaction, the solvent is distilled off under reduced pressure to obtain a yellow sticky solid; add 1mol / L hydrochloric acid solution until the solid is completely dissolved, and then add L of NaOH solution to adjust the pH to 9-10, filter, wash the filter cake with distilled water, and dry in a vacuum oven to obtain a powdery solid wit...

Embodiment 2

[0037] The method for preparing the copper ion ratio fluorescent probe based on rhodamine derivatives in the present invention comprises the following steps:

[0038] (1) Synthesis of Rhodamine B hydrazide intermediate (Rh-HH): Dissolve 12.0g (25mmol) Rhodamine B in 125ml of absolute ethanol, add 25ml of hydrazine hydrate dropwise under stirring, after dropping, reflux for 5-20h , TLC monitors the reaction process until the solution turns from purplish red to clear light yellow; after the reaction, the solvent is distilled off under reduced pressure to obtain a yellow sticky solid; add 1mol / L hydrochloric acid solution until the solid is completely dissolved, and then add L of NaOH solution to adjust the pH to 9-10, filter, wash the filter cake with distilled water, and dry in a vacuum oven to obtain a powdery solid with a yield of 60-85%;

[0039] (2) Synthesis of fluorescent probe (RhF): Weigh the intermediate Rh-HH (0.2281g, 0.5mmol) and dissolve it in 50mL of absolute etha...

Embodiment 3

[0041] The method for preparing the copper ion ratio fluorescent probe based on rhodamine derivatives in the present invention comprises the following steps:

[0042] (1) Synthesis of Rhodamine B hydrazide intermediate (Rh-HH): Dissolve 2.40g (5mmol) Rhodamine B in 25ml of absolute ethanol, add 7ml of hydrazine hydrate dropwise under stirring, after dropping, reflux for 5-20h , TLC monitors the reaction process until the solution turns from purplish red to clear light yellow; after the reaction, the solvent is distilled off under reduced pressure to obtain a yellow sticky solid; add 1mol / L hydrochloric acid solution until the solid is completely dissolved, and then add L of NaOH solution to adjust the pH to 9-10, filter, wash the filter cake with distilled water, and dry in a vacuum oven to obtain a powdery solid with a yield of 65-85%;

[0043] (2) Synthesis of fluorescent probe (RhF): Weigh the intermediate Rh-HH (0.4562g, 1mmol) and dissolve it in 10mL of absolute ethanol; ...

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Abstract

The invention discloses a copper ion ratio type fluorescent probe based on a rhodamine derivative and a preparation method and application. The chemical formula of the fluorescent probe is C41H45N5O2.A rhodamine B hydrazide intermediate is firstly prepared, then an ethanol solution of the rhodamine B hydrazide intermediate and an ethanol solution of 1,3,3-trimethyl-2-(formylmethylene)indoline arerespectively prepared, the ethanol solution of 1,3,3-trimethyl-2-(formylmethylene)indoline is dropwise added into the ethanol solution of the rhodamine B hydrazide intermediate for carrying out a reaction, and the distillation and purification is performed to obtain the fluorescent probe. The fluorescent probe is applied to detect Cu<2+>. The fluorescent probe can specifically recognize Cu<2+>, the anti-interference ability is strong, the detection limit is low, the sensitivity is high, the fluorescent probe can be well applied to the Cu<2+> detection in the environment or organisms, and thefluorescent probe has important application values; and the preparation method of the fluorescent probe is simple, and the operability is strong.

Description

technical field [0001] The invention belongs to the field of fluorescent probe preparation, in particular to a copper ion ratio fluorescent probe based on rhodamine derivatives, a preparation method and application. Background technique [0002] As the third indispensable trace element for human health, copper plays a vital role in maintaining basic physiological processes. The US Environmental Protection Agency (EPA) stipulates that the maximum content of copper ions in drinking water is 1.3ppm (-20μM). Fluorescent probes combined with bioimaging technology can be used to detect metal ions in organisms, which can realize real-time and in situ detection of substances, and even monitor physiological reaction processes. Therefore, fluorescent probes have broad application prospects. [0003] Fluorescent probes based on the mechanism of fluorescence resonance energy transfer (FRET) contain two fluorescent groups, one group is an energy donor, and the other group is an energy ac...

Claims

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Application Information

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IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1029C09K2211/1088G01N21/643G01N21/6447
Inventor 赵红张娇
Owner SOUTHEAST UNIV
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