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Water-soluble rhodamine-based fluorescent/colorimetric dual-mode probe as well as preparation method and application thereof

A dual-mode probe, water-soluble technology, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of no accurate pH application range, inability to use biological samples for detection, cumbersome sample preparation process, etc., to achieve High practical application value, good water solubility and biocompatibility, and the effect of simplifying the preparation process

Active Publication Date: 2021-01-01
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The fluorescent probe synthesized by the invention can detect Fe 3+ Naked eye detection does not require any equipment, but the probe also has the problem of poor water solubility, and must be dissolved with organic reagents when used, the sample preparation process is cumbersome, and the detection in aqueous samples is greatly limited; in addition, The biological toxicity of the rhodamine 6G probe is unknown, it cannot be used for the detection of biological samples, and there is no accurate pH range

Method used

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  • Water-soluble rhodamine-based fluorescent/colorimetric dual-mode probe as well as preparation method and application thereof
  • Water-soluble rhodamine-based fluorescent/colorimetric dual-mode probe as well as preparation method and application thereof
  • Water-soluble rhodamine-based fluorescent/colorimetric dual-mode probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049]A preparation method of a water-soluble rhodamine-based fluorescence / colorimetric dual-mode probe, comprising the steps:

[0050]Dissolve 0.958g rhodamine 6G in 30mL ethanol, add 3.0g hydrazine hydrate aqueous solution (mass concentration of 85%) dropwise at room temperature, after 10 minutes the addition is complete, then increase the system temperature at 78℃, stir and reflux for 12h, stop Heat and cool to room temperature, filter to obtain the solid intermediate product, wash the solid intermediate product with ethanol / ether (volume ratio 1:1), and dry in a vacuum dryer to obtain rhodamine 6G hydrazide;

[0051]Dissolve 8g polyethylene glycol 4000 and 0.9g 4-aldehyde benzoic acid in 50mL tetrahydrofuran, under nitrogen atmosphere, 0.09g dicyclohexyl diimide and 1.64g 4-dimethylaminopyridine catalyst, room temperature After reacting for 24 hours, the obtained reaction solution was filtered to remove the precipitate, and the obtained filtrate was rotary evaporated to obtain a solid...

Embodiment 2

[0056]A preparation method of a water-soluble rhodamine-based fluorescence / colorimetric dual-mode probe, comprising the steps:

[0057]Dissolve 0.958g rhodamine 6G in 30mL ethanol, drop by drop 3.0g hydrazine hydrate aqueous solution (mass concentration 85%) at room temperature, add dropwise after 10min, then raise the system temperature to 78℃, stir and reflux for 12h, stop Heat and cool to room temperature, filter to obtain the solid intermediate product, wash the solid intermediate product with ethanol / ether (volume ratio 1:1), and dry in a vacuum dryer to obtain rhodamine 6G hydrazide;

[0058]Dissolve 4g polyethylene glycol 2000 and 0.9g 4-aldehyde benzoic acid in 50mL tetrahydrofuran, under nitrogen atmosphere, 0.09g dicyclohexyl diimide and 1.64g 4-dimethylaminopyridine catalyst, room temperature After reacting for 24 hours, the obtained reaction solution was filtered to remove the precipitate, and the obtained filtrate was rotary evaporated to obtain a solid intermediate product, ...

Embodiment 3

[0061]A preparation method of a water-soluble rhodamine-based fluorescence / colorimetric dual-mode probe, comprising the steps:

[0062]Dissolve 0.958g rhodamine 6G in 30mL ethanol, add 10.0g hydrazine hydrate aqueous solution (mass concentration of 50%) dropwise at room temperature, add dropwise after 10 minutes, then raise the system temperature to 78℃, stir and reflux for 12h, stop Heat and cool to room temperature, filter to obtain the solid intermediate product, wash the solid intermediate product with ethanol / ether (volume ratio 1:1), and dry in a vacuum dryer to obtain rhodamine 6G hydrazide;

[0063]Dissolve 4g polyethylene glycol 2000 and 0.9g 4-aldehyde benzoic acid in 50mL tetrahydrofuran, under nitrogen atmosphere, 0.09g dicyclohexyl diimide and 1.64g 4-dimethylaminopyridine catalyst, room temperature After reacting for 24 hours, the obtained reaction solution was filtered to remove the precipitate, and the obtained filtrate was rotary evaporated to obtain a solid intermediate ...

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Abstract

The invention provides a water-soluble rhodamine-based fluorescence / colorimetric dual-mode probe, and a preparation method and application thereof. The preparation method of the probe comprises the following steps: reacting rhodamine 6G with hydrazine hydrate to prepare rhodamine 6G hydrazide; reacting polyethylene glycol with 4-aldehyde benzoic acid to prepare benzaldehyde terminated polyethyleneglycol; and reacting the rhodamine 6G hydrazide with the benzaldehyde terminated polyethylene glycol to prepare the water-soluble rhodamine-based fluorescent / colorimetric dual-mode probe. The obtained dual-mode probe has good water solubility, biocompatibility and safety, and can be used in the field of bioluminescence imaging or disease diagnosis; and the probe is used for detecting ferric ions,is simple in sample preparation, can be observed through fluorescence emission and naked eyes, shows high selectivity, sensitivity and anti-interference capability, and is wide in pH application range.

Description

Technical field[0001]The invention relates to a water-soluble rhodamine-based fluorescence / colorimetric dual-mode probe and a preparation method and application thereof, belonging to the technical field of organic synthesis and spectral detection.Background technique[0002]Iron is the transition metal element with the highest content in humans or animals, and it plays a vital role in the metabolism of organisms. Iron deficiency in organisms can lead to a decrease in ferritin, causing anemia, cancer or other diseases; excessive iron can interfere with the absorption of other nutrients by organisms, causing biological organ damage, such as Alzheimer’s disease and liver cirrhosis , Even death. Therefore, how to accurately determine the iron content in domestic water or organisms is of great significance in the fields of medicine and health.[0003]At present, the commonly used iron ion analysis and detection methods mainly include atomic absorption spectroscopy, inductively coupled plasma...

Claims

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Application Information

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IPC IPC(8): C08G65/333C08G65/332C07D519/00C09K11/06G01N21/31G01N21/33G01N21/64G01N21/78
CPCC07D519/00C08G65/3326C08G65/33396C09K11/06C09K2211/1033C09K2211/1475G01N21/31G01N21/33G01N21/64G01N21/6428G01N21/643G01N21/6456G01N21/78G01N2021/6417G01N2021/6439G01N2021/6495G01N2021/6497
Inventor 邱晓勇郝京诚崔基炜黄俊王彦滔甄曰菊
Owner SHANDONG UNIV
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