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A water-soluble rhodamine-based fluorescence/colorimetric dual-mode probe and its preparation method and application

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: 2021-08-06
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • A water-soluble rhodamine-based fluorescence/colorimetric dual-mode probe and its preparation method and application
  • A water-soluble rhodamine-based fluorescence/colorimetric dual-mode probe and its preparation method and application
  • A water-soluble rhodamine-based fluorescence/colorimetric dual-mode probe and its preparation method and application

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Embodiment 1

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

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

[0051] Dissolve 8g of polyethylene glycol 4000 and 0.9g of 4-formylbenzoic acid in 50mL of tetrahydrofuran, under nitrogen atmosphere, under the action of 0.09g of dicyclohexyldiimine and 1.64g of 4-dimethylaminopyridine catalyst, at room temperature After reacting for 24 hours, the obtained reaction solution was filtered to remove the precipitate, a...

Embodiment 2

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

[0057] Dissolve 0.958g rhodamine 6G in 30mL ethanol, add 3.0g hydrazine hydrate aqueous solution (mass concentration: 85%) dropwise at room temperature, and complete the dropwise addition in 10 minutes, then increase the system temperature at 78°C, stir and reflux for 12h, stop Heat and cool to room temperature, filter to obtain a solid intermediate product, wash the solid intermediate product with ethanol / diethyl ether (volume ratio 1:1), and dry it in a vacuum desiccator to obtain rhodamine 6G hydrazide;

[0058] Dissolve 4g polyethylene glycol 2000 and 0.9g 4-formylbenzoic acid in 50mL tetrahydrofuran, under nitrogen atmosphere, under the action of 0.09g dicyclohexyldiimine 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 fi...

Embodiment 3

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

[0062] Dissolve 0.958g of rhodamine 6G in 30mL of ethanol, drop in 10.0g of an aqueous solution of hydrazine hydrate (mass concentration: 50%) at room temperature, and finish adding dropwise in 10 minutes, then increase the temperature of the system at 78°C, stir and reflux for 12 hours, stop Heat and cool to room temperature, filter to obtain a solid intermediate product, wash the solid intermediate product with ethanol / diethyl ether (volume ratio 1:1), and dry it in a vacuum desiccator to obtain rhodamine 6G hydrazide;

[0063] Dissolve 4g polyethylene glycol 2000 and 0.9g 4-formylbenzoic acid in 50mL tetrahydrofuran, under nitrogen atmosphere, under the action of 0.09g dicyclohexyldiimine and 1.64g 4-dimethylaminopyridine catalyst, room temperature After reacting for 24 hours, the obtained reaction solution was filtered to remove the precipitate, and ...

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Abstract

The invention provides a water-soluble rhodamine-based fluorescence / colorimetric dual-mode probe, a preparation method and application thereof. The preparation method of the probe of the present invention comprises the following steps: Rhodamine 6G and hydrazine hydrate are reacted to prepare rhodamine 6G hydrazide; polyethylene glycol and 4-formylbenzoic acid are reacted to prepare benzaldehyde-terminated polyethylene Diol; rhodamine 6G hydrazide and benzaldehyde-terminated polyethylene glycol were reacted to prepare a water-soluble rhodamine-based fluorescent / colorimetric dual-mode probe. The dual-mode probe obtained in the present invention has good water solubility, biocompatibility and safety, and can be used in the field of bioluminescent imaging or disease diagnosis; it can be used to detect ferric ions, the sample preparation is simple, and it can be observed by fluorescence emission and naked eyes , and shows high selectivity, sensitivity and anti-interference ability, and the pH is applicable to a wide 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 fields of organic synthesis and spectral detection. Background technique [0002] Iron is the transition metal element with the highest content in the human body or animal body, and plays a vital role in the metabolism of organisms. Iron deficiency in organisms will lead to a decrease in iron-containing proteins, causing anemia, cancer or other diseases; excessive iron will interfere with the absorption of other nutrients by organisms, causing damage to biological organs, such as Alzheimer's disease and liver cirrhosis , even death. Therefore, how to accurately measure the content of iron 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 atom...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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