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Fluorescence probe for detecting iron ions, preparation and application

A technology of fluorescent probes and iron ions, which is applied in the field of heavy metal detection, can solve the problems of fewer fluorescent probes, achieve the effects of easy operation, easy-to-obtain products, and avoid the use of organic solvents

Inactive Publication Date: 2018-12-07
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently detects Fe in pure water media 3+ have very few fluorescent probes

Method used

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  • Fluorescence probe for detecting iron ions, preparation and application
  • Fluorescence probe for detecting iron ions, preparation and application
  • Fluorescence probe for detecting iron ions, preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] The synthesis of a kind of fluorescent probe (I) that detects iron ion of the present embodiment, concrete synthetic steps are as follows:

[0042] 1. Synthesis of intermediate RE

[0043] Rhodamine B (4.80g, 10mmol) was added to a 250mL three-neck flask, 100mL of ethanol was added, vigorously stirred at room temperature for 5min, and excess anhydrous ethylenediamine (5mL, 75mmol) was slowly added dropwise, and then the reaction temperature was raised to 80°C React for 4 hours. After the reaction is complete, spin the solvent to dry, add 100 mL of distilled water, extract with dichloromethane (100 mL×3), dry over anhydrous magnesium sulfate, remove the solvent by rotary evaporation, and dry under infrared light for 2 hours to obtain 3.80 g of a pink solid. The yield was 79.0%. The product identification data are as follows:

[0044] 1 H NMR (400MHz, CDCl 3 )δ: 7.92(dd, J=5.5,3.0Hz,1H),7.46(dd,J=5.5,3.1Hz,2H),7.11(dd,J=5.3,3.1Hz,1H),6.45(d,J =8.8Hz, 2H), 6.39(d, J=2...

Embodiment 2

[0058] The synthesis of a kind of fluorescent probe (I) that detects iron ion of the present embodiment, concrete synthetic steps are as follows:

[0059] 1. Synthesis of intermediate RE

[0060]Rhodamine B (4.80g, 10mmol) was added to a 250mL three-neck flask, 100mL of ethanol was added, vigorously stirred at room temperature for 5min, and excess anhydrous ethylenediamine (5mL, 75mmol) was slowly added dropwise, and then the reaction temperature was raised to 80°C React for 4 hours. After the reaction is complete, spin the solvent to dry, add 100 mL of distilled water, extract with dichloromethane (100 mL×3), dry over anhydrous magnesium sulfate, remove the solvent by rotary evaporation, and dry under infrared light for 2 hours to obtain 3.75 g of a pink solid. The yield was 77.9%.

[0061] 2. Synthesis of fluorescent probe RE1

[0062] Dissolve 3-methoxybenzaldehyde (0.21g, 1.5mmol) in 20mL of methanol, add dropwise to 30mL of methanol containing RE (0.48g, 1mmol), after t...

Embodiment 3

[0070] The synthesis of a kind of fluorescent probe (I) that detects iron ion of the present embodiment, concrete synthetic steps are as follows:

[0071] 1. Synthesis of intermediate RE

[0072] Rhodamine B (4.80g, 10mmol) was added to a 250mL three-neck flask, 100mL of ethanol was added, vigorously stirred at room temperature for 5min, and excess anhydrous ethylenediamine (5mL, 75mmol) was slowly added dropwise, and then the reaction temperature was raised to 80°C React for 4 hours. After the reaction is complete, spin the solvent to dry, add 100 mL of distilled water, extract with dichloromethane (100 mL×3), dry over anhydrous magnesium sulfate, remove the solvent by rotary evaporation, and dry under infrared light for 2 hours to obtain 3.77 g of a pink solid. The yield was 78.4%.

[0073] 2. Synthesis of small organic molecule probe RE1

[0074] Dissolve 3-methoxybenzaldehyde (0.21g, 1.5mmol) in 20mL of methanol, add dropwise to 30mL of methanol containing RE (0.48g, 1mm...

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Abstract

The invention belongs to the technical field of heavy metal detection and discloses a fluorescence probe for detecting iron ions, preparation and application thereof. The chemical structure of the fluorescence probe is as shown in formula (I). A preparation method comprises the following steps: dropwise adding anhydrous ethylenediamine into an ethanol solution of rhodamine B, reacting under the condition of heating and refluxing, separating and purifying the product, thereby acquiring an intermediate; dissolving 3-methoxybenzaldehyde, 5-bromine-2 furfural, 3-hydroxybenzaldehyde or 3,4-dimethoxy benzaldehyde in methyl alcohol, and then dropwise adding into a methanol solution of the intermediate, reacting under the condition of heating and refluxing, and then cooling to room temperature; adding sodium borohydride in ice bath, stirring and uniformly mixing, continuing to react under the condition of heating and refluxing, separating and purifying the product, thereby acquiring the fluorescence probe. The preparation method disclosed by the invention is simple. The acquired product can realize ultraviolet and fluorescence dual-response detection of Fe<3+>, can detect Fe<3+> in pure aqueous solution and has a wide application prospect in the fields of chemical engineering, environment, biological medicines, and the like.

Description

technical field [0001] The invention belongs to the technical field of heavy metal detection, and in particular relates to a fluorescent probe for detecting iron ions and its preparation and application. Background technique [0002] Iron is a transition metal element and also a heavy metal element. It exists widely in nature and has a wide range of industrial uses, such as steelmaking and various equipment. It is also an indispensable substance in living organisms. In living organisms, Fe 3+ It plays a key role in many physiological processes, such as oxygen transport, electron transfer process and DNA and RNA synthesis pathways, etc. Abnormal Fe in organisms 3+ Concentrations can cause various physiological disorders such as heart disease, hepatitis, cancer and other organ dysfunctions. Furthermore, excess Fe in the environment 3+ It will cause water and soil pollution, which will affect industries such as plastics, textiles, paper, brewing and food. Therefore to achie...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D491/107G01N21/64
CPCC07D491/107C09K11/06C09K2211/1007C09K2211/1029C09K2211/1088G01N21/643
Inventor 颜金武张雷吴紫盈李晶
Owner SOUTH CHINA UNIV OF TECH
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