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Fluorescence probe for detecting three-valent iron ions and preparation method of fluorescence probe

A technology for fluorescent probes and intermediates, which is applied in the field of fluorescent probes for detecting ferric ions and its preparation, can solve the problems of complex methods, inapplicability of fast and on-line monitoring, and time-consuming, and achieve easy-to-obtain and easy-to-use products. Simple operation and post-processing

Inactive Publication Date: 2019-01-18
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Traditional methods such as atomic absorption spectroscopy, inductively coupled plasma mass spectrometry, and electrochemistry can be used for Fe 3+ detection, but these methods are relatively complex, time-consuming and not suitable for rapid and on-line monitoring of Fe 3+

Method used

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  • Fluorescence probe for detecting three-valent iron ions and preparation method of fluorescence probe
  • Fluorescence probe for detecting three-valent iron ions and preparation method of fluorescence probe
  • Fluorescence probe for detecting three-valent iron ions and preparation method of fluorescence probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The synthesis of a kind of organic small molecule probe (I) of the present embodiment, concrete synthetic steps are as follows:

[0041] (1) Synthesis of Intermediate 1

[0042] Rhodamine B (4.80g, 10mmol) was added to a 250mL three-necked flask, 100mL of ethanol was added, vigorously stirred at room temperature for 5 minutes, and excess hydrazine hydrate monohydrate (12mL, 197mmol) was slowly added dropwise, then the reaction was heated to 80 React at ℃ for 4 hours. After the reaction is complete, spin dry the solvent, add 1mol / L hydrochloric acid solution until the solution turns clear red, slowly add 1mol / L sodium hydroxide solution until the pH is between 9 and 10, and use a cloth The obtained solid was washed three times with 50 mL of distilled water, and dried with an infrared lamp to obtain 3.40 g of a pink solid with a yield of 75.0%.

[0043] 1 H NMR (400MHz, CDCl 3 )δ7.96(d, J=5.1Hz, 1H), 7.47(d, J=3.6Hz, 2H), 7.12(d, J=6.2Hz, 1H), 6.62-6.38(m, 4H), 6.31( ...

Embodiment 2

[0058] The synthesis of a kind of organic small molecule probe (I) of the present embodiment, concrete synthetic steps are as follows:

[0059] (1) Synthesis of Intermediate 1

[0060] Rhodamine B (4.80g, 10mmol) was added to a 250mL three-necked flask, 100mL of ethanol was added, vigorously stirred at room temperature for 5 minutes, and excess hydrazine hydrate monohydrate (12mL, 197mmol) was slowly added dropwise, then the reaction was heated to 80 React at ℃ for 4 hours. After the reaction is complete, spin dry the solvent, add 1mol / L hydrochloric acid solution until the solution turns clear red, slowly add 1mol / L sodium hydroxide solution until the pH is between 9 and 10, and use a cloth The obtained solid was washed three times with 50 mL of distilled water, and dried with an infrared lamp to obtain 3.40 g of a pink solid with a yield of 75.0%.

[0061] (2) Synthesis of Intermediate 2

[0062] Intermediate 1 (1.36g, 2.5mmol) was dissolved in 30mL of dichloromethane, sti...

Embodiment 3

[0068] The synthesis of a kind of organic small molecule probe (I) of the present embodiment, concrete synthetic steps are as follows:

[0069] (1) Synthesis of Intermediate 1

[0070] Rhodamine B (4.80g, 10mmol) was added to a 250mL three-necked flask, 100mL of ethanol was added, vigorously stirred at room temperature for 5 minutes, and excess hydrazine hydrate monohydrate (12mL, 197mmol) was slowly added dropwise, then the reaction was heated to 80 React at ℃ for 4 hours. After the reaction is complete, spin dry the solvent, add 1mol / L hydrochloric acid solution until the solution turns clear red, slowly add 1mol / L sodium hydroxide solution until the pH is between 9 and 10, and use a cloth The obtained solid was washed three times with 50 mL of distilled water, and dried with an infrared lamp to obtain 3.40 g of a pink solid with a yield of 75.0%.

[0071] (2) Synthesis of Intermediate 2

[0072] Intermediate 1 (1.36g, 2.5mmol) was dissolved in 30mL of dichloromethane, sti...

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Abstract

The invention belongs to the technical field of transition metal detection and discloses a fluorescence probe for detecting three-valent iron ions and a preparation method of the fluorescence probe. The structural formula of the fluorescence probe is represented by a formula (I) (shown in the description). The preparation method comprises the following steps: reacting by virtue of rhodamine B andhydrazine hydrate in an ethanol solution, so as to obtain an intermediate 1; reacting by virtue of the intermediate 1 with chloroacetyl chloride and triethylamine in dichloromethane under an ice bathcondition, so as to obtain an intermediate 2; and adding potassium iodide, 2-methoxy-benzylamine or 2-thienylmethylamine and potassium carbonate into acetonitrile for reaction, so as to obtain a fluorescence probe for detecting Fe<2+>. The preparation method only comprises the three steps, the after-treatment process is simple, the operation is simple, and the product is easily prepared; and the prepared product can be applied to ultraviolet and fluorescent double response reaction detection of Fe<3+> and can be used for detecting Fe<3+> through naked eyes; and the preparation method has the advantages of high response speed and sensitivity and has wide application prospects in the fields of chemical engineering, environment, biological medicines and the like.

Description

technical field [0001] The invention belongs to the technical field of transition metal detection, and in particular relates to a fluorescent probe for detecting ferric ions and a preparation method thereof. Background technique [0002] Iron is a metallic element with atomic number 26. Pure iron is a silver-white metal with good flexibility and ductility. It is used to make iron cores of generators and motors. Iron and its compounds are also used to make magnets, medicines, inks, pigments, abrasives, etc. One of the "black metal". Iron is an essential element in biological systems, indispensable to all living systems, and widely distributed in the environment and organisms. In living organisms, Fe 3+ Plays a key role in many physiological processes, such as cell metabolism, oxygen transport, enzymatic reactions, and protein transport, while Fe 3+ The lack or excessive accumulation of nutrient will cause various health problems in the organism, such as heart disease, can...

Claims

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Application Information

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IPC IPC(8): C07D491/052C09K11/06G01N21/64
CPCC07D491/052C09K11/06C09K2211/1029C09K2211/1088C09K2211/1092G01N21/643G01N21/6447
Inventor 颜金武张雷吴紫盈李晶
Owner SOUTH CHINA UNIV OF TECH
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