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Novel rhodamine fluorescent probe for detecting mercury ions, and preparation method of novel rhodamine fluorescent probe

A technology of fluorescent probes and mercury ions, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems that the structure of rhodamine fluorescent probes has not been disclosed, and achieve easy purification, high yield, and reaction short time effect

Inactive Publication Date: 2016-06-15
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Some rhodamine fluorescent probes and their application in mercury ion detection have been reported, such as CN104530064A and CN104479671A, but the rhodamine fluorescent probe structure as shown in the present invention is not disclosed

Method used

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  • Novel rhodamine fluorescent probe for detecting mercury ions, and preparation method of novel rhodamine fluorescent probe
  • Novel rhodamine fluorescent probe for detecting mercury ions, and preparation method of novel rhodamine fluorescent probe
  • Novel rhodamine fluorescent probe for detecting mercury ions, and preparation method of novel rhodamine fluorescent probe

Examples

Experimental program
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Effect test

Embodiment 1

[0038] The preparation of the fluorescent probe molecule rhodamine B derivative R, the specific route is shown in the following formula.

[0039]

[0040] The flow formula of the synthetic rhodamine B derivative R of the present invention

[0041] (1) Preparation of rhodamine B hydrazide

[0042] Add rhodamine B (4.79g, 0.01mol, 5mL 80% hydrazine hydrate, 30mL ethanol) into a 50mL round bottom flask, stir and reflux the mixed solution for 4-5h, add water to precipitate the solid after cooling, obtain the crude product by filtration, dry it with ethyl acetate / petroleum ether recrystallization to obtain a light pink powder solid, i.e. rhodamine B hydrazide, with a yield of 92%.

[0043] (2) Preparation of Schiff base

[0044] Add rhodamine B hydrazide (2.28g, 0.005mol), phenylglyoxal monohydrate (1.02g, 0.006mol) and 30mL of anhydrous methanol into a 25mL round bottom flask, stir and reflux for 3h, filter and dry to obtain Fu base, yield 95%. Its H NMR spectrum ( 1 HNMR...

Embodiment 2

[0048] Fluorescence Spectrum Changes of Rhodamine B Derivative R with Different Alcohol / Water Ratio

[0049] The rhodamine B derivative R prepared in Example 1 was dissolved in ethanol to prepare a 100 μM stock solution. Prepare 10 μM fluorescent probe solutions with different ratios of ethanol and water, and add 0.5 equivalent of mercury ions in sequence, the fluorescence intensity of the solution changes as follows: Figure 7 shown. from Figure 7 It can be seen that the fluorescence intensity of the solution increases gradually with the increase of the alcohol / water ratio, but when the alcohol / water ratio is greater than 6:4, the enhancement of the fluorescence intensity of the solution tends to be gentle. Therefore, the alcohol / water ratio of 6:4 is the best test condition.

Embodiment 3

[0051] Changes of Fluorescence Spectrum of Rhodamine B Derivative R at Different pH

[0052] The stock solution prepared in Example 2 was used to prepare 10 μM fluorescent probe solutions with different pHs, and the fluorescence intensity of the solutions changed as follows: Figure 8 shown. from Figure 8 It can be seen that in the range of pH<6, with the increase of acidity, the fluorescence intensity is obviously enhanced; in the range of pH6-9, the fluorescence intensity is basically constant, indicating that the probe is suitable for testing under biological environmental conditions.

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Abstract

The invention relates to a novel rhodamine fluorescent probe for detecting mercury ions, and a preparation method of the novel rhodamine fluorescent probe, belonging to the technical fields of fluorescent probes and preparation methods of the fluorescent probes. The invention discloses a structure of the rhodamine fluorescent probe. The invention also discloses the preparation method of the rhodamine fluorescent probe; the preparation method comprises the steps of enabling rhodamine B and hydrazine hydrate to have a reflux reaction in ethanol to generate rhodamine hydrazide; after that, enabling the generated rhodamine hydrazide and phenyl glyoxal to have a reflux reaction in ethanol, and carrying out recrystallization to obtain Schiff base; reducing the Schiff base by sodium borohydride to generate the fluorescent probe. The fluorescent probe provided by the invention is simple in synthesis steps, high in yield, good in selectivity for the mercury ions and short in response time, can work under the physiological environment condition, and has prospect of being applied to bioluminescent imaging.

Description

technical field [0001] The invention relates to a rhodamine fluorescent probe for detecting mercury ions and a preparation method thereof, and belongs to the technical field of fluorescent probes and preparation methods thereof. Background technique [0002] Mercury ion is a typical heavy metal ion with strong toxicity. Once mercury ions enter the water environment, they will be converted into organic methylmercury by bacterial microorganisms, and quickly accumulate in organisms (such as fish) to enter the food chain. Methylmercury damages the human nervous system, causing brain damage, cognitive and motor disorders, etc. Minamata disease, which shocked the world, is a type of organic mercury poisoning. Therefore, it is of great significance to find a method that can quickly and accurately detect mercury ions. [0003] Rhodamine-based fluorescent dyes have excellent photophysical and photochemical properties such as good photostability, long-wavelength red light emission, ...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D491/107G01N21/64
CPCC07D491/107C09K11/06C09K2211/1029C09K2211/1088G01N21/6428G01N21/6486
Inventor 吴向阳肖慧丰张海燕刘杰张敏仰榴青
Owner JIANGSU UNIV
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