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Ratio type fluorescent molecular probe as well as preparation method and application thereof

A fluorescent molecular probe, ratiometric technology, applied in the field of ratiometric fluorescent molecular probes and its preparation, can solve the problems of low emission intensity, limited application of environmental detection, etc., achieve wide detection range, avoid self-absorption and biological background Fluorescence interference, the effect of cheap and easy-to-obtain raw materials

Active Publication Date: 2020-11-27
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, patent 201910141848.9 "A ratiometric fluorescent probe for detecting intracellular pH and its preparation method and application" discloses a ratiometric fluorescent probe based on hydroxyl-type ESIPT, which can realize rapid detection of intracellular pH, However, the emission intensity of its long-wavelength is much lower than that of short-wavelength, which greatly limits its application in environmental detection.

Method used

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  • Ratio type fluorescent molecular probe as well as preparation method and application thereof
  • Ratio type fluorescent molecular probe as well as preparation method and application thereof
  • Ratio type fluorescent molecular probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Synthesis of fluorescent probes

[0037] R in the fluorescent probe structural formula prepared in this embodiment 1 = Cl, R 2 =H.

[0038] The synthesis technique route of present embodiment is asfigure 1 As shown, it specifically includes the following steps:

[0039] Synthesis of compound 3

[0040] Weigh compound 1 5-chloroisatoic anhydride (1.96g, 10mmol) and place it in a 250mL round-bottomed flask, add 40mL of acetic acid, dissolve and add compound 2 o-aminothiophenol (1.25g, 10mmol) dropwise under stirring at room temperature, room temperature After stirring for 5 hours, during the reaction process, the reaction solution gradually changed from gray turbid liquid to light yellow clear liquid; TLC monitored the reaction process, and the dark spots of raw materials gradually decreased, and blue fluorescent spots with relatively less polarity appeared. After the reaction was completed, the reaction solution was poured into 200 mL of water, and a yellow-gray prec...

Embodiment 2

[0045] Solvent Effects of Fluorescent Probes

[0046] Weigh 4.15 mg of the fluorescent molecular probe prepared in Example 1 and dissolve it in 100 mL of various organic solvents (normal hexane, dichloromethane, tetrahydrofuran, acetonitrile, N,N-dimethylformamide, dimethyl sulfoxide , ethanol, methanol) to obtain fluorescent probe solutions with a concentration of 100 μM in different polar solvents. Use a light source with a wavelength of 360nm to excite, measure the fluorescence emission spectrum, and after normalization, the results are as follows image 3 shown.

[0047] In non-polar solvents, such as the longest fluorescence emission wavelength in n-hexane, the strongest emission wavelength is located at 565nm, and its large Stokes shift (205nm) shows that it is the imine emission of fluorescent molecular probes; while in polar In slightly larger dichloromethane, tetrahydrofuran, and ethanol, the strongest emission wavelength has a certain blue shift (the emission peaks...

Embodiment 3

[0049] Preparation of Fluorescent Probe Stock Solutions

[0050] Accurately weigh 83 mg of the fluorescent molecular probe prepared in Example 1, add it into a 100 mL volumetric flask, add dimethyl sulfoxide to make it fully dissolve and constant volume, shake well to obtain a probe stock solution with a concentration of 2 mM.

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Abstract

The invention discloses a ratio type fluorescent molecular probe as well as a preparation method and an application thereof, the structural formula of the ratio type fluorescent molecular probe is shown as a formula I. The preparation method of the ratio type fluorescent molecular probe for detecting the pH value is simple, raw materials are cheap and easy to obtain, the synthesis process is simple, the yield is high, and the ratio type fluorescent molecular probe is suitable for large-scale production, popularization and application. The fluorescent probe has excited state intramolecular proton transfer property, so that the interference of self-absorption and biological background fluorescence can be effectively avoided, and the error caused by non-uniform probe use concentration, non-uniform probe distribution and the like can be avoided due to ratio type response. In actual detection, the fluorescent probe is quick in response, wide in detection range and high in sensitivity, has high anti-interference performance on common coexisting substances in a sample, has good repeatability on detection of the pH value, and can realize repeated cyclic application by adjusting the pH value. The probe disclosed by the invention has a wide application prospect in the aspect of pH value detection in various scenes such as environmental samples, biological samples and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, analysis and detection, and specifically relates to a ratio-type fluorescent molecular probe and its preparation method and application. Background technique [0002] The pH of environmental samples is an important monitoring indicator. For example, the pH of rivers is usually between 6 and 8, while that of lake water is mainly between 7.2 and 8.5. When the pH of the water body deviates from the normal range, whether it is acidic or alkaline, the growth of aquatic organisms will be inhibited and the number will decrease, which will seriously affect the self-purification ability of the water body. Therefore, in the monitoring of environmental samples, the determination of the pH value is of great significance. In medicine and life sciences, pH also occupies an important position: as one of the important parameters of metabolism, it plays a key role in maintaining the normal growth, prol...

Claims

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Application Information

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IPC IPC(8): C07D277/66C09K11/06G01N21/64
CPCC07D277/66C09K11/06G01N21/6428C09K2211/1037C09K2211/1014G01N2021/6421G01N2021/6439
Inventor 曾文彬冯斌毕桉耀吴佳欣范多阳刘翊
Owner CENT SOUTH UNIV
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