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Preparation method and application of sodium tetraphenylethylene disulfonate

A technology of sodium bissulfonate and tetraphenylethylene, which is applied in the field of protein detection and sodium tetrastyryl disulfonate, can solve the problems of complex synthesis steps, poor water solubility, high cost, etc., and achieve good water solubility and fluorescence intensity Effect of Enhanced, Good Aggregation-Induced Luminescent Properties

Inactive Publication Date: 2020-08-21
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still some problems with these fluorescent probes
For example, the poor water solubility, high background fluorescence signal in aqueous medium, complex synthesis steps, high cost and aggregation-induced quenching (ACQ) phenomenon greatly limit its practical application.

Method used

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  • Preparation method and application of sodium tetraphenylethylene disulfonate
  • Preparation method and application of sodium tetraphenylethylene disulfonate
  • Preparation method and application of sodium tetraphenylethylene disulfonate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: Preparation of TPE-diSS (tetrastyryl disulfonic acid sodium salt)

[0027] (1) Weigh 0.46g (2.5mmol) of benzophenone and 1.64g (25mmol) of zinc powder, add them to a 100mL two-necked round-bottomed flask equipped with a stirring magnet, and put a rubber Stopper, the other bottle mouth is connected with a double row tube, start vacuuming operation, and feed nitrogen, these two operations are repeated 3 times. Dissolve 0.54g (2.5mmol) of 4,4'-dihydroxybenzophenone in 37.5mL of anhydrous tetrahydrofuran and add it to a two-necked round-bottomed flask, mix ethyl acetate and liquid nitrogen to create a low-temperature environment, and keep the temperature at -10°C, slowly add 2.36g (12.5mmol) of TiCl dropwise under stirring condition 4 , remove the ice bath device, wait for the temperature to rise to room temperature, after reacting at room temperature for 0.5h, slowly raise the temperature to 75°C, and the reaction time is 12h. After the reaction was complet...

Embodiment 2

[0033] Embodiment 2: Optical property test of TPE-diSS

[0034] Configure 0.5mM TPE-diSS aqueous solution, measure its excitation spectrum and fluorescence emission spectrum, such as figure 2 As shown, the maximum excitation wavelength is at 365nm, and the molecule has a strong fluorescence emission peak at 485nm after being excited.

Embodiment 3

[0035] Example 3: Fluorescent detection of BSA in aqueous solution by TPE-diSS

[0036] A. Prepare TPE-diSS and BSA stock solutions with a concentration of 100 μM, add a series of BSA with different concentration gradients to the same amount of TPE-diSS solution, and dilute the concentration so that the final concentration of TPE-diSS is 5 μM, and the concentration of BSA The concentrations were 0.005 μM, 0.01 μM, 0.05 μM, 0.1 μM, 0.5 μM, 1.0 μM, 5.0 μM, 10 μM and 50 μM, respectively. At an excitation wavelength of 350 nm, the fluorescence emission spectrum of the TPE-diSS solution was recorded. Such as image 3 As shown, the fluorescence intensity gradually increases with the increase of BSA concentration, and the maximum emission wavelength shows a slight blue shift, which may be due to the intermolecular interaction force between TPE-diSS and BSA.

[0037] B. Record the emission wavelength intensity at 474nm, and the linear fitting curve, such as Figure 4 ,5 As shown, w...

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Abstract

The invention discloses a preparation method and an application of sodium tetraphenylethylene disulfonate, and belongs to the technical field of organic fluorescent molecules. The structural formula of the sodium tetraphenylethylene disulfonate is represented by formula (I). The preparation method comprises the following two steps: (1) carrying out a McMurry reaction on 4,4'-dihydroxy benzophenoneand benzophenone to obtain an intermediate; and (2) salifying the intermediate obtained in step (1) to obtain the sodium tetraphenylethylene disulfonate. The sodium tetraphenylethylene disulfonate provided by the invention has good fluorescence property and water solubility, and can be used as a novel fluorescent probe for detecting protein.

Description

technical field [0001] The invention belongs to the technical field of organic fluorescent molecules, and in particular relates to sodium tetrastyryl bissulfonic acid, its preparation method, and its application in protein detection. Background technique [0002] Protein provides the human body with amino acids and energy necessary for life activities, and plays an important role in food safety, medical diagnosis and bioengineering research, and it is particularly important for the detection of specific proteins. At present, the commonly used protein detection methods mainly include Kjeldahl method, colorimetric method, gel electrophoresis method, high performance liquid chromatography and so on. Although the above method has been used for a long time, there are still many deficiencies. For example, although colorimetry is simple and quick to operate, its sensitivity and accuracy are poor; high-performance liquid chromatography has relatively high detection sensitivity, but...

Claims

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Application Information

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IPC IPC(8): C07C303/32C07C309/11C09K11/06G01N21/64
CPCC07C303/32C07C309/11C09K11/06C09K2211/1007G01N21/6428G01N2021/6432
Inventor 张丽娟杨云帆吕超管伟江
Owner BEIJING UNIV OF CHEM TECH
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