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Selenium-containing macromolecular fluorescent probe and preparation method thereof

A technology of fluorescent probes and macromolecules, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of selenium-containing small molecule fluorescent probes such as water solubility and poor stability

Active Publication Date: 2019-04-26
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, selenium-containing small molecule fluorescent probes have the disadvantages of water solubility and poor stability.
However, the research on selenium-containing macromolecular fluorescent probes has not been reported yet.

Method used

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  • Selenium-containing macromolecular fluorescent probe and preparation method thereof
  • Selenium-containing macromolecular fluorescent probe and preparation method thereof
  • Selenium-containing macromolecular fluorescent probe and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] (1) Synthesis of sodium diselenide:

[0052] Add NaOH (0.4mol) into a 500ml three-neck flask, add 150ml of water to dissolve it, add selenium powder (0.4mol) and tetrabutylammonium bromide (2.5mmol) under stirring to obtain a reaction solution. Add sodium borohydride (0.85mol) and sodium hydroxide (0.04mol) into the beaker, add 5ml of water to dissolve them, and add them to the above reaction solution in batches, after the addition, react at room temperature for 1h, Then the temperature was raised to 90°C for 0.5h. Pour the reaction solution into a 500ml beaker, let it cool naturally and place it in the refrigerator, filter the precipitated solid with suction, wash it with acetone and ether in turn, and the reddish-brown needle-like solid obtained is the product sodium diselenide. The reaction scheme of above-mentioned reaction is as follows:

[0053]

[0054] (2) Synthesis of 2,2'-dialdehyde diphenyl diselenide

[0055] First, the 50ml three-necked flask was vent...

Embodiment 2

[0069] Steps (1)-(3) are the same as in Example 1.

[0070] (4) Weigh Se-BODIPY (0.2mmol) into a 5ml ampoule at room temperature, add PEGMA 500 (Molecular weight is 500g / mol, 12.0mmol), refrigerated and pumped three times, sealed after deoxygenation, stirred and reacted under a high-pressure mercury lamp for 48h, and ended the reaction. Dissolve in 1ml tetrahydrofuran, precipitate with ether, centrifuge to obtain the polymer, put it in a vacuum oven for drying, and obtain a selenium-containing macromolecular fluorescent probe, which is named PPEGMA 500 . The reaction scheme diagram of above reaction is as follows, wherein, n=280:

[0071]

[0072] Figure 8 for PPEGMA 500 It can be seen that there is an obvious signal peak at 2.58ppm, which belongs to the methyl peak after Se-BODIPY participates in the polymerization; there is a signal peak at 5.99ppm, which belongs to the pyrrole after Se-BODIPY participates in the polymerization. The hydrogen signal peaks at 7.06-7.2...

Embodiment 3

[0077] The 50ml three-necked flask was ventilated with argon for ten minutes, and the air was removed. Then, o-bromobenzaldehyde (20mmol), sodium diselenide (40mmol) synthesized in Example 1 was added in the 50mL three-necked flask, and 20mL tetrahydrofuran was added as a solvent to keep the air Argon, after stirring at room temperature for 2h, the temperature was raised to 90°C and the reaction was refluxed for 40h. After natural cooling, wash with water and extract with ethyl acetate (20mL×3 times), take the organic phase and dry it with anhydrous sodium sulfate, rotary evaporate, remove the solvent and then separate by silica gel column chromatography (eluent PE:EA=3:1 ) to obtain a yellow solid, which is the product 2,2'-dialdehyde diphenyl diselenide.

[0078] The three-necked flask was vented with argon for two hours, and the air was removed. Then, 2,2'-dialdehyde diphenyl diselenide (1 mmol) was added to a 50-ml three-necked flask, 25 ml of dry dichloromethane was added...

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Abstract

The invention relates to a preparation method for a selenium-containing macromolecule fluorescence probe. The method comprises the following steps: enabling o-position halogenated benzaldehyde and sodium diselenide to react in an organic solvent at 90-120 DEG C, thereby acquiring 2,2'-diphenyl diselenide; enabling 2,2'-diphenyl diselenide to react with 2,4-dimethyl pyrrole under an effect of catalyst, adding an oxidizing agent for continuing reacting, adding organic alkali and a complexing agent and reacting at 20-40 DEG C, thereby acquiring 2,2'-difluoro boron pyrrole diphenyl diselenide; performing free radical polymerization reaction on 2,2'-difluoro boron pyrrole diphenyl diselenide and a compound containing double bond at 20-70 DEG C, thereby acquiring the selenium-containing macromolecule fluorescence probe. The invention also discloses the selenium-containing macromolecule fluorescence probe prepared according to the method. According to the method provided by the invention, the selenium-containing diselenide is firstly prepared and then is utilized to regulate the polymerization of monomer, so that the selenium-containing macromolecule fluorescence probe can be acquired. The selenium-containing macromolecule fluorescence probe can be used for detecting oxides.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to a selenium-containing macromolecular fluorescent probe and a preparation method thereof. Background technique [0002] During the process of aerobic respiration, organisms will produce a variety of active oxygen free radicals, which will produce corresponding physiological and pathological effects. Within a controllable range, active oxygen free radicals can interact with reduced substances to regulate cell signal transmission. If the content of these active oxygen free radicals is out of control, it will cause damage to proteins, lipids, and nucleic acids, and may cause various diseases. Due to the short half-life of active oxygen free radicals, the concentration in physical strength is very low, so real-time detection of the level of active oxygen free radicals in biological systems has become the research focus of scientists. The fluorescence detection method of rea...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F112/08C08F120/28C09K11/06G01N21/64
CPCC08F112/08C08F120/28C09K11/06C09K2211/1491G01N21/6428
Inventor 朱健刘倩李娜潘向强朱秀林
Owner SUZHOU UNIV
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