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A kind of preparation method of fluorescent polymer with hydrophilic shell and hydrophobic core structure

A fluorescent polymer, core structure technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of unclear degradation mechanism of inorganic quantum dots, decrease in fluorescence intensity, influence detection results, etc. Effects of bleaching and poor stability, increasing fluorescence intensity, and reducing photobleaching

Inactive Publication Date: 2011-12-07
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

The problem with this type of probe is that due to photobleaching, the fluorescence intensity of the fluorescent molecules decreases significantly or even completely fails after a period of light irradiation, which seriously affects the detection results.
However, there are strong interactions between polyelectrolytes and biomolecules, which will affect the detection results
Scientists have also developed inorganic quantum dots as fluorescent probes in recent years. This type of material can effectively solve the problems of photobleaching and stability, but the inorganic quantum dots that make up the light contain elements such as cadmium, tellurium, and arsenic, which are quite toxic and must be used Its surface undergoes many chemical modifications to improve its biocompatibility, and the steps are cumbersome
Moreover, the degradation mechanism of inorganic quantum dots in the body is still unclear. Whether the metal ions in them will be released when they exist in the body for a long time remains to be further studied.

Method used

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  • A kind of preparation method of fluorescent polymer with hydrophilic shell and hydrophobic core structure
  • A kind of preparation method of fluorescent polymer with hydrophilic shell and hydrophobic core structure
  • A kind of preparation method of fluorescent polymer with hydrophilic shell and hydrophobic core structure

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[0021] The invention discloses a method for preparing a fluorescent polymer with a hydrophilic shell and a hydrophobic core structure. The preparation method includes the following steps: (1) A hyperbranched fluorescent polymer is prepared by cyclotrimerization of a diacetylene monomer containing a fluorescent chromophore, and the periphery of the hyperbranched fluorescent polymer has unreacted alkynyl groups; Hydrophilic polymer segments with monofunctional groups can be substituted or coupled to obtain hydrophilic polymer segments that can be added or coupled, or hydrophilic monomers can be polymerized to obtain addition or coupleable hydrophilic Polymer segment; (2) the hyperbranched fluorescent polymer and the hydrophilic polymer segment that can be added or coupled are correspondingly added or coupled to obtain fluorescent polymerization of a hydrophilic shell and a hydrophobic core structure Things.

[0022] The fluorescent polymer obtained by the invention has a core-shel...

Embodiment 1

[0025] Step 1): On the one hand, 36 mL of N,N'-dimethylformamide (DMF) is added to a 100 mL flask. In an ice bath at 0°C, 46 mL of phosphorus oxychloride was added dropwise to the flask with constant stirring. After the addition of phosphorus oxychloride is completed, weigh 4.9 g of triphenylamine and add, remove the ice bath, and raise the temperature to 95°C. After 4 hours of refluxing reaction, extraction treatment, separation and purification by column chromatography, intermediate product 1 was obtained. Add 1.2 g of Intermediate Product 1 to a dry 250 mL two-necked flask to ensure anhydrous and oxygen-free conditions, and add 40 mL of dewatered tetrahydrofuran solution. Under ice bath, add 20 mL 0.5M acetylene magnesium bromide solution in tetrahydrofuran dropwise. The reaction was carried out overnight at room temperature, and the reaction was terminated with saturated aqueous ammonium chloride solution. After the reaction solution was extracted, the organic phase was ...

Embodiment 2

[0035] Step 1): Prepare hb-TPA according to the method of Example 1.

[0036] And the molecular weight 350 in Example 1 polyethylene glycol (PEG 350 -OH) is replaced by polyethylene glycol (PEG 1900 -OH), other preparation conditions are the same as in Example 1, and a polyethylene glycol (PEG) with a molecular weight of 1900 with a single azide end group was prepared 1900 -N 3 ).

[0037] Step 2): Weigh 40mg hb-TPA and 800mg PEG 1900 -N 3 In the polymerization tube, add 1 mL each of DMF and toluene as a solvent, and react at 100°C for 4 hours, so that the hb-TPA has unreacted alkynyl groups and PEG 1900 -N 3 1,3-dipolar cycloaddition reaction between the azido groups. After the reaction is completed, the reaction solution is diluted and precipitated in a large amount of n-hexane, allowed to stand for 24 hours, filtered and dried to constant weight to obtain an amphiphilic hyperbranched fluorescent polymer, that is, a fluorescent polymer with a hydrophilic shell and a hydrophobic co...

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Abstract

The invention discloses a method for preparing a fluorescent polymer with a hydrophilic shell and a hydrophobic core structure, which mainly includes the following steps: (1) preparing a hyperbranched fluorescent polymer through a cyclotrimerization reaction of a diacetylenic monomer containing a fluorescent chromophore Polymer, the periphery of the hyperbranched fluorescent polymer has unreacted alkynyl groups; the hydrophilic polymer segment with a single functional group is subjected to a substitution reaction to obtain an additive or coupleable hydrophilic polymer segment, or The hydrophilic monomer is polymerized to obtain an additive or coupleable hydrophilic polymer segment; (2) the hyperbranched fluorescent polymer is combined with an additive or coupleable hydrophilic polymer chain Correspondingly, the fluorescent polymer with hydrophilic shell and hydrophobic core structure can be obtained through addition or coupling reaction. The invention belongs to the technical field of functional materials. Compared with the prior art, the hydrophilicity is significantly improved; the defects of photobleaching and poor stability of small molecular organic fluorescent dyes are overcome; and the detection result is accurate.

Description

Technical field [0001] The invention belongs to the technical field of functional materials, and specifically relates to a method for preparing an amphiphilic fluorescent polymer. Background technique [0002] Fluorescence detection has the advantages of high sensitivity, high selectivity, fast response and non-destructiveness. More and more disciplines have begun to use fluorescence detection methods for scientific research, some of which have already been applied in practice. Especially in biomedicine, fluorescence detection has broad application prospects. Such as the detection of glucose in human blood, the process of metabolism in life activities, the hydrolysis of ATP, the identification of DNA, clinical analysis and other biochemical processes require a highly sensitive and easy-to-operate tool to achieve, made of fluorescent materials The fluorescent probe is undoubtedly one of the best choices. However, to be used in the biological field, the two key issues of water so...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G65/48C08G81/00G01N21/64C09K11/06C08G61/00
Inventor 唐莉孙景志秦安军唐本忠闫继明汪剑毛宇沈晓源梅菊
Owner ZHEJIANG UNIV
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