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Sulfonic acid functionalized polystyrene high-fluorescence microsphere and preparation method thereof

A polystyrene and sulfonic acid functional technology, which is applied in the field of sulfonic acid functionalized polystyrene high fluorescent microspheres and its preparation, can solve problems such as easy quenching, achieve weak interaction, strong fluorescence intensity, and not easy Aggregated effect

Active Publication Date: 2020-04-17
CHANGSHU POLYESTER +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The present invention aims to solve the technical problems of self-polymerization and easy quenching of fluorescence in divinylbenzene of polystyrene fluorescent microspheres in the prior art, and provides a sulfonic acid-functionalized polystyrene high-fluorescence microsphere and its preparation method

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] A kind of preparation method of 1,7-vinyl-perylene imide derivative is as follows:

[0046] Insertion method of bulky substituent at imide position:

[0047] Add crude product PTCDA-Br in 250mL three-necked flask (0.50g, 0.91mmol) and 1-methyl-2-pyrrolidone (NMP) 15.00mL and the solid was dissolved and stirred at 25°C for 1h. Then add 2-ethylhexylamine (4.5mmol), glacial acetic acid (16mL, 140mmol). Under the protection of nitrogen, the temperature was raised to 85°C, and the reaction was continued for 7h. After the reaction was completed, it was cooled to room temperature, and then 120.00 mL of methanol was added thereto and stirred overnight. After suction filtration, a red solid was obtained, which was dried in vacuum for 24 hours at 85°C, and 1,7-Br-PDI-X was obtained after column chromatography.

[0048] The access method of the double bond substituent at the bay position:

[0049] Take 1,7-Br-PDI-X (77.4mg, 0.10mmol) in a 50mL eggplant-shaped flask, add HP...

Embodiment 2

[0052] A kind of preparation method of 1,7-vinyl-perylene imide derivative is as follows:

[0053] Insertion method of bulky substituent at imide position:

[0054] Add crude product PTCDA-Br in 250mL three-necked flask (0.50g, 0.91mmol) and 1-methyl-2-pyrrolidone (NMP) 15.00mL and the solid was dissolved and stirred at 25°C for 1h. then join (4.5mmol), glacial acetic acid (16mL, 140mmol). Under the protection of nitrogen, the temperature was raised to 85°C, and the reaction was continued for 7h. After the reaction was completed, it was cooled to room temperature, and then 120.00 mL of methanol was added thereto and stirred overnight. After suction filtration, a red solid was obtained, which was dried in vacuum for 24 hours at 85°C, and 1,7-Br-PDI-X was obtained after column chromatography.

[0055] The access method of the double bond substituent at the bay position:

[0056] Take 1,7-Br-PDI-X (77.4mg, 0.10mmol) in a 50mL eggplant-shaped flask, add HPLC grade THF (20m...

Embodiment 3

[0059] A kind of preparation method of 1,7-vinyl-perylene imide derivative is as follows:

[0060] Insertion method of bulky substituent at imide position:

[0061] Add crude product PTCDA-Br in 250mL three-necked flask (0.50g, 0.91mmol) and 1-methyl-2-pyrrolidone (NMP) 15.00mL and the solid was dissolved and stirred at 25°C for 1h. Then add 2-ethylhexylamine (4.5mmol), glacial acetic acid (16mL, 140mmol). Under the protection of nitrogen, the temperature was raised to 85°C, and the reaction was continued for 7h. After the reaction was completed, it was cooled to room temperature, and then 120.00 mL of methanol was added thereto and stirred overnight. After suction filtration, a red solid was obtained, which was dried in vacuum for 24 hours at 85°C, and 1,7-Br-PDI-X was obtained after column chromatography.

[0062] The access method of the double bond substituent at the bay position:

[0063] Take 1,7-Br-PDI-X (77.4mg, 0.10mmol) in a 50mL eggplant-shaped flask, add HP...

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Abstract

The invention relates to a sulfonic acid functionalized polystyrene high-fluorescence microsphere and a preparation method thereof. According to the invention, a cross-linking agent used for preparingthe microsphere is a 1,7-vinyl-perylene bisimide derivative, and the imide site of the cross-linking agent has a large-volume substituent group, so the molecule of the cross-linking agent is not easyto aggregate and is thus prevented from the phenomenon of self-polymerization. Meanwhile, the 1,7-vinyl-perylene bisimide derivative has a fluorescent chromophoric group; due to the fact that aggregation is limited by the large-volume substituent group and movement of the 1,7-vinyl-perylene bisimide derivative is limited by a cross-linking structure in the microsphere, fluorescence quenching caused by molecule aggregation is avoided, and the microsphere eventually has high fluorescence performance. The method successfully solves the problem that gel type polystyrene ion exchange resin is prone to poisoning, overcomes the phenomenon of high probability of self-polymerization of divinylbenzene when the gel type polystyrene ion exchange resin is prepared in the prior art, and enables the microsphere to have high fluorescence property.

Description

technical field [0001] The invention belongs to the technical field of gel-type ion exchange resins, and relates to a sulfonic acid-functionalized polystyrene high-fluorescence microsphere and a preparation method thereof, in particular to a sulfonic acid-functionalized microsphere that is not easy to self-polymerize and hard to quench Polystyrene high fluorescent microspheres and preparation method thereof. Background technique [0002] There is a serious shortcoming of gel-type ion exchange resin, which will produce "poisoning" phenomenon during use. It refers to the phenomenon that the ion exchange function will be lost after being used for a period of time. The research results show that if styrene and divinylbenzene are regarded as two monomers during copolymerization, because of the copolymerization characteristics of styrene and divinylbenzene, the self-polymerization rate of divinylbenzene is higher than that of styrene copolymerization during the copolymerization p...

Claims

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Application Information

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IPC IPC(8): C08F8/36C08F212/08C08F212/34C08F230/08
CPCC08F8/36C08F212/08C08F212/34C08F230/08
Inventor 顾洪达孙宾徐雪刚朱美芳龚建德侯萨姆王慧
Owner CHANGSHU POLYESTER
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