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Polystyrene high-fluorescence microsphere and preparation method thereof

A technology of polystyrene microspheres and polystyrene, applied in the field of fluorescent microspheres, can solve problems such as easy aggregation, achieve high fluorescence quantum yield, weak interaction, and not easy to aggregate

Active Publication Date: 2020-04-24
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 in the prior art that the conjugated fluorescent molecules in the polystyrene fluorescent microspheres added with organic conjugated fluorescent molecules are easy to aggregate and produce fluorescence quenching under high addition amount, and the fluorescence emission range is wide. A kind of polystyrene high fluorescence microsphere and preparation method thereof

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] A kind of preparation method of 1,7-vinyl-perylene imide derivative is as follows:

[0037] Insertion method of bulky substituent at imide position:

[0038] 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.

[0039] The access method of the double bond substituent at the bay position:

[0040] Take 1,7-Br-PDI-X (77.4mg, 0.10mmol) in a 50mL eggplant-shaped flask, add HP...

Embodiment 2

[0043] A kind of preparation method of 1,7-vinyl-perylene imide derivative is as follows:

[0044] Insertion method of bulky substituent at imide position:

[0045] 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.

[0046] The access method of the double bond substituent at the bay position:

[0047] Take 1,7-Br-PDI-X (77.4mg, 0.10mmol) in a 50mL eggplant-shaped flask, add HPLC grade THF (20m...

Embodiment 3

[0050] A kind of preparation method of 1,7-vinyl-perylene imide derivative is as follows:

[0051] Insertion method of bulky substituent at imide position:

[0052] 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.

[0053] The access method of the double bond substituent at the bay position:

[0054] 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 polystyrene high-fluorescence microsphere and a preparation method thereof, according to the invention, a 1, 7-vinyl-perylene bisimide derivative is used as a cross-linkingagent, and the microsphere has fluorescence. The imide site of the 1, 7-vinyl-perylene bisimide derivative has a large-volume substituent, so that molecules are not easy to aggregate, and fluorescenceis not easy to quench. When the fluorescent microsphere is prepared through suspension polymerization, a good solvent of the 1, 7-vinyl-perylene bisimide derivative is added, and the 1, 7-vinyl-perylene bisimide derivative is further dispersed in suspension droplets in a monomolecular state through the good solvent. Polymerization is initiated to form polystyrene microspheres with 1, 7-vinyl-perylene bisimide derivative imide as a cross-linking point, and the cross-linking point is uniformly distributed in a monomolecular form. The 1, 7-vinyl-perylene bisimide derivative imide aggregation fluorescence quenching phenomenon in the fluorescent microspheres is effectively avoided, the fluorescence quantum yield is high, and the fluorescence emission wavelength distribution is narrow.

Description

technical field [0001] The invention belongs to the technical field of fluorescent microspheres, and relates to a polystyrene high-fluorescence microsphere and a preparation method thereof, in particular to a polystyrene high-fluorescence microsphere whose fluorescence is not easily quenched and a preparation method thereof. Background technique [0002] Fluorescent microspheres refer to the microspheres that use chemical or physical preparation methods to load fluorescent substances in carrier microspheres, which can emit fluorescence after being induced by external energy. Fluorescent microspheres are a kind of functional microspheres, which are widely used in signal transmission, imaging, analysis and detection of biomolecules. [0003] The preparation methods of polystyrene fluorescent microspheres usually have the following types: (1) physical adsorption method (dyeing method, swelling method), this type of method is suitable for loading hydrophobic fluorescent dyes int...

Claims

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Application Information

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IPC IPC(8): C08F212/08C08F230/08C09K11/06C08F2/18
CPCC08F212/08C09K11/06C08F2/18C09K2211/1491C09K2211/145C09K2211/1416C08F230/08
Inventor 程建良孙宾顾洪达朱美芳顾益明陈珈胡余宗
Owner CHANGSHU POLYESTER
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