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Preparation and application of a temperature-sensitive dual-fluorescent PDOTs based on single-arm TPE molecules

A temperature-sensitive, dual-fluorescence technology used in the field of biochemistry to solve problems such as less work

Active Publication Date: 2021-06-08
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there are very few works on the application of two-color fluorescent polymer quantum dots with AIE properties in fluorescence imaging

Method used

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  • Preparation and application of a temperature-sensitive dual-fluorescent PDOTs based on single-arm TPE molecules
  • Preparation and application of a temperature-sensitive dual-fluorescent PDOTs based on single-arm TPE molecules
  • Preparation and application of a temperature-sensitive dual-fluorescent PDOTs based on single-arm TPE molecules

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] 1) Preparation of monohydroxytetraphenylethylene (TPE-OH):

[0050] Dissolve 0.05 mol of 4-hydroxybenzophenone, 0.1 mol of Zn powder, and 0.05 mol of benzophenone in 150.0 mL of anhydrous THF, stir under a nitrogen atmosphere, and vacuumize for 30 min to keep the system dry and free of water. oxygen. Then slowly drop 0.27mol TiCl 4 , reacted in an ice bath for 30 min, and refluxed at 70 °C for 24 h under an argon atmosphere. After the reaction, the reactant was cooled to room temperature and injected with 10% K 2 CO 3 Aqueous solution quenched the reaction. After vacuum filtration with a sand core funnel paved with silica gel, the filtrate was obtained and extracted with ethyl acetate to separate the organic layer. Ethyl acetate was removed by rotary evaporation, and the resulting crude product was separated and purified by column chromatography (eluent: V 乙酸乙酯 :V 石油醚 =1:10) to obtain the initiator TPE-OH, vacuum-dried, the yield was 40%.

[0051] 2) Preparation...

Embodiment 2

[0065] According to the molar ratio of 1:2, take 4-hydroxybenzophenone and benzophenone respectively, and then take zinc powder and TiCl 4 , the molar weight of the zinc powder taken is 1.5 times the total molar weight of both the 4-hydroxybenzophenone and the benzophenone taken, and the TiCl 4The molar weight is 3 times of the total molar weight of 4-hydroxybenzophenone and benzophenone; 4-hydroxybenzophenone, benzophenone and zinc powder are dissolved in anhydrous tetrahydrofuran, Stir under a nitrogen atmosphere, vacuumize and circulate for 30 min to keep the system anhydrous and oxygen-free, then slowly add TiCl dropwise 4 , reacted in an ice bath for 30 min, under argon atmosphere, refluxed at 70 °C for 24 h; after the reaction was completed, cooled to room temperature, and added K with a mass fraction of 10% 2 CO 3 Aqueous solution, quenching reaction, extraction with ethyl acetate, rotary evaporation drying, obtains white crude product; Crude product crosses silica ge...

Embodiment 3

[0067] According to the molar ratio of 1:1.5, take 4-hydroxybenzophenone and benzophenone respectively, and then take zinc powder and TiCl 4 , the molar weight of the zinc powder taken is 1.25 times the total molar weight of both the 4-hydroxybenzophenone and the benzophenone taken, and the TiCl 4 The molar weight is 2.5 times of the total molar weight of 4-hydroxybenzophenone and benzophenone; 4-hydroxybenzophenone, benzophenone and zinc powder are dissolved in anhydrous tetrahydrofuran (without water THF), stirred under a nitrogen atmosphere, vacuum cycled for 30 min to keep the system anhydrous and oxygen-free, and then slowly added TiCl dropwise 4 , reacted in an ice bath for 30 min, under argon atmosphere, refluxed at 72 °C for 24 h; after the reaction was completed, cooled to room temperature, and added K 2 CO 3 Aqueous solution, quenching reaction, extraction with ethyl acetate, rotary evaporation drying, obtains white crude product; Crude product crosses silica gel c...

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Abstract

The invention discloses the preparation and application of temperature-sensitive dual-fluorescent Pdots based on single-arm TPE molecules, using small organic molecules with AIE properties as fluorophores, and using polyε-caprolactone as a hydrophobic segment through a common free radical polymerization method , poly-N-isopropylacrylamide is covalently combined as a hydrophilic segment into an amphiphilic copolymer, and Eu(Ⅲ) ion is introduced for complexation and nanoprecipitation to prepare single-armed Pdots with tunable fluorescence emission. The single-arm Pdots prepared by the preparation method of the present invention are small balls with a particle diameter of about 6nm; they have AIE properties, dual fluorescent properties and temperature responsiveness, and are excellent temperature-sensitive dual fluorescent nanomaterials; the single-arm dual Fluorescent Pdots have low toxicity, are easier to be captured by Hela cells, have excellent imaging effects in Hela cells, and can be used as cell tracers in the biological field.

Description

technical field [0001] The invention belongs to the technical field of biochemistry, and relates to the preparation of a Pdots material, in particular to the preparation of a temperature-sensitive dual-fluorescence Pdots material based on a single-arm TPE molecule; the temperature-sensitive dual-fluorescence Pdots material of the single-arm TPE molecule is respectively Staining HepG2, A549, and Hela cells, compared with HepG2, A549 cells, Pdots are easier to be captured by Hela cells, and have excellent imaging effects in Hela cells, and can be used as cell tracers in the biological field. Background technique [0002] Nowadays, the rapid development of fluorescence imaging requires biological probes with stronger tissue penetration ability, lower biological toxicity, higher signal-to-noise ratio and better spatial and temporal resolution. However, most of the current fluorescence imaging bioprobes are monochromatic fluorescence. Since the excitation wavelength of monochroma...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F293/00C08F220/54C08F8/42C08G63/08C08J3/28C09K11/06G01N21/64C08L53/00
CPCC08F8/42C08F220/54C08F293/00C08G63/08C08J3/28C08J2353/00C09K11/06C09K2211/182G01N21/6486
Inventor 关晓琳王林杨学琴李志飞刘美娜王凯龙来守军
Owner NORTHWEST NORMAL UNIVERSITY