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A fluorescent compound based on tetraphenylethylene and its preparation method and application

A technology of fluorescent compounds and tetraphenylethylene, which is applied in the preparation of organic compounds, chemical instruments and methods, preparation of carboxylates, etc., can solve the problems of limited application range, quenching, and weakening of fluorescence, and achieves good temperature responsiveness, Improve the effect of application scope and application environment

Active Publication Date: 2018-12-07
深圳尚诺生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Most of the traditional fluorescent compounds have high fluorescence quantum yield in dilute solution, but the fluorescence is weakened or even quenched in high concentration or in the state of aggregation. This aggregation-induced quenching effect greatly limits their application range.

Method used

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  • A fluorescent compound based on tetraphenylethylene and its preparation method and application
  • A fluorescent compound based on tetraphenylethylene and its preparation method and application
  • A fluorescent compound based on tetraphenylethylene and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0044] Synthesis of fluorescent compounds of the present invention

[0045] The preparation route of fluorescent material of the present invention is as follows:

[0046]

[0047] Dissolve 2 mmol of compound 1 in 10 mL of dichloromethane, add thionyl chloride, the ratio of the amount of thionyl chloride to compound 1 is 5:1, add a drop of N,N-dimethylformamide, heat After reflux for 4 hours, the volatile solvent was removed by rotary evaporation under reduced pressure to obtain an acid chloride intermediate, and then anhydrous dichloromethane was added to obtain a mixed solution. The mixed solution was slowly added dropwise to 5 mL of dichloromethane solution containing 1 mmol of glyceryl monostearate and 2 mmol of triethylamine, and stirred at room temperature for 48 hours. After the reaction was completed, saturated saline was added, and then extracted with ethyl acetate. After drying with anhydrous sodium sulfate for 2 hours, the solid sodium sulfate was removed by filt...

Embodiment 2

[0053] Preparation of temperature-sensitive fluorescent material with DSPC as the main raw material and the corresponding curve of fluorescence intensity versus temperature

[0054] Take 0.23mL of fluorescent compound I in chloroform, 2.0mL of DSPC in chloroform, and 0.125mL of DSPE-PEG2000 in chloroform in a 25mL round-bottomed flask, and spin evaporate for 30min under reduced pressure; then add 2.5mL of deionized water and place in a water bath Sonicate for 30 minutes and let it stand for 24 hours; take 0.2mL of nano-solution and dilute it to 2mL, measure the change of fluorescence intensity with temperature, and record the change of fluorescence intensity at 475nm with a fluorescence spectrometer. In the measurement of the change of fluorescence intensity with temperature in this embodiment, under the excitation of 325nm excitation light, the relationship diagram of the change of fluorescence intensity with temperature is as follows figure 2 shown.

Embodiment 3

[0056] Preparation of temperature-sensitive fluorescent material with DAPC as the main raw material and the corresponding curve of fluorescence intensity versus temperature

[0057] Take 0.23mL of compound I in chloroform, 1.89mL of DAPC in chloroform, and 0.125mL of DSPE-PEG2000 in chloroform in a 25mL round-bottomed flask, and rotate under reduced pressure for 30min; then add 2.5mL of deionized water, and ultrasonically 30min, stand still for 24 hours; dilute 0.2mL of nano-solution to 2mL, measure the change of fluorescence intensity with temperature, and record the change of fluorescence intensity at 475nm with a fluorescence spectrometer. In the measurement of the change of fluorescence intensity with temperature in this embodiment, under the excitation of 325nm excitation light, the relationship diagram of the change of fluorescence intensity with temperature is as follows image 3 shown.

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Abstract

The invention discloses a tetraphenyl ethylene based fluorescent compound as well as a preparation method and an application thereof. A structure of the fluorescent compound is represented as a formula (I). The fluorescent compound is prepared through steps as follows: tetraphenyl ethylene glycollic acid is taken as a raw material and subjected to condensation with glycerin monostearate, then an obtained reaction product reacts with succinic anhydride and subjected to ring opening, and the fluorescent compound is obtained. The fluorescent compound is composited with other phosphatidyl choline such as DPPC (dipalmitoyl phosphatidylcholine), DSPC (disaturated phosphatidylcholine) and DAPC (1,2-dilauroyl-sn-glycero-3-phosphocholine) and DSPE-PEG2000 (distearoyl-phosphatidylethanolamine-polyethylene glycol 2000) to form a temperature-sensitive fluorescent nanomaterial. The fluorescent nanomaterial comprises the raw materials in percentage by mass as follows: 5%-30% of a fluorescent compound I, 60%-90% of the phosphatidyl choline and 1%-10% of DSPE-PEG2000. Nanoparticles are ultrasonically formed with a filming-rehydration method, the average particle size is about 50 nm, and the obtained temperature-sensitive fluorescent nanomaterial has good temperature response performance and has potential application value in the field of drug release.

Description

technical field [0001] The invention relates to the field of preparation of nanometer materials, in particular to a fluorescent compound based on tetraphenylethylene and its preparation method and application. Background technique [0002] Most of the traditional fluorescent compounds have high fluorescence quantum yield in dilute solution, but the fluorescence is weakened or even quenched in high concentration or aggregation state. This aggregation-induced quenching effect greatly limits their application range. Aggregation-induced luminescence was reported by Academician Tang Benzhong in 2001, which aroused widespread concern in the scientific community. Compounds such as pentaphenylsilacyclopentadiene, tetraphenylethylene, salicylazine, and triarylamine have all been found to have good aggregation-inducing effects. [0003] Tetraphenylethylene compounds are a typical type of aggregation-induced luminescent compounds. In the aggregation or solid state, the free rotation o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07C69/712C07C67/08B82Y40/00
CPCB82Y40/00C07C67/08C09K11/06C09K2211/1007C09K2211/1014C07C69/712
Inventor 赵云辉周智华刘立华谢文林唐子龙
Owner 深圳尚诺生物科技有限公司
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