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A kind of bis(4-indolephenyl)sulfone derivative and its preparation method and application

A technology of indole derivatives and derivatives, applied in chemical instruments and methods, fluorescence/phosphorescence, instruments, etc., can solve the problems of overlapping lifetimes, achieve convenient detection, solve the effects of single fluorescence emission, and simple synthesis

Active Publication Date: 2021-09-17
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the disadvantages of this sensor are that a corresponding calibration curve is required to test the absolute polarity of the solvent and, when used at the cellular level, the lifetimes of fluorescent molecules and intracellular autofluorescence overlap

Method used

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  • A kind of bis(4-indolephenyl)sulfone derivative and its preparation method and application
  • A kind of bis(4-indolephenyl)sulfone derivative and its preparation method and application
  • A kind of bis(4-indolephenyl)sulfone derivative and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] (1) Synthesis of compound 2

[0040]Add 5-nitroindole (4.86 g, 30 mmol), 4,4'-difluorodiphenylsulfone (3.56 g, 14 mmol) and potassium carbonate (19.35 g, 140 mmol) to a 100 mL round bottom flask , under the protection of nitrogen, inject 70 mL of N-methylpyrrolidone, react at 140 °C for 4 hours, cool down to room temperature, pour the reaction solution into 500 mL of ice water, filter with suction, wash the filter cake repeatedly with water and petroleum ether, to obtain Gray-green solid 2, 97% yield. 1H NMR (400 MHz, DMSO) δ (ppm): 8.69 (d, J =2.3 Hz, 1H), 8.33 – 8.23 ​​(m, 2H), 8.10 (dd, J = 9.2, 2.3 Hz, 1H), 8.03 ( d, J = 3.4 Hz, 1H), 8.01 – 7.93 (m, 2H), 7.83 (d, J = 9.2 Hz, 1H), 7.07 (d, J = 3.3 Hz, 1H).

[0041] (2) Synthesis of compound 1

[0042] Add bis[4-(5-nitroindole)phenyl]sulfone (10 mmol) and 300 mL ethanol to a 500 mL round bottom flask, followed by stannous chloride dihydrate (100 mmol), under nitrogen protection Reflux for 20 hours, cool to room te...

Embodiment 2

[0048] Compound I obtained above was dissolved in n-hexane, toluene, dichloromethane, tetrahydrofuran, and N,N-dimethylformamide respectively to prepare a 0.05 μmol / L solution. Add 2mL of the solution to a 1 cm×1 cm×4 cm stoppered cuvette, and test its fluorescence emission spectrum, λ ex = 300 nm, the result is as figure 2 shown. As the polarity of the solvent increased, the shift of the fluorescence emission peak remained unchanged, and its intensity gradually weakened, while the emission peak of the delayed fluorescence gradually red-shifted, and its intensity gradually increased.

Embodiment 3

[0050] Compound I obtained above was dissolved in n-hexane and toluene, respectively, to prepare a 0.05 μmol / L solution. Add 2mL of the solution to a stoppered cuvette of 1 cm×1 cm×4 cm, and test its fluorescence decay lifetime, λ ex = 300 nm, the result is as image 3 shown. The fluorescence lifetime remains unchanged with increasing solvent polarity.

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Abstract

The invention belongs to the field of organic light-emitting materials, and specifically relates to a bis(4-indolephenyl)sulfone derivative and a preparation method and application thereof. The bis(4-indolebenzene)sulfone derivative proposed by the present invention is an intramolecular charge-transfer compound formed with indole derivatives as electron donors and diphenylsulfone as an electron acceptor. Due to the existence of localized states and charge-transfer states In two excited states, the compound exhibits fluorescence-delayed fluorescence dual emission phenomenon. As the polarity of the solvent increases, the fluorescence emission peak shift and lifetime remain basically unchanged, and the delayed fluorescence shows a significant red shift, while the decay lifetime shortens. Therefore, it can be used as a new type of fluorescent polarity sensor that uses the autofluorescence emission peak as the internal standard to detect the polarity changes in the environment and in vivo by delaying the simultaneous changes of fluorescence emission and lifetime, and can be used for solution polarity detection.

Description

technical field [0001] The invention belongs to the technical field of luminescent materials, and specifically relates to a bis(4-indolephenyl)sulfone derivative, a preparation method and an application of the compound. Background technique [0002] Due to the advantages of high sensitivity, good selectivity, and easy operation, luminescent materials are widely used in biological analysis and imaging. Many luminescent molecules will be affected by the polarity of the external solution during work. In addition, in biological systems, the polarity of the environment is a very important factor that regulates the physical and chemical properties of molecules. Especially at the cellular level, the polarity of the environment not only plays a key role in the internal activities of a large number of protein molecules, but also To a certain extent, it reflects the permeability of the membrane (Z. Yang, et al. Chem. Soc. Rev., 2014, 43, 4563.). Therefore, it is of great significance...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/08C07D409/14C09K11/06G01N21/64
CPCC07D209/08C07D409/14C09K11/06C09K2211/1029C09K2211/1092G01N21/6428
Inventor 朱亮亮李旭萍
Owner FUDAN UNIV