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Di(4-benzoindole)sulfone derivative and preparation method and application thereof

A technology of indole derivatives and indole benzene, which is applied in chemical instruments and methods, instruments, analytical materials, etc., can solve the problems of life overlap and other problems, and achieve the effects of shortened attenuation life, simple synthesis, and convenient detection

Active Publication Date: 2018-08-07
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Di(4-benzoindole)sulfone derivative and preparation method and application thereof
  • Di(4-benzoindole)sulfone derivative and preparation method and application thereof
  • Di(4-benzoindole)sulfone derivative and preparation method and application thereof

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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) into 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 = 2.3Hz, 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 = 3.3Hz, 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 constant with increasing solvent polarity.

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Abstract

The invention belongs to the field of organic light-emitting materials, and particularly relates to a di(4-benzoindole)sulfone derivative and a preparation method and application thereof. The di(4-benzoindole)sulfone derivative refers to an intramolecular charge transfer compound formed by using an indole derivative as the electron donor and diphenyl sulfone as the electron acceptor. Since the compound has two excited states including a localized state and a charge transfer state, the compound achieves fluorescence-delayed fluorescence dual emission; along with the increasing of solvent polarity, fluorescence emission peak displacement and lifetime are constant basically, and delayed fluorescence has distinct red shift while decay lifetime is shortened. Therefore, the derivative can serveas a novel fluorescence polarity sensor which utilizes self-fluorescence emission peak as the internal standard and detects polarity change in environments and organisms according to the simultaneouschange of delayed fluorescence emission and lifetime, and can be used for solution polarity tests.

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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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
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