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Triphenylamine-based organic near-infrared fluorescent probe as well as preparation method and application thereof

A fluorescent probe, triphenylamine-based technology, applied in the field of near-infrared fluorescent probes, can solve the problems of no triphenylamine-based near-infrared organic fluorescent probe report, small Stokes shift, short emission wavelength, etc. The effect of high rate, large Stokes shift and longer emission wavelength

Inactive Publication Date: 2021-01-29
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the fluorescent molecule has the defects of short emission wavelength and small Stokes shift.
[0005] After searching, there is no report about triphenylamine-based near-infrared organic fluorescent probes with large Stokes shift and large emission wavelength.

Method used

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  • Triphenylamine-based organic near-infrared fluorescent probe as well as preparation method and application thereof
  • Triphenylamine-based organic near-infrared fluorescent probe as well as preparation method and application thereof
  • Triphenylamine-based organic near-infrared fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] A preparation method based on a triphenylamine-based organic near-infrared fluorescent probe, the steps are as follows:

[0058] (1) Synthesis of hept-2,5-diyn-4-ol (1)

[0059] Under a nitrogen atmosphere, put 22.46ml of anhydrous tetrahydrofuran in a 100ml three-necked flask, cool down to -78°C, then add 10ml of n-butyllithium with a syringe, stir for 10 minutes, and then add 0.6005g (15mmol) of propyne in tetrahydrofuran The solution was added dropwise into the reaction flask, and after stirring for 10 minutes, 0.3001 g (5 mmol) of methyl formate was added dropwise into the reaction flask, and the mixture was kept at -78°C for 2 hours, and then the temperature was raised to -40°C. React for 1.5 hours. After the reaction was completed, water was added and the reaction temperature was slowly raised to room temperature. Extracted with diethyl ether (3x300ml), dried over anhydrous magnesium sulfate. The crude product was obtained by distillation under reduced pressure...

experiment example

[0083] The organic near-infrared fluorescent probe 2-(2,6-bis((E)-4-(diphenylamino) styryl)-((E)-4-(diphenylamino) styryl)- 4H-thiopyran-4-alkylene) malononitrile for liquid 1 H NMR and liquids 13 C NMR test, test results see respectively Figure 1-Figure 2 shown.

[0084] The organic near-infrared fluorescent probe 2-(2,6-bis((E)-4-(diphenylamino)styryl)-4H-thiopyran-4 prepared above was detected by HITACHI F-7000 fluorescence spectrometer. -Alkylene) malononitrile fluorescence properties are tested, the test results are shown in Figure 4 shown.

[0085] Test Results:

[0086] The excitation wavelength of the organic near-infrared fluorescent probe 2-(2,6-bis((E)-4-(diphenylamino)styryl)-4H-thiopyran-4-alkylene)malononitrile is 510nm, the emission wavelength is 720nm, and the Stokes shift is 210nm. Therefore, the near-infrared fluorescent probe of the present invention has a large Stokes shift and a longer emission wavelength.

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PUM

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Abstract

The invention relates to a triphenylamine-based organic near-infrared fluorescent probe, and the structural formula of the organic near-infrared fluorescent probe is shown as the following formula I.The near-infrared fluorescent probe provided by the invention has strong emission in a near-infrared wavelength region, and has high photo-thermal property and chemical stability. The near-infrared fluorescent probe provided by the invention is simple in preparation method, large in Stokes shift, relatively long in emission wavelength and good in chemical stability, and has important application prospects in development of near-infrared fluorescent probes and bioluminescence imaging.

Description

technical field [0001] The invention relates to a triphenylamine-based organic near-infrared fluorescent probe and a preparation method and application thereof, belonging to the technical field of near-infrared fluorescent probes. Background technique [0002] As a visual detection tool, the fluorescent probe method has the advantages of high sensitivity, good selectivity, easy operation, real-time monitoring, and no damage to biological samples, so it is widely used in many fields such as chemistry, biology, and medicine. . Near-infrared organic fluorescent materials have attracted extensive attention for their potential applications in organic electroluminescent semiconductors (OLEDs), crystal lasers (amplified spontaneous emission), solar cells, biological imaging, photothermal therapy, and detection and sensing. The near-infrared wavelength range is mainly located at 650-900nm. Compared with most traditional ultraviolet and visible light, near-infrared light has stronge...

Claims

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Application Information

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IPC IPC(8): C07D333/24C09K11/06G01N21/64
CPCC07D333/24C09K11/06C09K2211/1092G01N21/6486
Inventor 刘鸿志王清正杨慧中
Owner SHANDONG UNIV
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