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Carbazolyl-based organic double-heterocyclic near-infrared fluorescent probe as well as preparation method and application thereof

A fluorescent probe and double heterocycle technology, applied in the field of near-infrared fluorescent probes, can solve the problems of small Stokes shift and short emission wavelength of fluorescent probes, and achieve large Stokes shift and relatively long emission wavelength. The effect of long, simple preparation method

Active Publication Date: 2020-11-20
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The fluorescent probe has defects with shorter emission wavelength and smaller Stokes shift

Method used

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  • Carbazolyl-based organic double-heterocyclic near-infrared fluorescent probe as well as preparation method and application thereof
  • Carbazolyl-based organic double-heterocyclic near-infrared fluorescent probe as well as preparation method and application thereof
  • Carbazolyl-based organic double-heterocyclic near-infrared fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] A method for preparing a carbazolyl-based organic biheterocyclic near-infrared fluorescent probe, the steps are as follows:

[0061] (1) Synthesis of 2,6-dimethyl-4-pyrylidene malononitrile 1

[0062] Put 2.48g (20mmol) of 2,6-dimethyl-4-pyrone and 1.59g (24mmol) of malononitrile in a 50ml single-necked flask, add 25ml of acetic anhydride, and heat the reaction at 142°C for 10 hours. The crude product was obtained by distillation under high pressure, and purified by silica gel chromatography column (solvent: mixed solvent of dichloromethane and methanol, methanol volume fraction 9-10%) to obtain the yellow-white solid product 2,6-dimethyl-4-pyranylidene Malononitrile, yield 86%.

[0063] The synthetic route is as follows:

[0064]

[0065] (2) Synthesis of 5-(9H-carbazol-9-yl)furan-2-carbaldehyde 2

[0066] in N 2 Under atmosphere, add 16mL N,N-dimethylformamide DMF, 2.006g (12mmol) carbazole and 2.65g (15mmol) 5-bromo-2-furfuraldehyde into a three-necked flask, ...

Embodiment 2

[0078] A method for preparing a carbazolyl-based organic biheterocyclic near-infrared fluorescent probe, the steps are as follows:

[0079] (1) The synthesis of 2,6-dimethyl-4-pyranylidene malononitrile 1 is the same as in Example 1;

[0080] (2) Synthesis of 5-(9H-carbazol-9-yl)thiophene-2-carbaldehyde 3

[0081] in N 2 Under the atmosphere, 16mL of DMF, 2.006g (12mmol) of carbazole and 2.87g (15mmol) of 5-bromothiophene-2-carbaldehyde were added into the three-necked flask, and stirred at room temperature for 30 minutes. Then add 0.38g (2mmol) cuprous iodide and 2.50g (18mmol) potassium carbonate, and react at 140°C for 48 hours. After the reaction, the solid was removed by filtration, and N,N-dimethylformamide was removed by a rotary evaporator. Purify by column chromatography (solvent: mixed solvent of n-hexane and ethyl acetate, ethyl acetate volume fraction 2-4%) to obtain pure product 5-(9H-carbazol-9-yl)thiophene-2-carbaldehyde, producing rate of 70%.

[0082] The...

experiment example

[0092] The near-infrared fluorescent probe II and near-infrared fluorescent probe III prepared above were subjected to liquid 1 H NMR and liquids 13 C NMR test, test results see respectively Figure 1-Figure 4 shown.

[0093]HITACHI F-7000 fluorescence spectrometer was used to test the fluorescence characteristics of the above-prepared near-infrared fluorescent probe II and near-infrared fluorescent probe III. The test results are shown in Figure 5-Figure 8 shown.

[0094] Test Results:

[0095] The excitation wavelength of the near-infrared fluorescent probe II is 465nm, the emission wavelength is 716nm, and the Stokes shift is 182nm. The excitation wavelength of the near-infrared fluorescent probe III is 455nm, the emission wavelength is 651nm, and the Stokes shift is 196nm; therefore, the near-infrared fluorescent probe of the present invention has a large Stokes shift and a long emission wavelength.

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Abstract

The invention relates to a carbazolyl-based organic double-heterocyclic near-infrared fluorescent probe, which has a structural formula I shown in the specification. The near-infrared fluorescent probe has strong emission in a near-infrared wavelength region, and has high photo-thermal property and chemical stability. The near-infrared fluorescent probe is simple in preparation method, high in fluorescence quantum yield and large in Stokes shift, and has important application prospects in development of near-infrared fluorescent probes and bioluminescence imaging, wherein X is O or S.

Description

technical field [0001] The invention relates to a carbazole-based organic biheterocyclic near-infrared fluorescent probe and a preparation method and application thereof, belonging to the technical field of near-infrared fluorescent probes. Background technique [0002] Bio-optical imaging is widely used in medical and biological research due to the advantages of mature detection instruments, high sensitivity, high contrast, high resolution, intuitive imaging, fast imaging speed and non-destructive testing. According to different detection methods, bio-optical imaging can be divided into fluorescence imaging, bioluminescence imaging, photoacoustic imaging, optical tomography, etc. Among them, fluorescent imaging (Fluorescent Imaging) uses fluorescent reporter groups (GFP, RFP and Cyt, etc. ) or fluorescent dyes is an important means of biomedical research, which can be used to study the location and concentration of target molecules, and can obtain higher resolution at the c...

Claims

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Application Information

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IPC IPC(8): C07D405/14C07D409/14C09K11/06G01N21/64
CPCC07D405/14C07D409/14C09K11/06G01N21/6428C09K2211/1029C09K2211/1088C09K2211/1092Y02E10/549
Inventor 刘鸿志王清正
Owner SHANDONG UNIV
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