Near-infrared fluorescent compound with AIE performance and its preparation method and application

A fluorescent compound, near-infrared technology, applied in chemical instruments and methods, organic chemistry, fluorescence/phosphorescence, etc., can solve the problems of inability to achieve real-time imaging of mitochondria, no washing and photostability, and achieve great application value and prospects, large Stokes shift, the effect of reducing light damage

Inactive Publication Date: 2019-11-05
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, none of them can achieve all the properties of live imaging of mitochondria, no washout, and photostability

Method used

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  • Near-infrared fluorescent compound with AIE performance and its preparation method and application
  • Near-infrared fluorescent compound with AIE performance and its preparation method and application
  • Near-infrared fluorescent compound with AIE performance and its preparation method and application

Examples

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preparation example Construction

[0059] In a preferred embodiment of the present invention, the preparation method includes the following steps:

[0060] Compound A and indole salt are refluxed and reacted in a solvent to obtain compound B, and an aqueous solution of hexafluorophosphate is added and stirred for reaction to obtain the fluorescent compound.

[0061] In a preferred embodiment of the present invention, the solvent includes one or both of ethanol and methanol.

[0062] In a preferred embodiment of the present invention, the preparation method includes the following steps:

[0063] Compound A reacts with indole salt in ethanol and / or methanol under reflux for 12-30h, removes ethanol and / or methanol, dissolves in tetrahydrofuran; adds saturated hexafluorophosphate aqueous solution, stirs at room temperature for 0.2-1h, removes solvent , and purify to obtain the fluorescent compound. The normal temperature refers to 25±5°C.

[0064] In a preferred embodiment of the present invention, the hexafluor...

Embodiment 1

[0096] This embodiment provides three preparation methods of compound A, the steps are as follows:

[0097] 1. TPP-CHO-1 preparation of

[0098] (1) Add 5.02mmol of 1,2-diphenylethyne, 20.08mmol of p-aminobenzoic acid ethyl ester and 0.5mmol of CuCl into a 100mL polymerization tube, vacuumize and fill with nitrogen three times, under nitrogen protection conditions, React at 120°C for 24 hours; after the reaction, dissolve with dichloromethane, wash three times with water, wash three times with 5% hydrochloric acid aqueous solution, dry with anhydrous magnesium sulfate, remove the solvent to obtain the crude product; pass the crude product through volume The eluent of methylene chloride and petroleum ether at a ratio of 1:2 is separated and purified to obtain 1-ethyl p-benzoate-2,5-diphenylpyrrole;

[0099] (2) At 0°C, 270 μL of POCl 3 Slowly add dropwise to 24mL of DMF, stir at room temperature for 1h, add 2.0mmol of 1-p-benzoic acid ethyl ester-2,5-diphenylpyrrole to the ...

Embodiment 2

[0119] This example provides TPP-1 The preparation method, the steps are as follows:

[0120] Take 0.6mmol of TPP-CHO-1 prepared in Example 1 and 0.65mmol of 1-ethyl-2,3,3-trimethyl-3H-indol-1-ium in 15mL of absolute ethanol Reflux for 24 hours; after the reaction, cool to room temperature, remove the solvent, collect the solid, dissolve the solid in 5 mL of THF, and then add 5 mL of saturated KPF 6 After stirring for 30 min, the solvent was removed and purified by silica gel column chromatography, the eluent was dichloromethane and methanol with a volume ratio of 10:1 to obtain TPP-1.

[0121] TPP-1 was characterized by nuclear magnetic resonance spectrometer and mass spectrometer, and the data are as follows:

[0122] 1 H NMR (400MHz, DMSO-d 6 )δ (ppm): 7.99-7.85 (m, 3H), 7.86-7.75 (m, 2H), 7.68 (s, 1H), 7.63-7.50 (m, 2H), 7.50-7.41 (m, 4H), 7.33 -7.26(m,7H),7.20(d,J=6.9Hz,2H),4.58(q,J=7.3Hz,2H),4.28(q,J=8.9,6.8Hz,2H),1.53(s, 6H), 1.42(t, J=7.3Hz, 3H), 1.29(t, J=6.8Hz...

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Abstract

The invention relates to the technical field of organic synthesis and novel materials and particularly relates to a near-infrared fluorescent compound with AIE performance as well as a preparation method and application thereof. According to the fluorescent compound, indole salts are used as receptors; a pyrrole donor and donors introduced with different conjugated structures in a site 2 and a site 5 of pyrrole are used for effectively regulating and controlling fluorescence emission of molecules; groups in a site 1, the site 2 and the site 5 are used for forming certain distortion with a pyrrole ring, so that the AIE performance is given to the compound; because of D-Pi-A actions in the molecules, the molecules can achieve long-wave-band light emission; the light emission wavelength is between 600 and 750nm and has greater Stokes shift. According to the fluorescent compound, the indole salts are used as targeting groups; the fluorescent compound is capable of achieving targeting imaging of mitochondria in various cells, has the advantages of washing-free property, low biotoxicity and high photobleaching resistance and the like in the imaging process, and is also capable of monitoring dyeing of the mitochondria in real time.

Description

technical field [0001] The invention relates to the technical field of organic synthesis and new materials, in particular to a near-infrared fluorescent compound with AIE performance and its preparation method and application. Background technique [0002] Fluorescent molecules have excellent properties in biological imaging, such as fast response, excellent time resolution, super sensitivity, in situ operability, simple operation, good reproducibility, etc. (Wang D, Su H, Kwok R T K, et al. Rational design of a water-soluble NIR AIEgen, and its applications for ultrafast wash-free cellular imaging and photodynamic cancer cell ablation [J]. Chemical Science, 2018, 9, 3685-3693.). At present, fluorescent probes with aggregation-induced luminescent properties have been widely used in the biological field. In the published prior art, there are some reports about AIE compounds and their applications in the biological field, such as the invention patent with the publication numb...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/06C09K11/06G01N21/64
CPCC07D403/06C09K11/06C09K2211/1007C09K2211/1029G01N21/6428G01N21/6486
Inventor 石建兵任飞刘派董宇平佟斌蔡政旭
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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