Near-infrared fluorescent compound with AIE performance as well as preparation method and application thereof

A fluorescent compound and near-infrared technology, applied in chemical instruments and methods, organic chemistry, fluorescence/phosphorescence, etc., can solve the problems of real-time imaging of mitochondria, no washing and photostability, etc., and achieve great application value and prospects, good Biocompatibility, photodamage reduction effect

Inactive Publication Date: 2018-11-23
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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However, none of them can achieve all the properties of li

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  • Near-infrared fluorescent compound with AIE performance as well as preparation method and application thereof
  • Near-infrared fluorescent compound with AIE performance as well as preparation method and application thereof
  • Near-infrared fluorescent compound with AIE performance as well as preparation method and application thereof

Examples

Experimental program
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Example Embodiment

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

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

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

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

[0063] Compound A and indole salt are heated and refluxed in ethanol and / or methanol for 12-30h. After removing the ethanol and / or methanol, dissolve with tetrahydrofuran; add saturated hexafluorophosphate aqueous solution, stir at room temperature for 0.2-1h, remove the solvent , Purification to obtain the fluorescent compound. The normal temperature means 25±5°C.

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

Example Embodiment

[0095] Example 1

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

[0097] 1. TPP-CHO-1 Preparation

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

[0099] (2) At 0℃, add 270μL of POCl 3 Slowly add dropwise to 24mL of DMF, stir at room temperature for 1h, add 2.0mmol of ethyl 1-parabenzoate-2,5-diphenylpyrrole to the aforementioned dissolved POCl 3 In ...

Example Embodiment

[0118] Example 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 the reaction for 24h; after the reaction, cool to room temperature, remove the solvent, collect the solid, dissolve the solid in 5mL of THF, and then add 5mL of saturated KPF 6 After stirring for 30 minutes, 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] NMR spectrometer and mass spectrometer were used to characterize TPP-1. 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 = 7.3 Hz, 3H), 1.29 (t, J = 6.8 Hz, 3H).

[012...

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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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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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