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Gallocyanine fluorescent probe based on aggregation-induced luminescent effect as well as preparation method and application thereof

A technology of aggregation-induced luminescence and fluorescent probes, applied in the field of organic compound preparation, can solve problems such as quenching of organic fluorescent compounds, and achieve great application potential, excellent luminescence performance, and easy functionalization.

Inactive Publication Date: 2016-12-07
XIDIAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to provide a cyanine fluorescent probe based on the aggregation-induced luminescence effect and its preparation method and application, aiming to solve the problem of aggregation-induced fluorescence quenching in organic fluorescent compounds

Method used

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  • Gallocyanine fluorescent probe based on aggregation-induced luminescent effect as well as preparation method and application thereof
  • Gallocyanine fluorescent probe based on aggregation-induced luminescent effect as well as preparation method and application thereof
  • Gallocyanine fluorescent probe based on aggregation-induced luminescent effect as well as preparation method and application thereof

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preparation example Construction

[0056] Such as figure 1 As shown, the preparation method of the cyanine fluorescent probe based on the aggregation-induced luminescent effect of the embodiment of the present invention includes the following steps:

[0057] S101: Reaction of TPE-CHO with quinoline salt or thiazole salt, the molar ratio of feed is 1:1.5~1.9, the reaction solvent is N,N-dimethylformamide DMF, the reaction temperature is room temperature, and the reaction time is 20min~3h;

[0058] S102: The obtained product is precipitated with diethyl ether and then washed with ethyl acetate or separated by column chromatography. The developing system is methanol:ethyl acetate=1:2.5. Collect the blue segment and spin dry it with a rotary evaporator.

[0059] The preparation method of the cyanine fluorescent probe based on the aggregation-induced luminescent effect of the embodiment of the present invention comprises the following steps:

[0060] Step 1: Reaction of TPE-CHO and quinoline salt, the feeding molar...

Embodiment 1

[0071] 1. The reaction of TPE-CHO and quinoline salt to prepare TPE-VQ:

[0072] Weigh 15mg of TPE-CHO and 23.7mg of quinoline salt, dissolve them in 1ml of N,N-dimethylformamide DMF, stir at room temperature for 20-40min under the catalytic condition of 10ul of triethylamine, the solution turns dark green.

[0073] 2. Separation and purification of TPE-VQ:

[0074] After the obtained product was precipitated with ether, it was separated by column chromatography. The developing system was methanol:ethyl acetate=1:2.5. The blue segment was collected and spin-dried with a rotary evaporator.

[0075] The reaction equation for the preparation experiment is:

[0076]

Embodiment 2

[0078] 1. The reaction of TPE-CHO and thiazole salt to prepare TPE-VS:

[0079] Weigh 10mg of TPE-CHO and 12.1mg of thiazole salt and dissolve it in 1ml of N,N-dimethylformamide DMF. Under the catalytic condition of 10ul triethylamine, stir at room temperature for 2-3 hours, the solution gradually changes from light yellow to deep pink .

[0080] 2. Separation and purification of TPE-VS:

[0081] Take a little of the obtained product, add a small amount of ether and centrifuge, take the supernatant and use ether to precipitate the solid, discard the supernatant. Ethyl acetate was added to the obtained solid and shaken, a small amount of solid dissolved, and the supernatant was discarded.

[0082] The reaction equation for the preparation experiment is:

[0083]

[0084] The application effect of the present invention is described in detail below in conjunction with the mensuration of compound TPE-VQ and TPE-VS:

[0085] 1. Determination of spectral characteristics of TP...

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Abstract

The invention discloses a gallocyanine fluorescent probe based on an aggregation-induced luminescent effect as well as a preparation method and an application thereof. The general formula of the gallocyanine fluorescent probe based on the aggregation-induced luminescent effect is as shown in a formula I, the gallocyanine fluorescent probe is a molecular probe which structurally merges a tetraphenylethylene (TPE) construction unit and a gallocyanine construction unit, and a synthetic process is simple and quick relatively; and the gallocyanine fluorescent probe has great application potential in the field of molecule imaging. A synthesized TPE compound has the advantages of being favorable in luminescent properties, simple and convenient to synthesize, easy in functionalization and the like, has small toxicity to living cells, has living cell membrane permeability and can be used for fluorescent imaging of living cells. The AIE effect gallocyanine fluorescent molecule probe is relatively simple and quick in synthetic process, has great application potential in the field of molecule imaging, and solves the problem that an organic fluorescent compound can gather and induce quenching of fluorescence.

Description

technical field [0001] The invention belongs to the technical field of organic compound preparation, and in particular relates to a cyanine fluorescent probe based on aggregation-induced luminescent effect, a preparation method and an application. Background technique [0002] At present, the usual organic fluorescent compounds have strong fluorescence in dilute solutions, and the fluorescence intensity is proportional to the concentration of fluorescent substances within a certain concentration range, but for relatively concentrated solutions, due to the interaction of electronic vibrations between molecules In non-radiative energy conversion, the interaction between planar fluorescent chromophores becomes stronger, forming excimer associations that lead to fluorescence quenching, and the phenomenon of fluorescence weakening or disappearance occurs, making its luminous efficiency in solid state or aggregated state comparable to that of The low-concentration dilute solution ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/10C07D277/64C09K11/06G01N21/64
CPCC07D215/10C07D277/64C09K11/06C09K2211/1029C09K2211/1037G01N21/6486
Inventor 张象涵王忠良赵娜王博张瑞丽宁蓬勃
Owner XIDIAN UNIV
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