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Multifunctional Organic Fluorescent Nanoparticles Based on Diketopyrrolopyrrole Compounds and Tetraphenylethylene Compounds and Their Preparation and Application

A technology of diketopyrrolopyrrole and fluorescent nanoparticles, which is applied in the fields of organic chemistry, fluorescence/phosphorescence, chemical instruments and methods, etc., can solve the problems of no visible fluorescence or weak fluorescence, difficult application, unguaranteed stability, etc. , to achieve the effect of being conducive to large-scale production and application, maintaining stability, and simple preparation method

Active Publication Date: 2019-07-19
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But so far, there are few reports on the preparation of organic multifunctional fluorescent nanoparticles by self-assembly, because the stability cannot be guaranteed, and it is easy to see no fluorescence or weak fluorescence after self-assembly, which is difficult for practical application.
There is no self-assembly of TPE and DPP by blending in the prior art to prepare multifunctional fluorescent nanoparticles that can be used for both sensing and imaging

Method used

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  • Multifunctional Organic Fluorescent Nanoparticles Based on Diketopyrrolopyrrole Compounds and Tetraphenylethylene Compounds and Their Preparation and Application
  • Multifunctional Organic Fluorescent Nanoparticles Based on Diketopyrrolopyrrole Compounds and Tetraphenylethylene Compounds and Their Preparation and Application
  • Multifunctional Organic Fluorescent Nanoparticles Based on Diketopyrrolopyrrole Compounds and Tetraphenylethylene Compounds and Their Preparation and Application

Examples

Experimental program
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Effect test

Embodiment 1

[0035] Preparation of multifunctional fluorescent nanoparticles. Such as figure 1As shown, in this example, two kinds of alkoxy-modified fluorescent molecules (ODPP and OTPE) were used as raw materials to prepare multifunctional fluorescent nanoparticles. In water, add two fluorescent compounds at a ratio of ODPP:OTPE of 1:4 to make the total concentration 50 μM / L. Self-assembly of amphiphiles ( figure 2 ), and the desired nanoparticles were prepared after ultrasonication for 0.5 hours. Such as image 3 As shown, the left picture is the hydrated particle size of nanoparticles measured by laser dynamic light scattering method, and the right picture is the fluorescence emission spectrum.

Embodiment 2

[0037] The fluorescence emission spectra of fluorescent nanoparticles in response to mercury ions are as follows: Figure 4 shown. In aqueous solution, the nanoparticles have emission peaks at 470nm and 540nm, corresponding to the fluorescence emission of TPE and DPP, respectively. With the addition of mercury ions, the fluorescence of TPE did not change much, while the fluorescence intensity of DPP gradually weakened. Use F 540 / F 470 to [Hg 2+ ] plotting to get Hg 2+ The limit of detection was 13 nM.

Embodiment 3

[0039] Application of fluorescent nanoparticles in dual-channel fluorescence imaging of cells. Add 21 μg / mL nanoparticle DPBS solution to the cultured dish with appropriate cell concentration and incubate for 0.5 hours. After washing away the nanoparticles in the culture dish with DPBS solution, the cells were imaged with a confocal fluorescence microscope. As shown in Figure 5, the nanoparticles can enter the HeLa cells well, and the fluorescence images obtained by both channels can clearly show the cytoplasm and nucleus.

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Abstract

The invention discloses a multifunctional organic fluorescent nanoparticle based on diketopyrrolopyrrole compounds and tetraphenyl ethylene compounds as well as preparation and application. The multifunctional organic fluorescent nanoparticle is formed by diketopyrrolopyrrole compounds and tetraphenyl ethylene compounds through molecular self-assembly. The multifunctional nanoparticle is high in stability, simultaneously has double-fluorescence emission and double-photon excitation induction fluorescence emission capabilities, is capable of achieving detection of ratio type Hg<2+> and dual-mode (double channels and double photons) cell imaging, and can be widely applied to the fields such as environmental engineering, biological imaging, biological medicines and the like.

Description

technical field [0001] The present invention relates to a self-assembled organic fluorescent nanoparticle, in particular to a kind that can be used for Hg 2+ The multifunctional fluorescent nanoparticle for detection and cell imaging and its preparation and application belong to the field of functional materials. Background technique [0002] Multifunctional nanoparticles have been extensively studied in the fields of chemical / biological sensing and bioimaging, drug loading (Lee, D.-E.; Koo, H.; Sun, I.-C.; Ryu, J.H.; Kim, K.; Kwon, I.C. Chemical Society Reviews 2012, 41, 2656-2672.). Among them, using the fluorescent signal of nanoparticles as the technical means of monitoring objects has the characteristics of simple operation, low cost and high reliability (Wolfbeis, O.S. Chemical Society Reviews 2015, 44, 4743-4768.). Composite fluorescent nanoparticles (such as core-shell nanoparticles) can achieve multifunctionalization of nanoparticles due to their different compone...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07D487/04G01N21/64
CPCC07D487/04C09K11/06C09K2211/1007C09K2211/1029C09K2211/1088G01N21/64
Inventor 刘正春聂凯旋石环环董波朝乐蒙
Owner CENT SOUTH UNIV
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