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Novel AIE (Aggregation Induced Emission) red fluorescent dye

A red-light fluorescence and AIE technology, applied in the field of red-light fluorescent dyes, can solve problems such as no light emission and weak light emission that affect wide application, achieve strong penetrating power, simple synthesis route, and avoid cell self-absorption and autofluorescence interference effect

Inactive Publication Date: 2018-05-15
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although traditional fluorescent dyes such as rhodamine, fluorescein, BODIPY and some coumarin dyes have high fluorescence quantum efficiency in dilute solutions, due to the aggregation-caused quenching (ACQ) phenomenon, these dyes can be used at high concentrations and The luminescence is weak or non-luminous in the solid state, which affects its wide application in the above fields

Method used

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  • Novel AIE (Aggregation Induced Emission) red fluorescent dye
  • Novel AIE (Aggregation Induced Emission) red fluorescent dye
  • Novel AIE (Aggregation Induced Emission) red fluorescent dye

Examples

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Embodiment 1

[0020] Embodiment 1: the synthesis of dyestuff

[0021] Dissolve 272mg of compound 1 in 10mL of methanol, add 150mg of 40% glyoxal, react at room temperature for 12 hours, and observe that a yellow precipitate is formed in the system; filter the yellow precipitate, wash the precipitate three times with 50mL of ethanol, and obtain 213mg of a yellow powdery solid, namely It is the product dye 1 with a yield of 72.45%. HRMS(ESI) m / z: calcd for [M+1]+, 295.110; found, 295.119. 1 H NMR (400MHz, DMSO-d 6 )δ10.99(s,2H), 8.97(s,2H),8.54(s,2H),7.76(dd,J=7.7,1.5Hz,2H),7.57–7.24(m,2H),6.98(t ,J=7.8Hz, 4H). 13 C NMR (400MHz, CDCl 3 ) 168.01, 160.55, 159.99, 134.35, 133.23, 119.96, 117.46.

Embodiment 2

[0022] Embodiment 2: The present invention: cell imaging of fluorescent dyes

[0023] Dissolve the dye in DMSO solution to make 2.0 × 10 -5 mol / L solution, add 2 μL of the above solution into 2 mL of cell culture medium, and use this as a culture medium to culture HeLa cells at 37°C for 1 hour. Through a laser confocal scanning microscope, use 425nm as an excitation wavelength under the red light channel. It is observed that there is a strong signal in the liposome of the cell, indicating that the probe can be selectively aggregated in the liposome to generate fluorescence, which can be used for imaging and has high selectivity.

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Abstract

The invention discloses a novel AIE (Aggregation Induced Emission) red fluorescent dye, and the molecular structural formula of the novel AIE red fluorescent dye is as shown in the description. The fluorescent dye emits red fluorescence at the solid state and the aggregative state, and the emission peak is located at 617 nm. In addition, the fluorescent dye can be used in the lipidosome imaging ofa cell, and is relatively high in selectivity.

Description

technical field [0001] The invention relates to the field of fluorescent dyes, and relates to a red fluorescent dye based on aggregation-induced emission (AIE) and intramolecular excited state proton transfer (ESIPT) mechanisms. Background technique [0002] Organic small molecule fluorescent dyes are widely used in biological imaging, organic light-emitting diodes, dye-sensitized solar cells, photodynamic anti-tumor drugs and other fields. Although traditional fluorescent dyes such as rhodamine, fluorescein, BODIPY and some coumarin dyes have high fluorescence quantum efficiency in dilute solutions, due to the aggregation-caused quenching (ACQ) phenomenon, these dyes can be used at high concentrations and In the solid state, the luminescence is weak or non-luminous, which affects its wide application in the above fields. Aggregation-induced emission (AIE) phenomenon describes a class of fluorescent dyes that are opposite to the ACQ effect. Its fluorescence is weak or non-l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C09B26/02C07C249/16C07C251/88
Inventor 宋相志龚隽一苏远安廖立德杨雷张帆
Owner CENT SOUTH UNIV
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