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A class of spectrally tunable aggregation-induced luminescence fluorescent materials and their preparation methods and applications

A technology of aggregation-induced luminescence and fluorescent materials, which is applied in the application field of labeling mitochondria, can solve the problems of fluorescence quenching and low solid quantum yield, and achieve good biocompatibility, high solid-state luminescence efficiency, and significant aggregation-induced luminescence The effect of the characteristic

Active Publication Date: 2019-08-20
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are many literature reports on mitochondrial biological imaging, and the research on biological imaging has also attracted the interest of scientific researchers. However, traditional fluorescent materials are prone to fluorescence quenching at high concentrations and have low solid quantum yields.

Method used

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  • A class of spectrally tunable aggregation-induced luminescence fluorescent materials and their preparation methods and applications
  • A class of spectrally tunable aggregation-induced luminescence fluorescent materials and their preparation methods and applications
  • A class of spectrally tunable aggregation-induced luminescence fluorescent materials and their preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] 1. Add 116.8mg (0.4mmol) 2,5-dibromobenzene-1,4-dicarbaldehyde, 1.0mL N,N-dimethylformamide, 0.5mL 2mol / L Na in a 10mL flask 2 CO 3 Aqueous solution and 190.04mg (1.0mmol) 4-trifluoromethylphenylboronic acid shown in formula I-1, stir and mix uniformly, then add 4.4mg (0.02mmol) palladium acetate, in nitrogen atmosphere, normal temperature reaction 10 hours, use Extracted with ethyl acetate, combined the organic phases, and dried with anhydrous sodium sulfate, filtered, concentrated under reduced pressure to remove the solvent, column chromatography (with a 20:1 volume ratio of petroleum ether and ethyl acetate as the eluent), 2,5-bis(4-trifluoromethylphenyl)benzene-1,4-dicarbaldehyde represented by formula II-1 was obtained.

[0047]

[0048]2. Mix 97mg (0.23mmol) 2,5-bis(4-trifluoromethylphenyl)benzene-1,4-dicarbaldehyde, 85mg (0.55mmol) 4-pyridineacetonitrile hydrochloride, 86μL (0.92mmol) Add triethylamine and 3mL ethanol to the flask, stir and react at 40°C fo...

Embodiment 2

[0054] Synthesis of aggregation-induced luminescent fluorescent materials with the following structural formula

[0055]

[0056] In this example, the 4-trifluoromethylphenylboronic acid in Example 1 was replaced with an equimolar amount of phenylboronic acid, and the other steps were the same as in Example 1 to obtain an aggregation-induced luminescent fluorescent material with a yield of 78%. The structural characterization data are: 1 H-NMR (400MHz, d 6 -DMSO) δ (ppm): 9.02 (d, J = 6.7Hz, 4H), 8.50 (s, 2H), 8.35-8.33 (m, 6H), 7.60-7.53 (m, 10H), 4.34 (s, 6H ); 13 C NMR (151MHz, d 6 -DMSO)δ(ppm): 151.20, 148.69, 146.47, 142.25, 138.13, 134.53, 131.65, 130.40, 129.80, 129.74, 124.38, 116.57, 111.64, 48.33; HRMS: m / z (M-2PF 6 ) 2+ The theoretical value is 258.1160, and the measured value is 258.1152.

Embodiment 3

[0058] Synthesize fluorescent materials with the following structural formula

[0059]

[0060] In this example, the 4-trifluoromethylbenzeneboronic acid in Example 1 was replaced with 4-methylbenzeneboronic acid in an equimolar amount, and the other steps were the same as in Example 1 to obtain a fluorescent material with a yield of 90%. The structural characterization data are: 1 H-NMR (400MHz, d 6 -DMSO)δ(ppm): 9.04(d, J=6.7Hz, 4H), 8.48(s, 2H), 8.35(d, J=6.9Hz, 4H), 8.30(s, 2H), 7.44(d, J=8.0Hz, 4H), 7.35(d, J=8.0Hz, 4H), 4.35(s, 6H), 2.39(s, 6H); 13 C NMR (151MHz, d 6 -DMSO)δ(ppm): 150.74, 147.99, 146.13, 141.18, 138.44, 134.82, 133.84, 130.90, 129.75, 129.54, 123.54, 116.03, 110.83, 47.55, 20.78; HRMS: m / z (M-2PF 6 ) 2+ The theoretical value is 272.1317, and the measured value is 272.1308.

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PUM

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Abstract

The invention discloses spectrum-adjustable gathering, inducing and light-emitting type fluorescent materials as well as a preparation method and an application thereof. The fluorescent materials have the structure formula shown in the description, wherein Ar denotes phenyl, C1-C4 halogenated alkyl substituted phenyl, C1-C4 alkyl substituted phenyl, C1-C4 alkoxy substituted phenyl, thienyl, C1-C4 alkyl substituted thienyl, furyl, C1-C4 alkyl substituted furyl or naphthyl, and the fluorescent materials with the gathering, inducing and light-emitting functions are obtained as follows: aldehyde derivatives and 4-pyridylacetonitrile hydrochloride as raw materials are subjected to a simple condensation reaction, an intermediate is obtained and reacts with methyl iodide to produce an ionic compound, and finally, the ionic compound is subjected to replacement through potassium hexafluorophosphate. The fluorescent materials have the gathering, inducing and light-emitting characteristics, are cation compounds, can specifically label mitochondria in live cells and are excellent mitochondrion imaging dye.

Description

technical field [0001] The invention belongs to the technical field of biomedical fluorescent materials, and in particular relates to a fluorescent material with aggregation-induced luminescent properties and adjustable spectrum, a preparation method of the fluorescent material and an application in marking mitochondria. Background technique [0002] Fluorescent materials have attracted great attention of scientists in recent years due to their great application value in optoelectronic devices, environmental sensors, biological sciences and other fields. Fluorescence detection not only has high sensitivity, but also overcomes a series of problems that require expensive and difficult-to-operate radioactive tracing reagents in biochemical experiments. Fluorescence imaging reveals the localization and measurement of molecules within cells, and sometimes enables detection at the single-molecule level. At present, there are many literature reports on mitochondrial bioimaging, an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/57C09K11/06C09B23/10C09B23/14G01N21/64
Inventor 赵娜李楠李朋飞刘艳艳
Owner SHAANXI NORMAL UNIV
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