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Boron-dipyrrolemethene fluorescent dye and preparation method and application thereof

A dipyrromethene and fluorescent dye technology, which is applied in the direction of methine/polymethine dyes, luminescent materials, organic dyes, etc., to achieve the effects of good biocompatibility, simple synthesis, and easy-to-obtain products

Active Publication Date: 2016-04-20
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the reported work, although there are a few cases of polar probes based on intermolecular hydrogen bond regulation with this property, their fluorescence properties are related to the hydrogen bond donating ability of the solvent rather than solvent polarity.

Method used

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  • Boron-dipyrrolemethene fluorescent dye and preparation method and application thereof
  • Boron-dipyrrolemethene fluorescent dye and preparation method and application thereof
  • Boron-dipyrrolemethene fluorescent dye and preparation method and application thereof

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Experimental program
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Embodiment approach

[0060] Another specific embodiment, said R 2 is H, methyl or ethyl. R 2 H is most preferred.

[0061] Another specific embodiment, said R 4 and R 5 each independently selected from C 1-4 of alkyl. More preferably, the R 4 and R 5 Each is independently preferably a methyl group or an ethyl group.

[0062] In a further preferred embodiment, said X is iodine.

[0063] In another preferred mode of practice, said n is an integer selected from 1-3, especially preferably n is 2 or 3.

[0064] More specifically, the boron fluoride complexed dipyrromethene fluorescent dye of the present invention is selected from compounds with the following structures:

[0065]

[0066] The present invention further provides a method for preparing boron fluoride complexed dipyrromethene (BODIPY) fluorescent dyes in which n is 1 or 4-8, comprising the following steps: reacting halogenated acid chlorides with pyrrole derivatives to obtain BODIPY dye intermediates, Substitution of secondary...

Embodiment 1

[0096] Synthesis of Fluorescent Dye Compound BP-1

[0097]

[0098] ①Synthesis of intermediate 1

[0099] 2,4-Dimethylpyrrole (2.0 mL, 19 mmol) and chloroacetyl chloride (0.7 mL, 8.8 mmol) were dissolved in 20 mL of dehydrated dichloromethane. The reaction solution was stirred at 0 °C for 30 min, and then at 25 °C for 30 min. Under ice-cooling, triethylamine (3.7 mL, 26 mmol) was added dropwise, and stirred at 25°C for 10 min. Boron trifluoride diethyl ether (5.5 mL, 44 mmol) was added dropwise and stirred overnight at 25°C. The solvent was distilled off under reduced pressure, and intermediate 1 (656 mg, 25.2%) was obtained by column chromatography. 1 HNMR (400MHz, CDCl 3 ), δ: 6.09(s, 2H, pyrrole-H), 4.77(s, 2H, CH 2 ),2.53(s,12H,CH 3 ).

[0100] ②Synthesis of Intermediate 2

[0101] Compound 1 (90.0 mg, 0.3 mmol), dimethylamine (0.15 mL, 2M in THF, 0.3 mmol), potassium iodide (7.5 mg, 0.045 mmol) and potassium carbonate (63.0 mg, 0.45 mmol) were dissolved in 10 m...

Embodiment 2

[0105] Synthesis of fluorescent dye compound BP-2:

[0106]

[0107] ①Synthesis of Intermediate 4

[0108] Compound 3 (82.0 mg, 0.314 mmol) was dissolved in 3 mL of dehydrated dichloromethane, and dimethylamine (3.14 mL, 2M in THF, 6.28 mmol) was added. The reaction solution was refluxed and stirred for three days under the protection of nitrogen, diluted with dichloromethane, and then washed with saturated NH 4 The crude product was obtained by washing with aqueous Cl solution and brine. Purified by column chromatography to obtain intermediate 4 (60.0 mg, 60.1%). 1 HNMR (400MHz, CDCl 3 ), δ: 6.06(s, 2H, pyrrole-H), 3.20(t, J=8Hz, 2H, CH 2 ), 2.56(t, J=8Hz, 2H, CH 2 ),2.51(s,6H,CH 3 ),2.47(s,6H,CH 3 ),2.35(s,6H,CH 3 ); 13 CNMR (100MHz, CDCl 3 ), δ: 154.2, 140.4, 137.4, 131.7, 121.8, 60.6, 45.4, 27.1, 16.6, 14.5; TOF (C 17 h 25 BF 2 N 3 + ) Theoretical value: 320.2104, experimental value: 320.2115.

[0109] ②Synthesis of Compound BP-2

[0110] Intermediate 4...

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Abstract

The invention provides a boron-dipyrrolemethene fluorescent dye and a preparation method and application thereof. The boron-dipyrrolemethene fluorescent dye has the general structural formula I. The fluorescence property of the boron-dipyrrolemethene fluorescent dye has an obvious solvent effect. The fluorescence is strong in a polar solvent, and the fluorescence is weak in a non-polar solvent. The fluorescent intensity and the fluorescent quantum yield of the fluorescent dye have a good linear relation with solvent polarity. Selectivity is good, the fluorescent dye is not interfered with negative and positive ions, active oxygen, amino acid, nucleic acid, protein, viscosity and pH and can be used for living cell subcellular organelle positioning fluorescence staining, and the molecular formula of the fluorescent dye is as shown in the description.

Description

technical field [0001] The invention relates to a class of fluorescent dyes in the field of fine chemical industry, its preparation method and application, in particular to a class of boron fluoride complexed dipyrromethene fluorescent dyes, a preparation method and its application in live cell dyeing. Background technique [0002] As a functional dye, fluorescent probes have been widely used in various fields of science and technology, especially in life sciences, clinical medical diagnosis, immunoassay and detection, etc. Among many fluorescent dyes, boron fluoride complexed dipyrromethene (BODIPY) fluorescent dye has high molar extinction coefficient, high fluorescence quantum yield, stable spectral properties, good photothermal and chemical stability, small molecular weight and low cytotoxicity. Low advantages, as biomolecular fluorescent probes and imaging fluorescent reagents have been widely used. [0003] Polarity is considered to be a very important environmental p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06C09B23/12G01N21/64C12Q1/02
CPCC07F5/022C09B23/12C09K11/06C09K2211/1096G01N21/643G01N21/6486
Inventor 樊江莉朱浩彭孝军杜健军
Owner DALIAN UNIV OF TECH
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