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Near infrared fluoro-boron dipyrrole fluorescent dyes and synthesis method thereof

A fluoroboron dipyrrole, fluorescent dye technology, applied in azo dyes, organic dyes, luminescent materials, etc., can solve the problems of harsh reaction conditions, limited types, low luminous efficiency, etc., to increase the conjugation range and optimize photochemistry. The effect of nature

Inactive Publication Date: 2012-10-03
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current synthesis method is complex (noble metal catalysis, expensive raw materials, harsh reaction conditions, low yield), limited types, and low luminous efficiency; it is difficult to become a commercial dye

Method used

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  • Near infrared fluoro-boron dipyrrole fluorescent dyes and synthesis method thereof
  • Near infrared fluoro-boron dipyrrole fluorescent dyes and synthesis method thereof
  • Near infrared fluoro-boron dipyrrole fluorescent dyes and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Synthesis of compound IIa:

[0059] method one:

[0060]

[0061] In a 50 ml round bottom flask, add 20 ml of CH under argon 2 Cl 2 , add pyrrole (0.69ml, 10mmol) and 5-chloro-2-aldehyde isoindole (90mg, 0.5mmol) respectively, and add POCl which has been dissolved in 1ml dichloromethane 3 (470μl, 5mmol), after reacting for 16h, transfer to ice bath and add 1.0ml triethylamine, stir at room temperature for 10min, add 1.2ml boron trifluoride diethyl ether in ice water bath, and seal the round bottom flask. Stir overnight at room temperature. After the reaction is over, extract, dry, and concentrate under reduced pressure to obtain the crude product, and then undergo column chromatography (the stationary phase is silica gel, and the eluent is a mixed system of petroleum ether and dichloromethane with a volume ratio of 2 / 1) The dye was isolated as a red solid powder in 35% yield (54 mg).

[0062] Method Two:

[0063]

[0064] In a 50 ml round bottom flask, add ...

Embodiment 2

[0067] Synthesis of Compound IIb:

[0068]

[0069] In a 50 ml round bottom flask, add 20 ml of CH under argon 2 Cl 2 , respectively added 2-methylpyrrole (0.42ml, 5mmol) and 5-chloro-2-aldehyde isoindole (90mg, 0.5mmol), and added POCl which had been dissolved in 1ml dichloromethane 3 (470μl, 5mmol), after reacting for 2h, transfer to ice bath and add 1.0ml triethylamine, after stirring at room temperature for 10min, add 1.2ml boron trifluoride diethyl ether in ice water bath, seal the round bottom flask. Stir at room temperature for 2 hours. After the reaction, extract, dry, and concentrate under reduced pressure to obtain the crude product, and then go through column chromatography (the stationary phase is silica gel, and the eluent is a mixed system of petroleum ether and dichloromethane with a volume ratio of 2 / 1) A dark purple solid powder dye was obtained with a 41% yield (69 mg). 1 H NMR (300MHz, CDCl 3 ): δ10.59(s, 1H), 8.12(d, J=7.8Hz, 1H), 7.78(d, J=7.5Hz, 1H...

Embodiment 3

[0071] Synthesis of compound IIc:

[0072] method one:

[0073]

[0074] In a 50 ml round bottom flask, add 20 ml of CH under argon 2 Cl 2 , respectively added 2,4-dimethylpyrrole (0.5ml, 5mol) and 5-chloro-2-aldehyde isoindole (90mg, 0.5mmol), and added POCl which had been dissolved in 1ml dichloromethane 3 (470μl, 5mmol), after reacting for 2h, transfer to ice bath and add 1.0ml triethylamine, after stirring at room temperature for 10min, add 1.2ml boron trifluoride diethyl ether in ice water bath, seal the round bottom flask. Stir at room temperature for 2 hours. After the reaction, extract, dry, and concentrate under reduced pressure to obtain the crude product, and then go through column chromatography (the stationary phase is silica gel, and the eluent is a mixed system of petroleum ether and dichloromethane with a volume ratio of 2 / 1) A dark purple solid powder dye was obtained in 43% yield (78 mg).

[0075] Method Two:

[0076]

[0077] In a 50 ml round bo...

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Abstract

The invention relates to near infrared fluoro-boron dipyrrole fluorescent dyes and a synthesis method of the fluorescent dyes. The dyes have the general formula shown in the specification. The fluorescent dyes are synthesized from aldehyde or imine compounds of halogenated pyrrole or isoindazole and pyrrole derivatives by a one-pot method. The emission wavelength of the fluorescent dyes is more than 600nm, and the emission spectra of the monostyryl-substituted dyes and derivatives thereof can be up to 714nm. The fluorescent dyes have excellent light, physical and chemical performances of higher fluorescent quantum yield (0.61-0.91) and better light stability and the like, and has excellent application prospects in fluorescence labeling, biological imaging and other bioanalysis fields.

Description

Technical field: [0001] The invention relates to a class of near-infrared fluoroboron dipyrrole fluorescent dyes and a synthesis method thereof, belonging to the technical fields of functional fluorescent dyes, organic chemicals and fine chemicals. Background technique: [0002] Near-infrared (600-1000nm) fluorescence detection, using low-energy excitation photons, reduces the interference caused by Raman scattering, biological scattered light and autofluorescence on the detection results, enhances light penetration, and improves detection sensitivity. Through near-infrared fluorescence imaging Technology allows us to probe deeper into the inner mysteries of living organisms. At present, it has been widely used in many fields of biological analysis, such as DNA hybridization test, immune detection, early diagnosis of tumor cells, and gene mutation detection. [0003] With the continuous development of fluorescence analysis technology in the field of biological detection, th...

Claims

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Application Information

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IPC IPC(8): C09B57/00C09K11/06
CPCC09B23/04C09B23/0008C09B57/10C09K11/06C09K2211/1055
Inventor 焦莉娟于长江郝二宏
Owner ANHUI NORMAL UNIV
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