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Novel long-wavelength boron tripyrrole fluorescent dye and synthesizing method thereof

A technology of fluoroboron tripyrrole and fluorescent dyes, which is applied in the synthesis field of novel long-wavelength fluoroboron tripyrrole dyes and derivatives thereof, and can solve the problem of harsh reaction conditions, long synthesis route, economy, operability and commercialization. Difficulties and other problems, to achieve the effect of fast and efficient method and increase the conjugation range

Inactive Publication Date: 2015-06-03
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, its synthesis needs to be catalyzed by noble metals (such as palladium), the synthesis route is long, the reaction conditions are harsh, and the scope of application of the technology is narrow. There are great difficulties in terms of economy, operability and commercialization.

Method used

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  • Novel long-wavelength boron tripyrrole fluorescent dye and synthesizing method thereof
  • Novel long-wavelength boron tripyrrole fluorescent dye and synthesizing method thereof
  • Novel long-wavelength boron tripyrrole fluorescent dye and synthesizing method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051]

[0052] In a 100mL round-bottomed flask, add 10mL of dried anhydrous 1,2-dichloroethane under an oxygen atmosphere. After 30min in an ice-water bath, inject 2.5mL (35mmol) of redistilled pyrrole, and add 0.25mL (3.5mmol) of ethyl alcohol dropwise. Acyl chloride, and rapid magnetic stirring, after 12 hours of reaction at room temperature, gradually add 3mL of triethylamine dropwise, and quickly add 8mL of boron trifluoride ether, raise the temperature to 50°C and react for 24 hours to complete the reaction, then extract with dichloromethane, Wash with water, dry over anhydrous sodium sulfate, filter, and concentrate under reduced pressure to obtain a crude product, which is then separated by silica gel column chromatography (300-400 mesh silica gel powder, n-hexane / ethyl acetate=6 / 1, V / V) to obtain dark purple Solid powder dye 2a, 181.7mg, yield 19.3%. 1 H NMR (300MHz, CDCl 3 )δ10.50(s, 1H), 7.61(s, 1H), 7.32(d, J=3.0Hz, 1H), 7.17(s, 1H), 7.01(s, 2H), 6.90(d, J=3.0 ...

Embodiment 2

[0056]

[0057] In a 100mL round-bottomed flask, add 10mL of dry 1,2-dichloroethane under an oxygen atmosphere, bathe in ice water for 30min, inject 2.5mL (35mmol) redistilled pyrrole, add 0.40mL (3.5mmol) 4-chlorobutyryl chloride dropwise, and Rapid magnetic stirring, after 12 hours of reaction at room temperature, gradually add 3 mL of triethylamine dropwise, and quickly add 8 mL of boron trifluoride ether, raise the temperature to 50°C and react for 24 hours to complete the reaction, extract with dichloromethane, wash with water, and filter , dried over anhydrous sodium sulfate, concentrated under reduced pressure to obtain a crude product, and then separated by silica gel column chromatography (300-400 mesh silica gel powder, n-hexane / ethyl acetate=8 / 1, V / V) to obtain a dark purple solid powder dye 2b, 314.8 mg, yield 27.0%. 1 H NMR (300MHz, CDCl 3 )δ10.50(s, 1H), 7.60(s, 1H), 7.39(s, 1H), 7.19(s, 1H), 7.03(s, 2H), 6.94(d, J=3.0Hz, 1H), 6.48(s, 1H), 6.39(s, 1H), 3.62(...

Embodiment 3

[0060]

[0061] In a 100mL round-bottomed flask, add 10mL of dry 1,2-dichloroethane under an oxygen atmosphere, bathe in ice water for 30min, inject 2.5mL (35mmol) redistilled pyrrole, add 0.62mL (3.5mmol) methyl fatty acid chloride dropwise, and quickly Magnetic stirring, after 12 hours of reaction at room temperature, gradually add 3 mL of triethylamine dropwise, and quickly add 8 mL of boron trifluoride ether, raise the temperature to 50 ° C and react for 24 hours to complete the reaction, extract with dichloromethane, wash with water, filter, Dry over anhydrous sodium sulfate, concentrate under reduced pressure to obtain the crude product, and then separate by silica gel column chromatography (300-400 mesh silica gel powder, n-hexane / ethyl acetate=6 / 1, V / V) to obtain dark purple solid powder dye 2c , 272.8mg, yield 21.0%. 1 H NMR (300MHz, CDCl 3 )δ10.49(s, 1H), 7.60(s, 1H), 7.30(s, 1H), 7.17(s, 1H), 7.00(s, 2H), 6.90(s, 1H), 6.47(s, 1H ), 6.38(s, 1H), 3.67(s, 3H), 2.8...

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Abstract

The invention discloses a novel long-wavelength boron tripyrrole fluorescent dye and a synthesizing method thereof. The fluorescent dye has a structure represented as the general formula A. Compared to prior art, the invention provides a boron tripyrrole fluorescent dye in which pyrrolyl is introduced to the 3rd and 5th sites of a matrix structure, and alkyl, halogeno and other heteratoms are introduced to a 8th site for substituting hydrocarbonyl and aryl, such that a conjugation range of BODIPY is widened. Therefore, spectral qualities of the compound is optimized, wherein relatively large maximal absorption and emission wavelengths, relatively large stokes displacement value, relatively large molar extinction coefficient, relatively large fluorescence quantum yield, and relatively narrow half band width are provided. The fluorescent dye is an ideal optical functional material. The material contains a plurality of modification sites, such that a novel synthetic long-wavelength fluorescent dye can be further designed. The dye can be used in analysis and detection in broader fields such as analytical chemistry, life science and environmental science.

Description

Technical field: [0001] The invention relates to a synthesis method of a novel long-wavelength boron tripyrrole dye and its derivatives, and belongs to the field of organic chemical industry and functional fluorescent dyes. Background technique: [0002] Boron dipyrrole (BODIPY) dyes are a very important class of organic biological dyes, and their parent structures are shown in the figure. [0003] [0004] Its excellent physical and chemical properties: high fluorescence quantum yield and molar extinction coefficient; good photostability; not easily affected by solvent polarity and pH value; narrow emission band; maximum absorption and emission wavelength in the visible region It is easy to carry out chemical modification, etc., so that it has been widely used in the fields of solar cells, fluorescent probes, biomolecular markers, pharmacological analysis and pathological diagnosis, and has become a hot research topic in their respective fields. [0005] Scholars such a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B57/00C09K11/06G01N33/52
Inventor 焦莉娟张敏商永嘉郝二宏
Owner ANHUI NORMAL UNIV