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Near-infrared aza-BODIPY dye and microwave synthesis method thereof

A fluorine boron dipyrrole and near-infrared technology, which is applied to azo dyes, organic dyes, chemical instruments and methods, and can solve problems such as low yield, long reaction time, and long completion time

Active Publication Date: 2017-03-08
WUHAN INST OF PHYSICS & MATHEMATICS CHINESE ACADEMY OF SCI
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

In the process of synthesizing tetraaryl azadipyrromethene compounds, the conventional heating method has the disadvantages of long reaction time (24h-72h) and low yield (12%-47%), which makes the whole synthetic route take a long time to complete , low yield

Method used

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  • Near-infrared aza-BODIPY dye and microwave synthesis method thereof
  • Near-infrared aza-BODIPY dye and microwave synthesis method thereof
  • Near-infrared aza-BODIPY dye and microwave synthesis method thereof

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Embodiment 1

[0040]Synthesis of near-infrared azafluoroboron dipyrrole dye compound 4:

[0041] 1. Synthesis of compound 1:

[0042] p-Hydroxyacetophenone (1.36g, 10mmol) and p-cyanobenzaldehyde (1.31g, 10mmol) were dissolved in 50mL of absolute ethanol, KOH (560mg, 30mmol) was added, stirred overnight at room temperature, and then KOH (560mg, 30mmol) was added , stirred at room temperature for 5h, suction filtered, the filtrate was adjusted to pH=4.0 with 3mol / L hydrochloric acid, precipitated, filtered with suction, and the filter cake was washed with 3mol / L hydrochloric acid to obtain compound 1 as light yellow solid powder (1.80g, yield 72.3%). 1 H NMR (500MHz, DMSO-d 6 )δ10.48(s,1H),8.10-8.05(m,5H),7.92(d,J=5.0Hz,2H),7.72-7.69(d,J=15.0Hz,1H),6.91-6.90(d ,J=5.0Hz,2H). 13 C NMR (126MHz, DMSO-d 6 )δ186.89,162.48,140.46,139.48,132.65,131.38,129.24,128.80,118.65,115.44,112.01.HRMS(ESI+)calcd forC 16 h 11 NO 2 [M+H] + 250.0863, found 250.0848.

[0043] 2. Synthesis of compound 2: ...

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Abstract

The invention belongs to the technical field of organic synthesis and particularly discloses near-infrared aza-BODIPY dye and a microwave synthesis method thereof. The compound structural formula of the aza-BODIPY fluorescent dye is shown in the abstract figure. The synthesis method comprises synthesis steps as follows: p-hydroxyacetophenone and p-cyanobenzaldehyde are taken as raw materials, and an alpha, beta-unsaturated ketone compound 1 containing conjugated double bonds is obtained; the compound 1 is subjected to heating reflux and Michael addition with nitromethane for nitrosation under the alkaline condition, and a compound 2 is obtained; the compound 2 reacts with ammonium acetate with a microwave method at the reaction temperature of 95 DEG C for 6 h, a tetraaryl-aza-dipyrromethene compound 3 is obtained; the compound 3 reacts with triethylamine and boron trifluoride to produce the near-infrared aza-BODIPY dye. The near-infrared aza-BODIPY dye and the synthesis method have the advantages that compared with a conventional heating method for synthesizing the fluorescent dye, the microwave method can greatly shorten the reaction time, reduce by-products and increase the reaction yield to a certain extent.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a near-infrared azafluoroboron dipyrrole fluorescent dye and a microwave synthesis method thereof. Background technique [0002] Near-infrared azafluoroboron dipyrrole dye, as a new type of fluorescent dye, has become a hot spot in the research of photofunctional materials in recent years because of its excellent optical properties and the characteristics of being a photosensitizer. Broad application prospects (J.Am.Chem.Soc.2004,126,10619-10631). Tetraaryl azadipyrromethene compounds and BF 2 Complexation prevents the isomerization of the bridge nitrogen bond connected to the pyrrole ring, and obtains a near-infrared azafluoroboron dipyrrole dye with a better rigid plane, showing excellent optical properties: the emission and absorption wavelengths of the fluorophore are in the near-infrared area; higher molar absorptivity (70000-80000M -1 cm -1 ) (Org.Lett.,2006,8...

Claims

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Application Information

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IPC IPC(8): C09B57/00C07F5/02C09K11/06
Inventor 周欣刘莲花陈世桢孙献平刘买利
Owner WUHAN INST OF PHYSICS & MATHEMATICS CHINESE ACADEMY OF SCI
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