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A kind of amphiphilic azafluoroboron dipyrrole fluorescent dye and its preparation method

A technology of heterofluoroboron dipyrrole and fluorescent dyes, applied in azo dyes, organic dyes, luminescent materials, etc., can solve the problem of short ultraviolet absorption wavelength, etc., and achieve the effect of sharp peak shape and high intensity

Active Publication Date: 2017-10-03
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The UV absorption wavelength of the azafluoroboridipyrrole dye in the report is relatively short, and there is no related report on the azafluoroboridipyrrole dye with self-assembly characteristics and near-infrared absorption

Method used

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  • A kind of amphiphilic azafluoroboron dipyrrole fluorescent dye and its preparation method
  • A kind of amphiphilic azafluoroboron dipyrrole fluorescent dye and its preparation method
  • A kind of amphiphilic azafluoroboron dipyrrole fluorescent dye and its preparation method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1 (C 30 h 38 o 3 )

[0037] 4'-(3-propynyloxy)-4-(dodecyloxy)-chalcone (C 30 h 38 o 3 ) synthesis: p-propynyloxyacetophenone 15mmol is dissolved in the mixed solution of ethanol 50ml containing potassium hydroxide 60mmol and water 15ml, stirred for 30min, and the ethanol solution containing p-dodecyloxyphenylacetaldehyde 15mmol is slowly added dropwise , reacted at room temperature for 12h, filtered to obtain a precipitate, and washed with water to neutral pH to obtain a white powdery solid. 1 H NMR: (400MHz, CDCl 3 ):8.05(d,J=8.8Hz,2H),7.80(d,J=15.6Hz,1H),7.60(d,J=8.5Hz,2H),7.44(d,J=15.6Hz,1H), 7.07(d,J=8.7Hz,2H),6.93(d,J=8.6Hz,2H),4.78(d,J=2.1Hz,2H),3.99(t,2H),2.56(s,1H)1.80 (m,2H),1.46-1.27(m,18H),0.90(t,3H); image 3 shown.

[0038]

Embodiment 2

[0039] Embodiment 2 (C 62 h 74 BF 2 N 3 o 4 )

[0040]1,7-(4-dodecyloxy)phenyl-3,5-(4-propynyloxy)phenylazafluoroborondipyrrole (C 62 h 74 BF 2 N 3 o 4 ) Synthesis of fluorescent dye: 12 mmol of 4'-(3-propynyloxy)-4-(dodecyloxy)-chalcone and 400 mmol of ammonium acetate were mixed, refluxed for 12 hours, 200 ml of water was added, and 200 ml of dichloromethane was extracted Three times, dried over anhydrous sodium sulfate, filtered, and the filtrate was rotary evaporated to remove the organic solvent.

[0041] Add 50 ml of dry dichloromethane to the obtained compound under nitrogen atmosphere, add 10 mmol of DIPEA, add 12 mmol of boron trifluoride ether solution after 30 min, and react at room temperature for 24 h. Sequentially add saturated ammonium chloride solution, sodium chloride solution, and water to extract separately, the obtained organic solvent is dried with anhydrous sodium sulfate, and the obtained filtrate is filtered and rotary evaporated to remove the...

Embodiment 3

[0043] Embodiment 3 (C 72 h 96 BF 2 N 9 o 8 )

[0044] 1,7-(4-dodecyloxy)phenyl-3,5-(4-propynyloxy)phenylazafluoroboron dipyrrole 0.1mmol, azide diethylene glycol methyl ether 0.23mmol , 0.4mmol of copper sulfate pentahydrate, 0.5mmol of L-ascorbic acid were successively added into a mixed solvent of 30ml of acetonitrile, 30ml of tetrahydrofuran and 2ml of water, and stirred at room temperature for 24h. The organic solvent was removed by rotary evaporation, dichloromethane was added to dissolve and washed three times with water, the obtained organic solvent was dried with anhydrous sodium sulfate, and the obtained filtrate was filtered to remove the organic solvent by rotary evaporation. The product was obtained by preparative column chromatography, and the volume ratio of the eluent was dichloromethane:methanol=20:1. 1 H NMR: (400MHz, CDCl 3 ):8.07(m,8H),7.85(s,2H),7.10(d,j=9.0Hz,4H),6.99(d,j=8.9Hz,4H),6.92(s,2H),4.59(t ,4H),4.06(t,4H),3.90(t,4H),3.60(m,4H),3.50(m,4H)...

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Abstract

The invention relates to an amphiphilic aza-BODIPY fluorescent dye and a preparation method thereof. The preparation method comprises the following steps: reacting p-propynyloxy acetophenone with dodecyloxy phenylacetaldehyde to obtain chalcone; performing nitromethane nitration to obtain 4'-propynyloxy-4-dodecyloxy-2-nitromethylene-chalcone; carrying out coupling under an ammonium acetate condition, reacting the coupling product with boron trifluoride-ether to obtain an aza-BODIPY structure; and introducing different hydrophilic groups into the opposite alkynes of benzene with substituted 3rd and 5th positions of the parent structure of aza-BODIPY through click reactions so as to obtain the amphiphilic molecule. The provided synthesis method has the advantages of few steps, simple conditions, and high yield. Prominent aggregation phenomenon of amphiphilic BODIPY dye in water can be observed, the UV absorption of the dye is near 800 nm, the UV absorption peak is sharp, and the strength is extremely high.

Description

technical field [0001] The invention relates to the technical field of dye preparation methods, in particular to a class of amphiphilic azafluoroboron-dipyrrole fluorescent dyes and a preparation method thereof. Background technique [0002] The synthesis of tetraaryl azafluoro boron dipyrrole compounds was first reported in 1943 [J.Chem.Soc., 1943, 590-596]. This type of fluorescent dye has unique physical and chemical properties, such as: higher fluorescence Quantum yield, narrow fluorescence spectrum at half maximum width and good stability. However, this structure has not received social attention for the next 50 years. Until 2002, Donal F.O'Shea et al [Chem. The ultraviolet absorption wavelength is longer, and the fluorescence half-peak width is narrower. Since then, azafluoroboron-dipyrrole fluorescent dyes have been widely studied. In 2008, Kevin Burgess group [Tetrahedron, 2008, 64, 3642-3654] studied the effect of introducing methoxy groups on different positions ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B57/00C07F5/02C09K11/06
CPCC07F5/02C09B57/00C09K11/06C09K2211/1007C09K2211/1029C09K2211/1059C09K2211/107
Inventor 陈志坚刘勇朱莉高锋
Owner TIANJIN UNIV
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