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A class of azafluoroboron dipyrrole near-infrared fluorescent dyes and preparation method thereof

A technology of fluorine boron dipyrrole and fluorescent dyes, which can be applied to azo dyes, organic dyes, and luminescent materials, and can solve the problems of low absorption and emission wavelengths, poor water solubility, and low photothermal conversion efficiency.

Inactive Publication Date: 2021-09-10
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to solve the problems of poor water solubility, too low absorption and emission wavelength, and low photothermal conversion efficiency existing in the existing azafluoroboropipyrrole dyes, so that it cannot be applied on a large scale in the field of biomedicine. Azafluoroboron dipyrrole-like near-infrared dye, which has good water solubility, absorbs and emits in the near-infrared band, and has photothermal effects

Method used

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  • A class of azafluoroboron dipyrrole near-infrared fluorescent dyes and preparation method thereof
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  • A class of azafluoroboron dipyrrole near-infrared fluorescent dyes and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] (1), 4-(dodecyloxy)benzaldehyde raw material preparation

[0051] Raw material p-Hydroxybenzaldehyde (122.12mg, 1mmol), K 2 CO 3 K 2 CO 3 (690mg, 5mmol) was dissolved in 5-20ml of dimethylformamide, stirred at 25°C for 30-50 minutes, then bromododecane (594.8mg, 5mmol) was added to the mixed solution, and the temperature was kept at 25°C for reaction 12h-18h. Detection by thin layer chromatography (TLC). After the reaction was complete, it was extracted with dichloro, the organic phase was washed with water, dried with anhydrous MgSO4, finally filtered, rotary evaporated under reduced pressure, and purified by column chromatography. Drying in vacuo gave a yellow solid, compound 1; (yield about 79%).

[0052] p-Hydroxybenzaldehyde: K 2 CO 3 : The molar ratio of bromododecane is 1:5:5;

[0053] See attached figure 1

[0054] 1 H NMR (400MHz, CDCl 3 ):δ=7.91(d,J=8.0Hz,2H),6.90(d,J=,2H),4.20(d,J=,4H),2.53(s,J=,3H),2.28(t, J=,2H);

[0055] (2), the raw materi...

Embodiment 2

[0082] (1), 4-(dodecyloxy)benzaldehyde raw material preparation

[0083] Raw material p-Hydroxybenzaldehyde (122.12mg, 1mmol), K 2 CO 3 K 2 CO 3 (690mg, 5mmol) was dissolved in 5-20ml of dimethylformamide, stirred at 25°C for 30-50 minutes, then bromododecane (594.8mg, 5mmol) was added to the mixed solution, and the temperature was kept at 25°C for reaction 12h-18h. Detection by thin layer chromatography (TLC). After the reaction was complete, it was extracted with dichloro, the organic phase was washed with water, dried with anhydrous MgSO4, finally filtered, rotary evaporated under reduced pressure, and purified by column chromatography. Drying in vacuo gave a yellow solid, compound 1; (yield about 79%).

[0084] p-Hydroxybenzaldehyde: K 2 CO 3 : The molar ratio of bromododecane is (1:5:5:);

[0085] See attached figure 1

[0086] 1 H NMR (400MHz, CDCl 3 ):δ=7.91(d,J=8.0Hz,2H),6.90(d,J=,2H),4.20(d,J=,4H),2.53(s,J=,3H),2.28(t, J=,2H);

[0087] (2), the raw mat...

Embodiment 3

[0113] (1), 4-(dodecyloxy)benzaldehyde raw material preparation

[0114] Raw material p-Hydroxybenzaldehyde (122.12mg, 1mmol), K 2 CO 3 K 2 CO 3 (690mg, 5mmol) was dissolved in 5-20ml of dimethylformamide, stirred at 25°C for 30-50 minutes, then bromododecane (594.8mg, 5mmol) was added to the mixed solution, and the temperature was kept at 25°C for reaction 12h-18h. Detection by thin layer chromatography (TLC). After the reaction was complete, it was extracted with dichloro, the organic phase was washed with water, dried with anhydrous MgSO4, finally filtered, rotary evaporated under reduced pressure, and purified by column chromatography. Drying in vacuo gave a yellow solid, compound 1; (yield about 79%).

[0115] p-Hydroxybenzaldehyde: K 2 CO 3: Bromododecane molar ratio is (1:5:5:);

[0116] See attached figure 1

[0117] 1 H NMR (400MHz, CDCl 3 ):δ=7.91(d,J=8.0Hz,2H),6.90(d,J=,2H),4.20(d,J=,4H),2.53(s,J=,3H),2.28(t, J=,2H);

[0118] (2), the raw material pr...

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Abstract

The invention relates to a class of azafluoroboron dipyrrole near-infrared fluorescent dyes and a preparation method thereof. The dye is composed of hydrophilic chain, alkyl chain, electron donating group and azapyrrolidine skeleton. Obtain target dyestuff by following steps: (1) aromatic aldehyde and aromatic ketone react under alkaline condition, obtain chalcone; (2) obtain chalcone and nitromethane, react under alkaline condition; (3) Ring-closing reaction, with the intermediate product obtained in (2) and a large amount of ammonium acetate reaction; (4) coordination reaction, with the intermediate product obtained in (3) and -BF 2 A coordination reaction occurs; (5) an addition reaction; that is, (4) the obtained intermediate product undergoes a click addition reaction with the prepared oxygen chain to obtain the target dye. The target dye not only has good water solubility and good photothermal effect, but also can be used for single-wavelength excitation multimodal imaging, including photoacoustic imaging / fluorescence imaging, photothermal imaging, etc. guided by photodynamic and photothermal synergistic tumor therapy.

Description

technical field [0001] The invention relates to a class of azafluoroboron dipyrrole near-infrared fluorescent dyes and a preparation method thereof, belonging to the field of dyes and organic photothermal materials. Background technique [0002] In recent years, due to the development of optical imaging technology, microarray, electrophoresis and optical sensors, the design and synthesis of fluorescent dyes with strong absorption and fluorescence emission in the near-infrared region have attracted great interest of researchers. Especially in the field of biomedicine, due to the so-called window effect, in the near-infrared spectral range of 650-1000nm, the absorption of biological autofluorescence, tissue and cells will be reduced to the minimum, which means that the fluorescent dye will not penetrate biological tissues. Good permeability. The test object itself has less absorption of infrared light, so near-infrared dyes can greatly reduce background interference, and can ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B57/00C07F5/02C09K11/06
CPCC07F5/02C09B57/00C09K11/06
Inventor 陈志坚左家赫潘宏斐
Owner TIANJIN UNIV