Novel rhodafluor fluorescent dye with characteristics of large stokes shift and near-infrared fluorescence emitting, and synthesis method thereof

A technology of Stokes and fluorescent dyes, which is applied in the field of new rhodin fluorescent dyes and their synthesis, can solve the problems of high fluorescence quantum yield, complex synthesis, and good photostability, and achieve cheap and easy-to-obtain raw materials and synthetic Simple steps and high reaction yield

Active Publication Date: 2015-06-17
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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Problems solved by technology

[0007] Few fluorescent dyes reported in the literature have the advantages of fluorescence emission wavelength in the near-infrared region, large Stokes shift, high fluorescence quantum yield, and good photostability.
Moreover, most fluorescent dyes are only obtained under laboratory conditions, the synthesis is complicated, the yield is low, and it is difficult to realize commercialization

Method used

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  • Novel rhodafluor fluorescent dye with characteristics of large stokes shift and near-infrared fluorescence emitting, and synthesis method thereof
  • Novel rhodafluor fluorescent dye with characteristics of large stokes shift and near-infrared fluorescence emitting, and synthesis method thereof
  • Novel rhodafluor fluorescent dye with characteristics of large stokes shift and near-infrared fluorescence emitting, and synthesis method thereof

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Experimental program
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Embodiment 1

[0058] Embodiment 1: the synthesis of rhodanine dye

[0059] 1. Synthesis of intermediate 4-methoxy-1,2-o-phenylenediamine

[0060]

[0061] 4-Methoxy-2-nitroaniline (16.8g, 0.1mol) was dissolved in 200mL of methanol, 1.68g of palladium carbon and 22mL of hydrazine hydrate were added, and reacted at 60°C for 6 hours to obtain the red oily intermediate 4-methoxy- 1,2-o-phenylenediamine.

[0062] 2. Synthesis of intermediate 6-methoxyquinoxaline

[0063]

[0064] Dissolve 4-methoxy-1,2-o-phenylenediamine in 350mL of acetonitrile, add dropwise 32mL of 40% aqueous solution of glyoxal, react at 60°C for 6 hours, evaporate the solvent, and collect the distilled water by vacuum distillation or column chromatography. Yellow needle intermediate 6-methoxyquinoxaline.

[0065] 3. Synthesis of intermediate 1,4-diethyl-6-methoxy-1,2,3,4-tetrahydroquinoxaline

[0066]

[0067] 6-Methoxyquinoxaline (5.5g, 0.034mol) was dissolved in 150mL of anhydrous toluene, sodium borohydride ...

Embodiment 2

[0075] Embodiment 2: Spectral properties of rhodanine dyes in different solvents

[0076] 1. Absorption spectra of rhodanine dyes in different solvents

[0077] Dissolve 10.7mg rhodanine dye in 5mL DMSO to make a concentration of 5mmol L -1 mother liquor. Pipette 8 μL of mother liquor into a sample bottle, and make 4 mL of solution with different solvents, the concentration is 10 μmol L -1 . Determination of the absorption spectra of rhodanine dyes in different solvents as attached Figure 4shown. It can be seen from the figure that the rhodan fluorescent dye has a large absorbance in polar solvents, and the molar extinction coefficient (ε) of the dye in the aqueous solution is 60097mol -1 ·L·cm -1 .

[0078] 2. Fluorescence emission spectra of rhodanine dyes in different solvents

[0079] Determination of 10μmol·L in different solvents -1 The fluorescence emission spectrum of rhodanfluorescein solution is attached Figure 5 shown. It can be seen from the figure tha...

Embodiment 3

[0080] Embodiment 3: Spectral properties of rhodanine dye in different pH aqueous solutions

[0081] 1. Absorption spectra of Rhodinium dye in different pH aqueous solutions

[0082] Pipette 8 μL to a concentration of 5mmol·L -1 The mother liquor into the sample bottle, made into aqueous solutions with different pH values, the concentration is 10μmol L -1 . Determination of the absorption spectrum of Rhodinium fluorescein dye in different pH solutions is as attached Image 6 shown. It can be seen from the figure that the configuration of Rhodinium fluorescein changes at pH=4~6, and the configuration is relatively stable in aqueous solution with pH≥6.

[0083] 2. Fluorescence emission spectra of Rhodinium fluorescein dyes in different pH aqueous solutions

[0084] Under the irradiation of 548nm excitation light, measure 10 μmol L in different pH solutions -1 The fluorescence emission spectrum of Rhodinium dye is attached Figure 7 shown. It can be seen from the figure t...

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Abstract

The invention relates to a novel rhodafluor fluorescent dye with characteristics of large stokes shift and near-infrared fluorescence emitting, and a synthesis method thereof, wherein catalytic hydrogenation reduction, glyoxal condensation, sodium borohydride reduction, Vilsmeier formulation, acid-catalyzed demethylation and other reactions are performed to obtain the intermediate, and the intermediate and diphenyl keto acid react to obtain the target product rhodafluor fluorescent dye. According to the present invention, compared with the conventional fluorescent dye, the obtained novel rhodafluor compound of the present invention has characteristics of high photostability, fluorescence emission wavelength in the near-infrared region (-660 nm), large stokes shift (-90 nm) and high fluorescence quantum yield (0.62), and can be used for the fields of light emitting materials/biological fluorescent probes, bioluminescence imaging and the like.

Description

technical field [0001] The invention belongs to the field of fluorescent dyes, and in particular relates to a novel rhodinyl fluorescent dye with large Stokes shift and near-infrared fluorescence emission and a synthesis method thereof. Background technique [0002] Xanthene-based fluorescent dyes have the characteristics of high molar extinction coefficient, high fluorescence quantum yield, and good photostability, and occupy an extremely important position in the field of organic dyes. As representative compounds of xanthene fluorescent dyes, rhodamine and fluorescein dyes are one of the most widely used and popular fluorophores in the field of biological and medical fluorescence imaging, and their synthesis, modification, structure and optical properties have been analyzed. There are many reports that some rhodamine or fluorescein (such as rhodamine B, rhodamine 6G, rhodamine 123, fluorescein, fluorescein isothiocyanate, etc.) products with excellent performance and suita...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/00C09K11/06
Inventor 徐兆超尹文婷刘晓刚
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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