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Infrared BODIPY fluorochrome as well as preparation method and application thereof

A fluorescent dye, infrared technology, used in luminescent materials, azo dyes, organic dyes, etc., can solve the problems of low molar absorption coefficient, low fluorescence quantum yield, weak fluorescence signal, etc., to achieve high molar absorption coefficient, enhanced organic Molecular fluorescence effect, the effect of narrow fluorescence emission spectrum

Inactive Publication Date: 2017-03-29
SUZHOU BAIYUAN GENT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The technical problem to be solved by the present invention is that the molar absorptivity of the existing BODIPY fluorescent dyes is low, the fluorescence quantum yield is small, the fluorescence signal is weak, and the problems of many synthesis steps

Method used

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  • Infrared BODIPY fluorochrome as well as preparation method and application thereof
  • Infrared BODIPY fluorochrome as well as preparation method and application thereof
  • Infrared BODIPY fluorochrome as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] The present embodiment provides the preparation method of BODIPY fluorescent dye (2):

[0038]

[0039] The preparation route is:

[0040]

[0041] The preparation method is:

[0042] S1. Take 0.25mL of chloroacetyl chloride and 0.70mL of 4-bromo-2-pyrrole carboxylic acid into a single-necked flask containing 1.5mL of dichloromethane solvent, stir at room temperature for 10min, and detect the raw material 4-bromo - The reaction of 2-pyrrole carboxylic acid is completed to obtain intermediate A1.

[0043] S2. Measure 8mL of boron trifluoride ether solution and 5mL of triethylamine and slowly add it dropwise to the reaction solution in step S1, and keep stirring. The reaction temperature is controlled at 25-30°C. Evaporate and remove the dichloromethane solvent to obtain a viscous liquid; use silica gel column separation and purification, the developer is petroleum ether (b.p.60-90°C): ethyl acetate (v:v) ratio of 5:1, to obtain intermediate B1.

[0044] S3. Get ...

Embodiment 2

[0052] The present embodiment provides the preparation method of BODIPY fluorescent dye (3):

[0053]

[0054] The preparation route is:

[0055]

[0056] The preparation method is:

[0057] Steps S1-S5 are the same as Steps S1-S5 of Example 1 to obtain intermediates A2, B2, C2 and D2 respectively.

[0058] S6. Under the protection of nitrogen, add 0.40mmol oxalyl chloride and THF solution for dissolving 0.48mmol intermediate D2 successively in a three-necked flask equipped with a reflux condenser, temperature sensor and stirrer, and stir; 150mL of methanol is added dropwise, and the reaction solution is React overnight at 70°C; take 100mL of triethylamine in the reaction solution, filter and evaporate to obtain the crude product (3); the crude product (3) is washed twice with saturated saline and passed through a silica gel column, and the developer is petroleum ether ( b.p.60-90°C): Ethyl acetate (v:v) ratio of 5:1; finally recrystallized with absolute ethanol to obt...

Embodiment 3

[0064] The present embodiment provides the preparation method of BODIPY fluorescent dye (4):

[0065]

[0066] The preparation route is:

[0067]

[0068] The preparation method is:

[0069] Steps S1-S2 are the same as Steps S1-S2 of Example 1 to obtain intermediates A3 and B3 respectively.

[0070] S3. Take 40mL of anhydrous tetrahydrofuran and add it to a 100mL single-necked flask, weigh 0.52mmol of intermediate B3, 0.35mmol of 4-aminobiphenyl, 0.12mmol of potassium iodide and 0.72mmol of anhydrous potassium carbonate and add it to the single-necked flask ;Under the protection of nitrogen, stir the reaction at room temperature for 5h; filter, and distill under reduced pressure to remove tetrahydrofuran; use silica gel column separation and purification, the developer is petroleum ether (b.p.60-90°C): ethyl acetate (v:v) is 5: 1, and added 3mL of triethylamine to obtain intermediate C3.

[0071] S4. On the 100mL three-necked flask, equipped with a stirrer, constant p...

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Abstract

The invention relates to the field of optical functional materials, and more specifically relates to an infrared BODIPY fluorochrome. The fluorochrome has a structure shown in a formula (1), wherein R1 and R2 are mutually independent and selected from C1-C10 alkyl, aromatic bases or heterocyclic aromatic bases; R3 is one of H atom, C1-C10 alkyl or aromatic bases. The fluorochrome has the advantages of narrow ultraviolet visible absorption spectroscopy and fluorescence emission spectrum, high molar absorption coefficient, high fluorescence quantum efficiency, good light stability, trace detection, and high sensitivity; and the fluorochrome can be applied to cell imaging, fluorescence probe, laser dye, fluorescence sensor and near infrared dynamics, and different application fields with good practicality.

Description

technical field [0001] The invention relates to the field of optical functional materials, in particular to an infrared BODIPY fluorescent dye and its preparation method and application. Background technique [0002] Fluorescent probes, as an important labeling method, have become an indispensable technical means in the detection of trace substances and biological science research, and have been widely used in biological imaging, disease diagnosis and phototherapy, and luminescent materials and other fields. The design and development of fluorescent probes based on dyes with high fluorescence quantum yield, large Stokes shift, long fluorescence emission wavelength and good biocompatibility are current research hotspots in this field. [0003] Near-infrared absorbing and fluorescently emitting dye molecules show great application prospects in many fields such as optical imaging, tumor diagnosis, infrared camouflage, nonlinear optical materials, and fluorescent labeling. In t...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06C09B57/00G01N21/64
CPCC07F5/022C09B57/00C09K11/06C09K2211/1007C09K2211/1029C09K2211/1055G01N21/6486
Inventor 车团结尤崇革谢小冬赵芳
Owner SUZHOU BAIYUAN GENT CO LTD
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