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BODIPY fluorescent dye, and preparation method and application thereof

A technology of fluorobodipyrrole and fluorescent dyes, which is applied in the direction of luminescent materials, azo dyes, organic dyes, etc., can solve the problem of not being able to change the absorption and emission wavelengths, achieve excellent photophysical and chemical properties, be easy for industrial production, and require equipment low effect

Inactive Publication Date: 2017-03-08
杭州博派生物技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, usually modification at the meso site cannot change its absorption and emission wavelengths

Method used

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  • BODIPY fluorescent dye, and preparation method and application thereof
  • BODIPY fluorescent dye, and preparation method and application thereof
  • BODIPY fluorescent dye, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029]

[0030] In a (100mL) dry round bottom flask, add 2-nitrobenzaldehyde (2g, 13mmol), under the protection of nitrogen, add pyrrole (35mL, 494mmol), then slowly add trifluoroacetic acid (245μL, 1.3 mmol), keep the reaction for 1 hour after the dropwise addition is completed. Then directly carry out vacuum distillation to distill off pyrrole, and the obtained black oil is purified by silica gel column chromatography (80% dichloromethane / petroleum ether) to obtain 1.92 g of imine product.

[0031] Weigh the imine product (500mg, 1.87mmol) and dissolve it with 100mL of dry dichloromethane, add DDQ (425mg, 1.87mmol) in batches, after stirring for 1 hour, slowly add 2mL (14.42mmol) of dry triethylamine, and react After 10 minutes, 2.2 mL (17.44 mmol) of BF was added dropwise 3 ·OEt 2 , Stir the reaction at room temperature for about 1 h to complete the reaction. Add 15 mL of distilled water to quench the reaction, extract with dichloromethane, and use anhydrous Na 2 SO ...

Embodiment 2

[0038]

[0039]In a dry (100 mL) round-bottomed flask, 5-fluoro 2-nitrobenzaldehyde (2 g, 11.8 mmol) was added, under nitrogen, pyrrole (17 mL, 236 mmol) was added, and trifluoroacetic acid was slowly added dropwise (5 μL, 0.02 mmol), keep the reaction for 2 hours after the dropwise addition is completed. Then directly carry out vacuum distillation to distill off pyrrole, and the obtained black oil is purified by silica gel column chromatography (80% dichloromethane / petroleum ether) to obtain 2.2 g of dark green imine product.

[0040] Weigh the imine product (300mg, 1.1mmol) and dissolve it with 100mL of dry n-hexane, add DDQ (239mg, 1.1mmol) in batches, after stirring for 2 hours, slowly add dry triethylamine (458μL, 3.3mmol), and react After 10 minutes, add BF dropwise 3 ·OEt 2 (2.2mL, 17.44mmol), stirred at room temperature for about 2h to complete the reaction. Add 15 mL of distilled water to quench the reaction, extract with n-hexane, and use anhydrous Na for the o...

Embodiment 3

[0047]

[0048] In a (100 mL) dry round-bottom flask, add 4-chloro-2-nitrobenzaldehyde (1 g, 5.4 mmol), under nitrogen protection, add pyrrole (14.2 mL, 204.8 mmol), then slowly add three Fluoroacetic acid (143 μL, 0.54 mmol), keep the reaction for 3 hours after the dropwise addition is completed. Then directly carry out vacuum distillation to distill off the pyrrole to obtain a brownish-yellow oil which is purified by silica gel column chromatography (80% dichloromethane / petroleum ether) to obtain 1.66 g of a brownish-yellow solid imine product.

[0049] Weigh the imine product (600mg, 1.99mmol) and dissolve it with 100mL dry toluene, add DDQ (452mg, 1.99mmol) in batches, after stirring for 3 hours, slowly add dry triethylamine (2.5mL, 18.03mmol), react After 10 minutes, add BF dropwise 3 ·OEt 2 (1.30mL, 10mmol), stirred at room temperature for about 3h to complete the reaction. Add 2 mL of distilled water to quench the reaction, extract with toluene, and use anhydrous ...

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Abstract

The invention relates to development of a BODIPY fluorescent dye with a novel structure and excellent photochemical properties and provides a BODIPY fluorescent dye, and a preparation method and application thereof, belonging to the field of organic chemistry. The BODIPY fluorescent dye has high fluorescence quantum yield (0.99), good photostability and other excellent photochemical properties; and the preparation method is simple, uses easily available raw materials, has low requirements on equipment and is easy for industrial production.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a fluoroboron dipyrrole fluorescent dye and a preparation method and application thereof. Background technique [0002] The development of fluoroboron dipyrromethene (BODIPY) fluorescent dyes has attracted extensive attention of researchers. This kind of fluorescent dyes was synthesized and reported for the first time in 1968 by Treibs and Kreuzer et al. BODIPY has excellent physical and chemical properties, such as high fluorescence quantum yield and molar extinction coefficient; good photostability and chemical stability; absorption and emission wavelength can be adjusted; easy to carry out chemical modification, etc. After decades of development, BODIPY fluorescent dyes have been widely used in the fields of laser dyes, fluorescent labeling and dyeing materials in fluorescent imaging, and indicators in fluorescent sensors. Therefore, it is of great significance to develop BOD...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06C09B57/00G01N21/64
CPCC07F5/022C09B57/00C09K11/06C09K2211/1096G01N21/6428
Inventor 卢华吴延平沈珍
Owner 杭州博派生物技术有限公司
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