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A kind of conjugated seven-membered fluoroboron dipyrrole fluorescent dye and its synthesis method

A technology of elemental fluoroboron dipyrrole and fluorescent dye, applied in the field of conjugated seven-membered fluoroboron dipyrrole fluorescent dye and its synthesis, can solve problems restricting the application of cell imaging, and achieve easy control of reaction conditions, mild reaction conditions, and universal The effect of applicability

Active Publication Date: 2022-03-18
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The maximum wavelength of ultraviolet absorption and fluorescence emission of traditional BODIPY dyes is generally between 470-530nm, which seriously restricts its application in cell imaging

Method used

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  • A kind of conjugated seven-membered fluoroboron dipyrrole fluorescent dye and its synthesis method
  • A kind of conjugated seven-membered fluoroboron dipyrrole fluorescent dye and its synthesis method
  • A kind of conjugated seven-membered fluoroboron dipyrrole fluorescent dye and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Weigh compound 1 seven-membered fluoroboron dipyrrole compound (248mg, 1mmol), take 30.00ml toluene, mix and dissolve, then add benzaldehyde (0.1ml, 1mmol), piperidine (0.09ml, 1mmol), acetic acid (0.06ml , 1 mmol), heated and stirred at 80°C for 2 hours to complete the reaction, the reactant was rotary evaporated, and purified by column chromatography to obtain a dark purple solid I-1 (111 mg), with a yield of 33.0%.

[0038]

Embodiment 2

[0040] Weigh compound 1 seven-membered fluoroboron dipyrrole compound (248mg, 1mmol), take 30.00ml toluene, mix and dissolve, then add benzaldehyde (0.2ml, 2mmol), piperidine (0.09ml, 1mmol), acetic acid (0.06ml , 1 mmol), heated and stirred at 80°C for 2 hours to complete the reaction, the reactant was rotary evaporated, and purified by column chromatography to obtain a dark purple solid I-1 (125 mg), with a yield of 37.2%. When the amount of benzaldehyde increased by 2 times relative to Example 1, the yield increased by 4.2%. X single crystal diffractogram and hydrogen spectrogram are the same as embodiment 1.

[0041]

Embodiment 3

[0043] Weigh compound 1 seven-membered fluoroboron dipyrrole compound (248mg, 1mmol), take 30.00ml toluene, mix and dissolve, then add benzaldehyde (0.2ml, 2mmol), piperidine (0.18ml, 2mmol), acetic acid (0.12ml , 2mmol), heated and stirred at 80°C for 2 hours to complete the reaction, the reactant was rotary evaporated, and purified by column chromatography to obtain a deep purple solid I-1 (126mg), with a yield of 37.5%. When the amounts of piperidine and acetic acid were increased by 2 times compared to Example 2, the yield had no significant change. X single crystal diffractogram and hydrogen spectrogram are the same as embodiment 1.

[0044]

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Abstract

The invention discloses a conjugated seven-membered fluoroboron dipyrrole fluorescent dye and a synthesis method thereof. The structure of the compound is as follows: wherein, the substituent R is selected from hydrogen, methoxyl group, dimethylamino group, ester group and fluorine any of the The dye is formed by one-step condensation of benzaldehyde and its para-substitute and the seven-membered fluoroboron dipyrrole compound under the catalysis of piperidine and acetic acid. The synthesis method is simple, the separation and purification are convenient, and the yield is high. The introduction of the aromatic ring substituent increases the conjugation of the molecule and red shifts the absorption and emission spectra, which should have good potential application prospects in the fields of biomarkers, cell imaging, or optoelectronic materials.

Description

technical field [0001] The invention discloses a conjugated seven-membered fluoroboron dipyrrole fluorescent dye and a synthesis method thereof, belonging to the field of fine chemical industry. The dye can be widely used in the fields of environment, analysis, material science and the like. Background technique [0002] Fluorine-boron fluorescent dyes (BODIPY) are a class of fluorescent compounds with excellent photophysical and chemical properties that have been developed in the past two decades and have been widely valued. Due to its good stability, modifiability, high molar extinction coefficient and good oxidation potential, at its modifiable position, the BODIPY dye can be adjusted by selectively inserting groups with corresponding functions. Optical properties such as absorption wavelength, stability and chemical properties, and physical properties such as solubility. At present, it is widely used in biological labeling, organelle fluorescence imaging, optoelectronic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06C09B57/00
CPCC09K11/06C07F5/022C09B57/00C09K2211/1029C09K2211/104
Inventor 张诺诺文柳晏佳莹刘德保郑开波
Owner CHINA THREE GORGES UNIV
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