Fluorine-boron dye molecule with donor and acceptor, and quaternary ammonium salt and preparation method thereof

A technology of donating acceptors and quaternary ammonium salts, which is applied in the field of fluoroboron dye molecules and their quaternary ammonium salts and preparations, which can solve the problems of limiting photothermal properties and short emission wavelengths, and improve water solubility and photothermal conversion Efficiency, long absorption wavelength, and good photothermal properties

Active Publication Date: 2021-03-16
HUNAN AEROSPACE MAGNET & MAGNETO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the absorption and emission wavelengths of conventional fluoroboron-dipyrrole fluorescent dye molecules are relatively short, usually around 500nm, which limits the application of their photothermal properties.

Method used

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  • Fluorine-boron dye molecule with donor and acceptor, and quaternary ammonium salt and preparation method thereof
  • Fluorine-boron dye molecule with donor and acceptor, and quaternary ammonium salt and preparation method thereof
  • Fluorine-boron dye molecule with donor and acceptor, and quaternary ammonium salt and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] The room temperature in this example refers to 25°C.

[0054]The preparation method of the donor acceptor fluorine boron dye molecule of formula (I) structure:

[0055] (1) Weigh 1.50g of 4-bromobenzaldehyde and 1.20g of pyridine-4-boronic acid and dissolve them in 20mL of 1,4-dioxane. 4.04 g of potassium carbonate was dissolved in 10 mL of pure water and added to the reaction system. The oxygen in the system was exhausted, and then 0.47 g of tetrakis(triphenylphosphine) palladium was added, and under the protection of nitrogen, the mixture was heated to reflux at 110° C. for 24 h. After the reaction, the 1,4-dioxane solvent was removed by a rotary evaporator, and then purified by a silica gel column to obtain 1.07 g of pyridine-4-carbaldehyde compound.

[0056] (2) Weigh 1.00g of pyridine-4-carbaldehyde compound and 0.88g of 2-methylpyrrole and dissolve in 120mL of dry dichloromethane, add 2 drops of trifluoroacetic acid, and react at room temperature for 12h under t...

Embodiment 2

[0061] The room temperature in this example refers to 22°C.

[0062] The preparation method of the donor acceptor fluorine boron dye molecule of formula (I) structure:

[0063] (1) Weigh 2.00g of 4-bromobenzaldehyde and 2.00g of pyridine-4-boronic acid and dissolve them in 25mL of 1,4-dioxane. 6.00 g of potassium carbonate was dissolved in 12 mL of pure water and added to the reaction system. The oxygen in the system was exhausted, and then 0.60 g of tetrakis(triphenylphosphine)palladium was added, and under the protection of nitrogen, the mixture was heated to reflux at 110° C. for 28 h. After the reaction, the 1,4-dioxane solvent was removed by a rotary evaporator, and then purified by a silica gel column to obtain 1.47 g of pyridine-4-carbaldehyde compound.

[0064] (2) Weigh 1.20g of pyridine-4-carbaldehyde compound and 1.05g of 2,4-dimethylpyrrole and dissolve it in 150mL of dry dichloromethane, add a drop of trifluoroacetic acid, and react at room temperature for 12h u...

Embodiment 3

[0069] The preparation method of the donor-acceptor fluoroboron dye molecule of formula (II) structure:

[0070] Weigh 0.04g of the fluoroboron dye molecule obtained in Example 1 and dissolve it in 10mL of toluene, add 0.35mL of methyl iodide (about 0.798g) under the condition of avoiding light, and heat the reaction at 60°C under the protection of nitrogen After 24 hours, no raw materials were spotted on the plate, and the solvent was spin-dried to obtain 43 mg of quaternary ammonium salt with fluoroboron dye molecules for acceptors, denoted as: BDP.

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Abstract

The invention discloses a fluorine-boron dye molecule with a donor and an acceptor and quaternary ammonium salt and a preparation method thereof, and a preparation method of the fluorine-boron dye molecule with the donor and the acceptor. The preparation method comprises the following steps: taking 4-bromobenzaldehyde, pyridine-4-boric acid and potassium carbonate as main reactants to obtain a pyridine-4-formaldehyde compound; taking a pyridine-4-formaldehyde compound, 2-methylpyrrole, an oxidant and boron trifluoride diethyl ether as main reactants to obtain a boron dipyrromethene compound containing a pyridine structure; taking a boron dipyrromethene compound containing a pyridine structure, 4-diphenylaminobenzaldehyde and acid as main reactants to obtain boron dipyrromethene dye molecules with donors and receptors. The invention also includes quaternary ammonium salts of boron fluoride dye molecules having donors and receptors and preparation method thereof. Compared with the conventional BODIPY dyes, the BODIPY containing pyridine and triphenylamine and the quaternary ammonium salt compound thereof have the advantages of long absorption wavelength, favorable photothermal properties and favorable chemical stability, and are suitable for photothermodynamic therapy.

Description

technical field [0001] The invention relates to a dye molecule and its quaternary ammonium salt and a preparation method, in particular to a fluoroboron dye molecule and its quaternary ammonium salt and a preparation method. Background technique [0002] In recent years, the incidence of cancer in the population has been increasing year by year, and the lethality of malignant tumors has seriously threatened people's lives. There are about 14 million cancer patients in the world every year, and nearly 8 million people die from cancer-related diseases. Traditional cancer treatments include surgical treatment, chemotherapy and radiotherapy and surgery, and patients may experience serious side effects and poor treatment outcomes. In recent years, with the development of science and technology, some emerging therapies for cancer treatment have emerged, including immunotherapy, gene therapy, photodynamic therapy (PDT), and photothermal therapy (PTT), etc. cancer treatment. [0...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/00C07F5/02
CPCC09B57/00C07F5/022
Inventor 李航朱沛宁胡盛青郑自儒
Owner HUNAN AEROSPACE MAGNET & MAGNETO
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