Boron dipyrromethene derivative dye ligand and preparation method thereof

Abstract

The invention discloses a boron dipyrromethene (BODIPY) derivative dye ligand, which is a novel BODIPY derivative dye ligand obtained by taking 1, 3, 5, 7-tetramethyl boron dipyrromethene as a core skeleton and grafting carboxyl on the 2, 6-position and pyridyl on the 8-position of the 1, 3, 5, 7-tetramethyl boron dipyrromethene. The ligand has excellent photophysical characteristics, good water solubility, good metal coordination ability and good metal ion susceptibility. The invention also discloses a preparation method of the boron dipyrromethene derivative dye ligand. The method is simpleand easy to control, raw materials are easy to obtain, and the method has universal adaptability.

Description

technical field

[0001] The invention relates to the field of organic dye ligand compounds, in particular to a fluoroboron dipyrromethene derivative dye ligand and a preparation method thereof. Background technique

[0002] Fluoroboron dipyrromethene (BODIPY) is a bright organic fluorescent dye molecule, due to its strong visible light absorption and high molar extinction coefficient, sharp fluorescence emission and high fluorescence quantum yield, and the pH of the chemical environment, solvent Due to their unique photophysical and chemical properties such as polarity insensitivity and good physiological stability, they are widely used in various fields such as sensors, fluorescent probes, information storage, optoelectronic devices, solar cells, and biomarkers in life sciences. In order to meet the application requirements in different fields, different functionalized BODIPY derivative fluorescent dyes have emerged, such as introducing methyl functional groups at the 1,3,5,...

Examples

Embodiment 1

[0045] A preparation method of a fluoroborate dipyrromethene derivative dye ligand, comprising the following steps:

[0046] Step 1. First, under magnetic stirring, add 2,4-dimethyl-1H-pyrrole-3-methyl benzyl (800mg, 3.5mmol) and 4-pyridinecarbaldehyde ( 200 μL, 1.97 mmol) and dry dichloromethane (200 mL), then dropwise added 200 μL trifluoroacetic acid (1.08 mmol) under a helium atmosphere, and reacted at 25 ° C for 20 h in the dark to obtain a reaction solution A;

[0047] Step 2. Add 380mg of 2,3-dichloro-5,6-dicyano-p-benzoquinone (1.67mmol) dropwise to the reaction solution A obtained in step 1 under stirring for oxidation reaction, and stir the reaction at 25°C for 4h, Obtain reaction solution B;

[0048] Step 3. Slowly add 6 mL of N,N-diisopropylethylamine (36.3 mmol) to the reaction solution B obtained in Step 2, and then dropwise add 9 mL of boron trifluoride-diethyl ether solution in an ice bath (0°C) (71mmol) to react, continue to stir and react for 8h, after thin...

Embodiment 2

[0053] A preparation method of a fluoroborate dipyrromethene derivative dye ligand, comprising the following steps:

[0054] Step 1. First, under magnetic stirring, add 2,4-dimethyl-1H-pyrrole-3-methyl benzyl (798.7mg, 3.5mmol) and 4-pyridinecarbaldehyde prepared according to the reference to a 500mL three-necked flask in sequence. (220μL, 2.2mmol) and dry dichloromethane (100mL), then add 200μL trifluoroacetic acid (1.08mmol) dropwise under a helium atmosphere, and react at 30°C in the dark for 40h to obtain a reaction solution A;

[0055] Step 2. Add 382.2mg of 2,3-dichloro-5,6-dicyano-p-benzoquinone (1.68mmol) dropwise to the reaction solution A obtained in step 1 under stirring for oxidation reaction, and stir the reaction at 30°C for 40h , to obtain reaction solution B;

[0056] Step 3. Slowly add 6mL of N,N-diisopropylethylamine (36.3mmol) to the reaction solution B obtained in step 2, and then add 9mL of boron trifluoride-ether solution (71mmol) dropwise at 25°C. Reac...

technical field

[0001] The invention relates to the field of organic dye ligand compounds, in particular to a fluoroboron dipyrromethene derivative dye ligand and a preparation method thereof. Background technique

[0002] Fluoroboron dipyrromethene (BODIPY) is a bright organic fluorescent dye molecule, due to its strong visible light absorption and high molar extinction coefficient, sharp fluorescence emission and high fluorescence quantum yield, and the pH of the chemical environment, solvent Due to their unique photophysical and chemical properties such as polarity insensitivity and good physiological stability, they are widely used in various fields such as sensors, fluorescent probes, information storage, optoelectronic devices, solar cells, and biomarkers in life sciences. In order to meet the application requirements in different fields, different functionalized BODIPY derivative fluorescent dyes have emerged, such as introducing methyl functional groups at the 1,3,5,...

Examples

Embodiment 1

[0045] A preparation method of a fluoroborate dipyrromethene derivative dye ligand, comprising the following steps:

[0046] Step 1. First, under magnetic stirring, add 2,4-dimethyl-1H-pyrrole-3-methyl benzyl (800mg, 3.5mmol) and 4-pyridinecarbaldehyde ( 200 μL, 1.97 mmol) and dry dichloromethane (200 mL), then dropwise added 200 μL trifluoroacetic acid (1.08 mmol) under a helium atmosphere, and reacted at 25 ° C for 20 h in the dark to obtain a reaction solution A;

[0047] Step 2. Add 380mg of 2,3-dichloro-5,6-dicyano-p-benzoquinone (1.67mmol) dropwise to the reaction solution A obtained in step 1 under stirring for oxidation reaction, and stir the reaction at 25°C for 4h, Obtain reaction solution B;

[0048] Step 3. Slowly add 6 mL of N,N-diisopropylethylamine (36.3 mmol) to the reaction solution B obtained in Step 2, and then dropwise add 9 mL of boron trifluoride-diethyl ether solution in an ice bath (0°C) (71mmol) to react, continue to stir and react for 8h, after thin...

Embodiment 2

[0053] A preparation method of a fluoroborate dipyrromethene derivative dye ligand, comprising the following steps:

[0054] Step 1. First, under magnetic stirring, add 2,4-dimethyl-1H-pyrrole-3-methyl benzyl (798.7mg, 3.5mmol) and 4-pyridinecarbaldehyde prepared according to the reference to a 500mL three-necked flask in sequence. (220μL, 2.2mmol) and dry dichloromethane (100mL), then add 200μL trifluoroacetic acid (1.08mmol) dropwise under a helium atmosphere, and react at 30°C in the dark for 40h to obtain a reaction solution A;

[0055] Step 2. Add 382.2mg of 2,3-dichloro-5,6-dicyano-p-benzoquinone (1.68mmol) dropwise to the reaction solution A obtained in step 1 under stirring for oxidation reaction, and stir the reaction at 30°C for 40h , to obtain reaction solution B;

[0056] Step 3. Slowly add 6mL of N,N-diisopropylethylamine (36.3mmol) to the reaction solution B obtained in step 2, and then add 9mL of boron trifluoride-ether solution (71mmol) dropwise at 25°C. Reac...

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