Preparation method of near-infrared fluorescent molecule with aggregation-induced emission characteristic

Abstract

The invention discloses a preparation method of near-infrared fluorescent molecules with aggregation-induced emission characteristics. The molecular formula of the compound is shown in the specification. The invention discloses a preparation method and application of the solid-state near-infrared fluorescence emission molecule. The compound disclosed by the invention has the characteristic of aggregation-induced emission, the unique chemical structure of the compound enables the compound to emit near-infrared light, and the solid-state maximum fluorescence peak position is 770nm. Therefore, the molecule has a wide application prospect.

Description

technical field

[0001] The invention relates to the field of organic optical functional materials, namely the preparation method and photophysical properties of near-infrared fluorescent compounds. Background technique

[0002] At present, the study of near-infrared fluorescent molecules is a challenging work. At the same time, near-infrared (NIR, 700-900nm) fluorescent molecules have potential applications in biology and other fields. Therefore, the synthesis of materials with near-infrared luminescence is urgently needed.

[0003] In 2001, the team of academician Tang Benzhong proposed the concept of aggregation-induced emission (AIE), that is, molecules do not emit in solution, but have high fluorescence intensity in the aggregated state. Currently, the mechanism of AIE is widely considered to be intramolecular motion-limited and energy-dissipative-limited. In applications such as biomedicine, molecules are mostly used in aggregated states. Therefore, the aggregation ...

Examples

Embodiment 1

[0020] The synthetic method of above-mentioned compound 1, comprises the following steps:

[0021] Compound 1, the molecular formula is C 60 h 46 f 15 N 3 o 2 , the chemical formula of compound 1 is as shown in formula (I):

[0022]

[0023] Its preparation method, the steps are as follows:

[0024] 1) Compound 1 (0.5mmol, 0.381g) and 4-butoxydiphenylamine (2.5mmol, 0.603g), three (dibenzylideneacetone) palladium (0.038mmol, 0.022g), 2-dicyclohexyl Ketone-2',6'-diisopropoxy-1,1'-biphenyl (0.15mmol, 0.070g) and tripotassium phosphate (5.0mmol, 1.061g) were placed in a 25mL two-necked bottle under nitrogen protection , add 2 mL of toluene. 2) Add 0.5ml triethylamine and react at 110°C for 6h;

[0025] 2) React at 110°C for 24 hours. After the system was cooled, dichloromethane (50 mL) was added and extracted three times with water.

[0026] 3) The organic phase was dried overnight with anhydrous magnesium sulfate. The crude product was recrystallized with chlorofor...

Embodiment 2

[0029] The synthetic method comprises the following steps:

[0030] 1) Compound 1 (0.5mmol, 0.381g) and 4-butoxydiphenylamine (2.5mmol, 0.724g), three (dibenzylideneacetone) palladium (0.038mmol, 0.022g), 2-dicyclohexyl Ketone-2',6'-diisopropoxy-1,1'-biphenyl (0.15mmol, 0.070g) and tripotassium phosphate (5.0mmol, 1.061g) were placed in a 25mL two-necked bottle under nitrogen protection , add 2 mL of toluene. 2) Add 0.5ml triethylamine and react at 110°C for 6h;

[0031] 2) React at 110°C for 24 hours. After the system was cooled, dichloromethane (50 mL) was added and extracted three times with water.

[0032] 3) The organic phase was dried overnight with anhydrous magnesium sulfate. The crude product was recrystallized with chloroform / ethanol to obtain the compound (yield 45%)

[0033] The molar ratio of compound 1 to 4-butoxydiphenylamine is 0.5 mmol: 3.0 mmol.

[0034] Characterization 1. Solid-state fluorescence spectrum of fluorescent molecules:

[0035] The fluore...

technical field

[0001] The invention relates to the field of organic optical functional materials, namely the preparation method and photophysical properties of near-infrared fluorescent compounds. Background technique

[0002] At present, the study of near-infrared fluorescent molecules is a challenging work. At the same time, near-infrared (NIR, 700-900nm) fluorescent molecules have potential applications in biology and other fields. Therefore, the synthesis of materials with near-infrared luminescence is urgently needed.

[0003] In 2001, the team of academician Tang Benzhong proposed the concept of aggregation-induced emission (AIE), that is, molecules do not emit in solution, but have high fluorescence intensity in the aggregated state. Currently, the mechanism of AIE is widely considered to be intramolecular motion-limited and energy-dissipative-limited. In applications such as biomedicine, molecules are mostly used in aggregated states. Therefore, the aggregation ...

Examples

Embodiment 1

[0020] The synthetic method of above-mentioned compound 1, comprises the following steps:

[0021] Compound 1, the molecular formula is C 60 h 46 f 15 N 3 o 2 , the chemical formula of compound 1 is as shown in formula (I):

[0022]

[0023] Its preparation method, the steps are as follows:

[0024] 1) Compound 1 (0.5mmol, 0.381g) and 4-butoxydiphenylamine (2.5mmol, 0.603g), three (dibenzylideneacetone) palladium (0.038mmol, 0.022g), 2-dicyclohexyl Ketone-2',6'-diisopropoxy-1,1'-biphenyl (0.15mmol, 0.070g) and tripotassium phosphate (5.0mmol, 1.061g) were placed in a 25mL two-necked bottle under nitrogen protection , add 2 mL of toluene. 2) Add 0.5ml triethylamine and react at 110°C for 6h;

[0025] 2) React at 110°C for 24 hours. After the system was cooled, dichloromethane (50 mL) was added and extracted three times with water.

[0026] 3) The organic phase was dried overnight with anhydrous magnesium sulfate. The crude product was recrystallized with chlorofor...

Embodiment 2

[0029] The synthetic method comprises the following steps:

[0030] 1) Compound 1 (0.5mmol, 0.381g) and 4-butoxydiphenylamine (2.5mmol, 0.724g), three (dibenzylideneacetone) palladium (0.038mmol, 0.022g), 2-dicyclohexyl Ketone-2',6'-diisopropoxy-1,1'-biphenyl (0.15mmol, 0.070g) and tripotassium phosphate (5.0mmol, 1.061g) were placed in a 25mL two-necked bottle under nitrogen protection , add 2 mL of toluene. 2) Add 0.5ml triethylamine and react at 110°C for 6h;

[0031] 2) React at 110°C for 24 hours. After the system was cooled, dichloromethane (50 mL) was added and extracted three times with water.

[0032] 3) The organic phase was dried overnight with anhydrous magnesium sulfate. The crude product was recrystallized with chloroform / ethanol to obtain the compound (yield 45%)

[0033] The molar ratio of compound 1 to 4-butoxydiphenylamine is 0.5 mmol: 3.0 mmol.

[0034] Characterization 1. Solid-state fluorescence spectrum of fluorescent molecules:

[0035] The fluore...

Images