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

A technology of aggregation-induced luminescence and fluorescent molecules, applied in the field of organic photofunctional materials

Pending Publication Date: 2022-04-12
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Currently, the study of near-infrared

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0019] Example 1

[0020] The synthesis method of the above compound 1 includes the following steps:

[0021] Compound 1, molecular formula C 60 Hide 46 Fly 15 N 3 O 2 , The compound 1 molecular chemical formula is as shown in the formula (I):

[0022]

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

[0024] 1) Compound 1 (0.5 mmol, 0.381 g) and 4-butoxy diphenine (2.5 mmol, 0.603 g), three (dibenzyl acetone) palladium (0.038 mmol, 0.022 g), 2-bicyclic Ketone-2 ', 6'-diisopropoxy-1,1'-biphenyl (0.15 mmol, 0.070 g) and tripotassium phosphate (5.0 mmol, 1.061g) are placed in 25 ml of two-neck, nitrogen protection 2 ml of toluene was added. 2) 0.5 ml of triethylamine was added and reacted at 110 ° C for 6 h;

[0025] 2) 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 over the night with anhydrous magnesium sulfate. The crude product was recrystallized by chl...

Example Embodiment

[0028] Example 2

[0029] The synthesis method includes the following steps:

[0030] 1) Compound 1 (0.5 mmol, 0.381 g) with 4-butoxy dipheniline (2.5 mmol, 0.724 g), three (dibenzylcetone) palladium (0.038 mmol, 0.022 g), 2-bicyclic Ketone-2 ', 6'-diisopropoxy-1,1'-biphenyl (0.15 mmol, 0.070 g) and tripotassium phosphate (5.0 mmol, 1.061g) are placed in 25 ml of two-neck, nitrogen protection 2 ml of toluene was added. 2) 0.5 ml of triethylamine was added and reacted at 110 ° C for 6 h;

[0031] 2) 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 over the night with anhydrous magnesium sulfate. The crude product was recrystallized by chloroform / ethanol to give a compound (45% yield)

[0033] The molar ratio of the compound 1 and 4-butoxybenafiline is 0.5 mmol: 3.0 mmol.

[0034] Characterization 1, solid state fluorescence spectrum of fluorescent molecules:

[0035] ...

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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 ...

Claims

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Application Information

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IPC IPC(8): C07C255/42C07C253/30C07C253/34C09K11/06
Inventor 刘路琦吕宏光赵晓伟
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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