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9,10-diarylethene anthracene (CPASA) aggregation-induced light emitting molecule and preparation method thereof

A diaryl vinyl anthracene, aggregation-induced luminescence technology, applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve problems such as unfavorable fluorescence emission, application limitations of fluorescent molecules, and weakened fluorescence

Inactive Publication Date: 2014-07-02
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Most fluorescent chromophores have good luminescent properties in dilute solutions, but in the aggregated state, due to intermolecular interactions, non-radiative energy conversion or species that are not conducive to fluorescence emission are formed, resulting in weakened fluorescence or even aggregation without luminescence. The phenomenon of fluorescence quenching, which greatly limits the application of fluorescent molecules

Method used

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  • 9,10-diarylethene anthracene (CPASA) aggregation-induced light emitting molecule and preparation method thereof
  • 9,10-diarylethene anthracene (CPASA) aggregation-induced light emitting molecule and preparation method thereof
  • 9,10-diarylethene anthracene (CPASA) aggregation-induced light emitting molecule and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1. 9,10-diarylvinylanthracene aggregation-induced luminescent molecule 9,10-bis{4-{N,N-bis[4-(carbazol-9-yl)phenyl]amino}styryl} The preparation method of anthracene CPASA

[0018] (1) 9,10-bis{4 -[N,N-bis(4-iodophenyl)amino]styryl}anthracene (SM), the synthetic route is as follows:

[0019]

[0020] For the specific preparation method, refer to a pyridine-triphenylamine-anthracene conjugated molecule with aggregation-induced luminescent properties and its preparation publication No. CN103524404A Example 1.

[0021] (2) 9,10-bis{4-[N,N-bis(4-iodophenyl)amino]styryl}anthracene (SM) reacts with carbazole at a molar ratio of 1:6 to obtain 9,10- Bis{4-{N,N-bis[4-(carbazol-9-yl)phenyl]amino}styryl}anthracene (CPASA), the synthetic route is as follows:

[0022]

[0023] The specific preparation method is: under anhydrous and oxygen-free conditions, weigh 1.00g (5.98mmol) of carbazole and dissolve it in 10mL of N,N-dimethylacetamide, add 0.78g (4.01mmol) of cu...

Embodiment 2

[0029] Example 2.9,10-Diarylvinylanthracene CPASA solid-state fluorescence

[0030] 9,10-Diarylvinylanthracene CPASA emits yellow light in solid state with a maximum emission wavelength of 581nm. The solid state of CPASA emits bright yellow fluorescence under ultraviolet light in a dark room. attached figure 1 Fluorescence of 9,10-bis{4-{N,N-bis[4-(carbazol-9-yl)phenyl]amino}styryl}anthracene (CPASA) solid powder prepared for Example 1 of the present invention spectrum.

Embodiment 3

[0031] Example 3.9, Aggregation-induced fluorescence enhancement of 10-diarylvinylanthracene CPASA

[0032] 9,10-Diarylvinylanthracene CPASA is insoluble in water, but soluble in organic solvents such as dimethylformamide, tetrahydrofuran, chloroform, dichloromethane, ethyl acetate, and acetone. It does not emit light in organic solvents such as dimethylformamide, and has no fluorescence under ultraviolet light in a dark room, but the fluorescence increases rapidly after adding 20% ​​water by volume, and emits bright yellow fluorescence. attached figure 2 9,10-bis{4-{N,N-bis[4-(carbazol-9-yl)phenyl]amino}styryl}anthracene (CPASA) prepared in Example 1 of the present invention in water / di Fluorescence emission intensity changes in methylformamide mixed solutions with different water contents.

[0033] The 9,10-diarylvinylanthracene CPASA of the present invention has aggregation-induced luminescent properties, and has important application value in the fields of fluorescent s...

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Abstract

The invention discloses a 9,10-diarylethene anthracene (CPASA) aggregation-induced light emitting molecule, namely 9,10-bis{4-{N,N-di[4-(carbazole-9-yl)phenyl]amino}styryl}anthracene, yellow light is emitted in a solid state, and the maximum emission wavelength is 581nm. The compound CPASA is not dissolved in water but in organic solvents such as dimethyl formamide, tetrahydrofuran, chloroform, dichloromethane, ethyl acetate and acetone, does not emit light in organic solvents like dimethyl formamide and emits yellow fluorescent light in a water / dimethyl formamide mixed solvent, and the fluorescent light in the water / dimethyl formamide mixed solvent with the water content of 20% is the strongest. The CPASA has aggregation-induced light emitting property and has important application value in the fields of fluorescent switches and sensors, fluorescent probes, biomarkers and fluorescent imaging, organic light emitting devices and the like.

Description

technical field [0001] The invention relates to a 9,10-diarylvinylanthracene aggregation-induced luminescence molecule and a preparation method thereof, in particular to a 9,10-bis{4-{N,N-bis[4-(carbazol-9-yl )Phenyl]amino}styryl}anthracene (CPASA) and process for its preparation. Background technique [0002] Most fluorescent chromophores have good luminescent properties in dilute solutions, but in the aggregated state, due to intermolecular interactions, non-radiative energy conversion or species that are not conducive to fluorescence emission are formed, resulting in weakened fluorescence or even aggregation without luminescence. The phenomenon of fluorescence quenching greatly limits the application of fluorescent molecules. [0003] Regulate the aggregation state of molecules by means of intramolecular rotation limitation, intramolecular coplanarity, formation of J-aggregates and special excimer associations, etc., to solve the problem of fluorescence quenching caused ...

Claims

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Application Information

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IPC IPC(8): C07D209/86C09K11/06
CPCC07D209/86C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029
Inventor 钱鹰夏超管成飞
Owner SOUTHEAST UNIV
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