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Rhodamine b derivatives with solid-state luminescent properties and their preparation and application

A technology of solid-state luminescence and derivatives, applied in the direction of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems that cannot be applied to living organisms, achieve the effects of reducing complexity, avoiding adsorption loss, and increasing flexibility

Active Publication Date: 2017-12-01
SHANGHAI JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the inherent luminescent properties of the compound, traditional rhodamine B derivatives can emit light in solution as a fluorescent probe, but the phenomenon of luminescence disappearing in the aggregated or crystalline state, that is, fluorescence quenching, has not been obtained in the above patents. good solution
Therefore, such fluorescent probes can only be applied to the detection of ions in dilute solutions, but cannot be applied to living organisms, crystalline responses, nanoparticles, etc.

Method used

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  • Rhodamine b derivatives with solid-state luminescent properties and their preparation and application
  • Rhodamine b derivatives with solid-state luminescent properties and their preparation and application
  • Rhodamine b derivatives with solid-state luminescent properties and their preparation and application

Examples

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Effect test

Embodiment 1

[0041] Preparation method of rhodamine B derivatives with high-efficiency solid-state luminescent properties:

[0042] 1. Ethanol esterification protection: Add 17.62 mmol of 3-bromophthalic anhydride to 428.71 mmol of absolute ethanol, drop in 2 ml of 98% concentrated sulfuric acid, and reflux at 80°C for 8 hours under the protection of nitrogen.

[0043] Separation and purification: spin to dry the solvent, add potassium carbonate to neutralize to pH = 7, wash with water, separate the layers, extract the aqueous layer with dichloromethane, combine the organic layers, dry with anhydrous magnesium sulfate, suction filter, and spin to dry the solvent to obtain Yellow liquid product. Yield 60%.

[0044] 2. Suzuki cross-coupling: 2.32mmol of ethyl 3-bromophthalate and 2.79mmol of boric acid compound of triphenylethylene (HTPE) were added to a mixed solution of 35ml of tetrahydrofuran and 5ml of water under nitrogen protection, and 6.97mmol of Potassium carbonate and 92.98 μmol ...

Embodiment 2

[0051] Preparation method of rhodamine B derivatives with high-efficiency solid-state luminescent properties:

[0052] 1. Ethanol esterification protection: Add 17.62 mmol of 3-bromophthalic anhydride to 428.71 mmol of absolute ethanol, drop in 2 ml of 98% concentrated sulfuric acid, and reflux at 80°C for 8 hours under the protection of nitrogen.

[0053] Separation and purification: spin to dry the solvent, add potassium carbonate to neutralize to pH = 7, wash with water, separate the layers, extract the aqueous layer with dichloromethane, combine the organic layers, dry with anhydrous magnesium sulfate, suction filter, and spin to dry the solvent to obtain Yellow liquid product. Yield 60%.

[0054] 2. Suzuki cross-coupling: add 2.32mmol of ethyl 3-bromophthalate and 2.79mmol of boronic acid compound of tetraphenylethylene (TPE) to the mixed solution of 35ml tetrahydrofuran and 5ml water under the protection of nitrogen, and add 6.97mmol Potassium carbonate and 92.98 μmol ...

Embodiment 3

[0061] Preparation method of rhodamine B derivatives with high-efficiency solid-state luminescent properties:

[0062] 1. Ethanol esterification protection: Add 17.62 mmol of 3-bromophthalic anhydride to 428.71 mmol of absolute ethanol, drop in 2 ml of 98% concentrated sulfuric acid, and reflux at 80°C for 8 hours under the protection of nitrogen.

[0063] Separation and purification: spin to dry the solvent, add potassium carbonate to neutralize to pH = 7, wash with water, separate the layers, extract the aqueous layer with dichloromethane, combine the organic layers, dry with anhydrous magnesium sulfate, suction filter, and spin to dry the solvent to obtain Yellow liquid product. Yield 60%.

[0064] 2. Suzuki cross-coupling: add 2.32mmol of ethyl 3-bromophthalate and 2.79mmol of boric acid compound of triphenylcyanoacrylonitrile (TPAN) into the mixed solution of 35ml tetrahydrofuran and 5ml water under nitrogen protection, add 6.97 mmol of potassium carbonate and 92.98 μmo...

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Abstract

The invention relates to highly efficient solid-state luminescent rhodamine B derivatives and their preparation and application. Such compounds are obtained by modifying rhodamine B with aggregation-induced luminescence or crystallization-induced luminescence units. Protect 3-bromophthalic anhydride into a diester by esterification of ethanol in the synthesis, modify the diester with aggregation-induced luminescence or crystallization-induced luminescence unit, then deprotect the diester and hydrolyze it into a dicarboxylic acid, and then based on the dicarboxylic acid and m-hydroxy dicarboxylic acid Rhodamine B derivatives are synthesized from ethylaniline, which makes the reaction synthesis more purposeful and directional, reduces the number of reaction steps and by-products, and is simple to purify. The prepared rhodamine B derivatives can be used as fluorescent sensors, biological dyes, Imaging of cell staining and organic semiconductor materials.

Description

technical field [0001] The invention relates to a rhodamine B derivative, in particular to a rhodamine B derivative with high-efficiency solid-state luminescent properties and its preparation and application. Background technique [0002] Aggregation-induced quenching (ACQ) compounds, traditional light-emitting compounds, emit light well in dilute solutions. During aggregation, due to the strong π-π interaction between molecules or the existence of other excitons that are not conducive to luminescence, fluorescence quenching occurs. off. [0003] Aggregation-induced emission (AIE) refers to the phenomenon that compounds that emit poorly or no light in solution emit light in an aggregated state. It is a research hotspot in the field of advanced optoelectronic functional materials in recent years. AIE compounds (units) provide the possibility to obtain new high-efficiency solid-state light-emitting compounds, thus laying the foundation for their subsequent applications. At p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/82C07D409/10C07D405/10C09K11/06
CPCC09B11/24
Inventor 袁望章林云霄张永明陈赣
Owner SHANGHAI JIAOTONG UNIV
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