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Fluorenyl-[beta]-carboline compound, application thereof as organic light-emitting material and aggregation-induced emission enhancement material, and preparation method of the compound

A technology for aggregation-induced fluorescence and light-emitting materials, applied in the field of organic light-emitting materials, can solve the problems of few types of compounds, poor structural modifiability, complicated device preparation, etc., and achieves the effects of good film formation, few synthesis steps, and easy purification.

Active Publication Date: 2016-08-10
INST OF ANALYSIS GUANGDONG ACAD OF SCI (CHINA NAT ANALYTICAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Furthermore, this type of material also has disadvantages such as fewer types of compounds, poor structural modification, and complicated device preparation.

Method used

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  • Fluorenyl-[beta]-carboline compound, application thereof as organic light-emitting material and aggregation-induced emission enhancement material, and preparation method of the compound
  • Fluorenyl-[beta]-carboline compound, application thereof as organic light-emitting material and aggregation-induced emission enhancement material, and preparation method of the compound
  • Fluorenyl-[beta]-carboline compound, application thereof as organic light-emitting material and aggregation-induced emission enhancement material, and preparation method of the compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Example 1: Preparation of N'-(2-fluorenylidene)-β-carboline-3-formylhydrazide (I)

[0053] (1) Preparation of β-carboline-3-formylhydrazide (compound III)

[0054] In a 100 ml round bottom flask, dissolve ethyl β-carboline-3-carboxylate (compound II) and hydrazine hydrate (80%) at a weight ratio of 1:5 in 50 ml of methanol, and reflux under rapid stirring After 7 hours, after the reaction was completed, it was cooled to room temperature, and the obtained solid matter was suction-filtered under reduced pressure, washed with water three times, and dried at room temperature. Recrystallized from ethanol and dried in vacuo to obtain β-carboline-3-carboxylhydrazide (compound III) in the form of silvery white flakes, with a yield of 82%, ESI-MS m / z: 227.3 (M+H) + ;

[0055] (2) Preparation of N'-(2-fluorenylidene)-β-carboline-3-formylhydrazide (compound I)

[0056] In a dry 100 ml round bottom flask, add intermediate β-carboline-3-formylhydrazide (compound III) (0.002mol), ...

Embodiment 2

[0058] Example 2: Preparation of N'-(2-fluorenylidene)-β-carboline-3-formylhydrazide (I)

[0059] According to the method of embodiment 1, obtain by two-step reaction, difference is, in step (1), the weight ratio of β-carboline-3-formic acid ethyl ester and hydrazine hydrate (80%) is 1:9, reaction The organic solvent used is ethanol, the reaction time is 9 hours, and the productive rate is 84%; The reaction was stirred and refluxed for 8 hours, and the mixed solvent used for recrystallization was ethanol-acetone. Yield 87%.

Embodiment 3

[0060] Example 3: Preparation of N'-(2-fluorenylidene)-β-carboline-3-formylhydrazide (I)

[0061] According to the method of embodiment 1, obtain by two-step reaction, difference is, in step (1), the weight ratio of β-carboline-3-formic acid ethyl ester and hydrazine hydrate (80%) is 1:7, reaction The organic solvent used is ethanol, the reaction time is 8 hours, and the productive rate is 83%; The reaction was stirred and refluxed for 7 hours, and the mixed solvent used for recrystallization was ethanol-acetone. Yield 85%.

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Abstract

The invention discloses a fluorenyl-[beta]-carboline compound, an application thereof as an organic light-emitting material and an aggregation-induced emission enhancement material, and a preparation method of the compound. In the invention, two functional structure units, [beta]-carboline and fluorene, are bonded to each other through an acylhydrazone bridge bond to obtain the novel fluorenyl-[beta]-carboline organic light-emitting molecule. The compound has dual-emission and aggregation-induced emission enhancement characters, has stable structure, is not liable to crystallize, is good in film-forming property and has strong practicability. The preparation method employs low-cost and easy-to-obtained raw materials, is less in synthetic steps, is simple in operations, is simple in purification and is easy to achieve industrial production.

Description

Technical field: [0001] The invention relates to the technical field of organic luminescent materials, in particular to a fluorenyl β-carboline compound, its application and preparation method as an organic luminescent material and an aggregation-induced fluorescence enhancing material. Background technique: [0002] Organic light-emitting materials are widely used in many fields such as organic fluorescent sensors, organic optoelectronic devices, and bioluminescent imaging. The most prominent feature of organic light-emitting materials is that they can convert various forms of absorbed energy into optical radiation. One of the key issues to be solved in the development of organic light-emitting materials is how to improve the solid-state emission properties of organic materials, because in most cases, although organic light-emitting materials show strong fluorescence in dilute solutions, they often fluoresce in solid or aggregated states. Quenching, there is only weak fluor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C09K11/06
CPCC07D471/04C09K11/06C09K2211/1022C09K2211/1029
Inventor 汪昭玮马艳芳孙一峰叶小机吉国强林文潘文龙牟德海陈江韩
Owner INST OF ANALYSIS GUANGDONG ACAD OF SCI (CHINA NAT ANALYTICAL
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