A fluorenyl β-carboline compound, its application and preparation method as an organic light-emitting material and an aggregation-induced fluorescence enhancement material

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, complex device preparation, etc., and achieves the effects of good film formation, few synthesis steps, and easy purification.

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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, complex device preparation, etc., and achieves the effects of good film formation, few synthesis steps, and easy purification.

CN105837568BActive Publication Date: 2018-02-23INSTITUTE OF ANALYSIS GUANGDONG ACADEMY OF SCIENCES (CHINA NATIONAL ANALYTICAL CENTER GUANGZHOU)

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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

Patent Timeline

23 Feb 2018

Publication

CN105837568B

IPC: C07D471/04; C09K11/06

CPC: C07D471/04; C09K11/06; C09K2211/1022; C09K2211/1029

Inventors: 汪昭玮; 马艳芳