Ni-catalyzed cascade coupling reactions: synthesis and thermally-activated delayed fluorescence characterization of quinazolinone derivatives

A nickel-catalyzed strategy for the synthesis of 1,3-diaryl-6 H -pyrazino[2,1- b ]quinazolin-6-one was developed. This method enabled us to access valuable pyrazino-fused quinazolinones with tolerance of many functional groups even at room temperature. The desired pyrazino-fused quinazolinones emit...

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Bibliographic Details
Published in:New journal of chemistry 2021-11, Vol.45 (44), p.2624-2628
Main Authors: Chen, Lepeng, Zhang, Shou-Feng, Chen, Zhongyan, Zhen, Qianqian, Xiong, Wenzhang, Shao, Yinlin, Ge, Jing-Yuan, Lv, Ningning, Chen, Jiuxi
Format: Article
Language:English
Subjects:
Cascade chemical reactions
Chemical reactions
Chemical synthesis
Coupling (molecular)
Fluorescence
Functional groups
Nickel
Optoelectronics
Quinazolinones
Room temperature
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Summary:A nickel-catalyzed strategy for the synthesis of 1,3-diaryl-6 H -pyrazino[2,1- b ]quinazolin-6-one was developed. This method enabled us to access valuable pyrazino-fused quinazolinones with tolerance of many functional groups even at room temperature. The desired pyrazino-fused quinazolinones emit strongly in both solution and solid states. Furthermore, the thermally-activated delayed fluorescence (TADF) of 3a was investigated. This study provides an efficient synthetic route for the development of TADF-active pyrazino-fused quinazolinones, thus expanding the application range of this versatile molecular scaffold in optoelectronics. A nickel-catalyzed cascade coupling of 2-(2-(arylcarbonyl)-4-oxoquinazolin-3(4 H )-yl)acetonitrile and arylboronic acid for the synthesis of pyrazino-fused quinazolinones has been developed. The TADF effect of 3a in the solid-state was investigated.
ISSN:1144-0546
1369-9261
DOI:10.1039/d1nj02871e