One-pot synthesis of 2-bromo-4,5-diazafluoren-9-one via a tandem oxidation-bromination-rearrangement of phenanthroline and its hammer-shaped donor-acceptor organic semiconductors

Jian Feng Zhao, Lin Chen, Peng Ju Sun, Xiao Ya Hou, Xiang Hua Zhao, Wei Jie Li, Ling Hai Xie, Yan Qian, Nai En Shi, Wen Yong Lai, Qu Li Fan, Wei Huang

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摘要

An unexpected one-pot tandem procedure of 2-bromo-4,5-diazafluoren-9-one starting from phenanthroline with a yield of up to 50% has been described. The conversion mechanism involves three consecutive oxidation, bromination, and rearrangement reactions. A series of its hammer-shaped donor-acceptor organic semiconductors with solvent-dependent fluorescence have also been constructed via Ullman and/or Friedel-Crafts reaction. Diazafluorenes (DAFs) and derivatives are regarded as promising building blocks or candidates for donor-acceptor organic semiconductors.

源语言英语
页(从-至)1977-1982
页数6
期刊Tetrahedron
67
10
DOI
出版状态已出版 - 11 3月 2011
已对外发布

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