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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 |
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| Authors: | Jian-Feng ZhaoLin Chen Peng-Ju SunXiao-Ya Hou Xiang-Hua ZhaoWei-Jie Li Ling-Hai Xie Yan QianNai-En Shi Wen-Yong LaiQu-Li Fan Wei Huang |
| Institution: | Key Laboratory for Organic Electronics and Information Displays (KLOEID), Institute of Advanced Materials (IAM), Nanjing University of Posts and Telecommunications, Nanjing 210046, China |
| Abstract: | 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. |
| Keywords: | One-pot synthesis 2-Bromo-4 5-diazafluoren-9-one Tandem oxidation-bromination-rearrangement Donor-acceptor Organic semiconductor |
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