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

详细信息    查看全文

• 作者：Jian-Feng Zhao^a ; Lin Chen^a ; Peng-Ju Sun^a ; Xiao-Ya Hou^a ; Xiang-Hua Zhao^a ; Wei-Jie Li^a ; Ling-Hai Xie ; ^a ; ^{iamlhxie@njupt.edu.cn} ; Yan Qian^a ; Nai-En Shi^a ; Wen-Yong Lai^a ; Qu-Li Fan^a ; Wei Huang ; ^a ; ^{iamwhuang@njupt.edu.cn}
• 关键词：One-pot synthesis ; 2-Bromo-4 ; 5-diazafluoren-9-one ; Tandem oxidation&#x2013 ; bromination-rearrangement ; Donor&#x2013 ; acceptor ; Organic semiconductor
• 刊名：Tetrahedron
• 出版年：2011
• 出版时间：11 March 2011
• 年：2011
• 卷：67
• 期：10
• 页码：1977-1982
• 全文大小：750 K

文摘

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.