2-(2-(3,6-bis(9-phenyl-fluoren-9-yl)-carbazol-9-yl)-9H-4,5-diazafluoren-9-ylidene)malononitrile | 1280225-67-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-(2-(3,6-bis(9-phenyl-fluoren-9-yl)-carbazol-9-yl)-9H-4,5-diazafluoren-9-ylidene)malononitrile
• 英文别名: 2-[5-[3,6-Bis(9-phenylfluoren-9-yl)carbazol-9-yl]-3,13-diazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-8-ylidene]propanedinitrile；2-[5-[3,6-bis(9-phenylfluoren-9-yl)carbazol-9-yl]-3,13-diazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-8-ylidene]propanedinitrile
• CAS: 1280225-67-3
• 化学式: C₆₄H₃₇N₅
• 分子量: 876.031
• InChiKey: OSYMWRXIUUIZLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.5
• 重原子数：
  69
• 可旋转键数：
  5
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  78.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(3,6-bis(9-phenyl-fluoren-9-yl)-carbazol-9-yl)-9H-4,5-diazafluoren-9-one 、 丙二腈 以 二甲基亚砜 为溶剂， 反应 5.0h， 以65%的产率得到2-(2-(3,6-bis(9-phenyl-fluoren-9-yl)-carbazol-9-yl)-9H-4,5-diazafluoren-9-ylidene)malononitrile
  参考文献：
  名称：

  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

  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. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2010.12.065

文献信息

• 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
  作者：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

  DOI：10.1016/j.tet.2010.12.065

  日期：2011.3

  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. (C) 2011 Published by Elsevier Ltd.