2-(2-(3-(9-phenyl-9H-fluoren-9-yl)-9H-carbazol-9-yl)-9H-4,5-diazafluoren-9-ylidene)malononitrile | 1280225-66-2

• 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-(9-phenyl-9H-fluoren-9-yl)-9H-carbazol-9-yl)-9H-4,5-diazafluoren-9-ylidene)malononitrile
• CAS: 1280225-66-2
• 化学式: C₄₅H₂₅N₅
• 分子量: 635.727
• InChiKey: GYDFOFYGOCQSBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.77
• 重原子数：
  50.0
• 可旋转键数：
  3.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.02
• 拓扑面积：
  78.29
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-溴-4,5-二氮杂-9-芴酮 在 copper(l) iodide 、 18-冠醚-6 、 三氟化硼乙醚 、 potassium carbonate 作用下， 以 二氯甲烷 、 二甲基亚砜 、 邻二氯苯 为溶剂， 反应 34.0h， 生成 2-(2-(3-(9-phenyl-9H-fluoren-9-yl)-9H-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