N,N'-di(4'-benzo-15-crown-5-ether)-1,7-di(4-tert-butyl-phenoxy)perylene-3,4;9,10-tetracarboxylic diimide | 1414294-27-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N,N'-di(4'-benzo-15-crown-5-ether)-1,7-di(4-tert-butyl-phenoxy)perylene-3,4;9,10-tetracarboxylic diimide
• CAS: 1414294-27-1
• 化学式: C₇₂H₇₀N₂O₁₆
• 分子量: 1219.35
• InChiKey: VEORGJFCYXFHKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.16
• 重原子数：
  90.0
• 可旋转键数：
  6.0
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  185.52
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  N,N'-di(4'-benzo-15-crown-5-ether)-1,7-di(4-tert-butyl-phenoxy)perylene-3,4;9,10-tetracarboxylic diimide 、 potassium acetate 以 甲醇 、 氯仿 为溶剂， 生成
  参考文献：
  名称：

  Effects of metal–ligand coordination on the self-assembly behaviour of a crown ether functionalised perylenetetracarboxylic diimide

  摘要：

  A novel perylenetetracarboxylic diimide (PDI) derivative, N,N'-di(4'-benzo-15-crown-5-ether)-1,7-di(4-tert-butyl-phenoxy) perylene-3,4;9,10-tetracarboxylic diimide (CRPDI), has been synthesised and characterised. Dimerisation of CRPDI is induced by the presence of K+ in CHCl3 or spontaneously occurs in methanol, as revealed by absorption and emission spectroscopy. In particular, the formation of co-facial dimer in the presence of K+ proceeds in a three-stage process, as indicated by absorption spectroscopy. The belt-and rope-like nanostructures of CRPDI fabricated from methanol and CHCl3 solution in the presence of K+ are obtained by scanning electron microscopy. Furthermore, the conductivity of the rope-like nanostructures from the cation-induced dimeric species is more than ca. 1 order of magnitude higher than the belt-like nanostructures from the solvent-induced dimeric species. The present result represents the further effort towards realisation of controlling and tuning the morphology of self-assembled nanostructures of PDI derivatives through molecular design and synthesis. It will be valuable for the design and preparation of PDI-based nano-(opto)electronic devices with good performance due to the close relationship between the molecular ordering and dimensions of nanostructures and the performance of nanodevices.

  DOI：

  10.1080/10610278.2012.731063
• 作为产物：
  描述：

  4'-氨基苯并-15-冠-5-醚 、 1,7-bis(4-tert-butylphenoxy)perylene-3,4:9,10-bis(dicarboxylic anhydride) 在 咪唑 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以10.3%的产率得到N,N'-di(4'-benzo-15-crown-5-ether)-1,7-di(4-tert-butyl-phenoxy)perylene-3,4;9,10-tetracarboxylic diimide
  参考文献：
  名称：

  Effects of metal–ligand coordination on the self-assembly behaviour of a crown ether functionalised perylenetetracarboxylic diimide

  摘要：

  A novel perylenetetracarboxylic diimide (PDI) derivative, N,N'-di(4'-benzo-15-crown-5-ether)-1,7-di(4-tert-butyl-phenoxy) perylene-3,4;9,10-tetracarboxylic diimide (CRPDI), has been synthesised and characterised. Dimerisation of CRPDI is induced by the presence of K+ in CHCl3 or spontaneously occurs in methanol, as revealed by absorption and emission spectroscopy. In particular, the formation of co-facial dimer in the presence of K+ proceeds in a three-stage process, as indicated by absorption spectroscopy. The belt-and rope-like nanostructures of CRPDI fabricated from methanol and CHCl3 solution in the presence of K+ are obtained by scanning electron microscopy. Furthermore, the conductivity of the rope-like nanostructures from the cation-induced dimeric species is more than ca. 1 order of magnitude higher than the belt-like nanostructures from the solvent-induced dimeric species. The present result represents the further effort towards realisation of controlling and tuning the morphology of self-assembled nanostructures of PDI derivatives through molecular design and synthesis. It will be valuable for the design and preparation of PDI-based nano-(opto)electronic devices with good performance due to the close relationship between the molecular ordering and dimensions of nanostructures and the performance of nanodevices.

  DOI：

  10.1080/10610278.2012.731063