dimethyl 5-(1-(2-hexyldecyl)-1H-phenanthro[1,10,9,8-cdefg]carbazol-3-yl)isophthalate | 1220707-46-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: dimethyl 5-(1-(2-hexyldecyl)-1H-phenanthro[1,10,9,8-cdefg]carbazol-3-yl)isophthalate
• CAS: 1220707-46-9
• 化学式: C₄₆H₅₁NO₄
• 分子量: 681.915
• InChiKey: YAOSNULEMRQDLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.71
• 重原子数：
  51.0
• 可旋转键数：
  17.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  57.53
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  dimethyl 5-(1-(2-hexyldecyl)-1H-phenanthro[1,10,9,8-cdefg]carbazol-3-yl)isophthalate 在 potassium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 24.0h， 以98%的产率得到5-(1-(2-hexyldecyl)-1H-phenanthro[1,10,9,8-cdefg]carbazol-3-yl)isophthalic acid
  参考文献：
  名称：

  Tri-N-annulated Hexarylene: An Approach to Well-Defined Graphene Nanoribbons with Large Dipoles

  摘要：

  We report a highly efficient synthetic methodology toward tri-N-annulated hexarylenes from easily available N-annulated perylenes, which is favored by the oxidative ring fusion driven by DDQ/Sc(OTf)(3). To assist the characterization of the new compounds, quantum-chemical calculations of structural and spectroscopic properties have been carried out for three oligomers of N-annulated rylenes. It is shown that tri-N-annulated hexarylene dyes display remarkably large dipole moments likely associated with the formation of H aggregates, as suggested by the marked concentration dependence of the measured UV vis spectra. It is suggested that the combination of pi-pi stacking interactions and dipole dipole interactions may favor the formation of highly ordered supramolecular structures, resulting in enhanced charge carrier mobilities.

  DOI：

  10.1021/ja100276x
• 作为产物：
  描述：

  3-bromo-1-(2-hexyldecyl)-1H-phenanthro[1,10,9,8-cdefg]carbazole 、 3,5-双(甲氧基羰基)苯硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以83%的产率得到dimethyl 5-(1-(2-hexyldecyl)-1H-phenanthro[1,10,9,8-cdefg]carbazol-3-yl)isophthalate
  参考文献：
  名称：

  Tri-N-annulated Hexarylene: An Approach to Well-Defined Graphene Nanoribbons with Large Dipoles

  摘要：

  We report a highly efficient synthetic methodology toward tri-N-annulated hexarylenes from easily available N-annulated perylenes, which is favored by the oxidative ring fusion driven by DDQ/Sc(OTf)(3). To assist the characterization of the new compounds, quantum-chemical calculations of structural and spectroscopic properties have been carried out for three oligomers of N-annulated rylenes. It is shown that tri-N-annulated hexarylene dyes display remarkably large dipole moments likely associated with the formation of H aggregates, as suggested by the marked concentration dependence of the measured UV vis spectra. It is suggested that the combination of pi-pi stacking interactions and dipole dipole interactions may favor the formation of highly ordered supramolecular structures, resulting in enhanced charge carrier mobilities.

  DOI：

  10.1021/ja100276x