4-(1-(2-hexyldecyl)-1H-phenanthro[1,10,9,8-cdefg]carbazol-3-yl)benzoic acid | 1234195-79-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(1-(2-hexyldecyl)-1H-phenanthro[1,10,9,8-cdefg]carbazol-3-yl)benzoic acid
• CAS: 1234195-79-9
• 化学式: C₄₃H₄₇NO₂
• 分子量: 609.852
• InChiKey: DULLLNKVXJNJFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.83
• 重原子数：
  46.0
• 可旋转键数：
  16.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  42.23
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-癸基-1-十四醇 、 4-(1-(2-hexyldecyl)-1H-phenanthro[1,10,9,8-cdefg]carbazol-3-yl)benzoic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以86%的产率得到2-decyltetradecyl 4-(1-(2-hexyldecyl)-1H-phenanthro[1,10,9,8-cdefg]carbazol-3-yl)benzoate
  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：

  Methyl 4-[12-(2-hexyldecyl)-12-azahexacyclo[11.8.0.02,11.03,8.04,20.016,21]henicosa-1(13),2(11),3,5,7,9,14,16(21),17,19-decaen-9-yl]benzoate 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4-(1-(2-hexyldecyl)-1H-phenanthro[1,10,9,8-cdefg]carbazol-3-yl)benzoic 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