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 | 1220707-45-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 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
• 英文别名: 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
• CAS: 1220707-45-8
• 化学式: C₄₄H₄₉NO₂
• 分子量: 623.879
• InChiKey: UPMHDTGYBDSFJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.7
• 重原子数：
  47
• 可旋转键数：
  17
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1-溴-2-己基癸烷 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 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
  参考文献：
  名称：

  Columnar liquid crystalline bis-N-annulated quaterrylenes

  摘要：

  通过 DDQ/Sc(OTf)3氧化偶联和环融合，从容易获得的 N-annulated 四烯制备出了柱状液晶双 N-annulated 四烯。

  DOI：

  10.1039/c1cc13398e

文献信息

• Columnar liquid crystalline bis-N-annulated quaterrylenes
  作者：Yan Li、Linxiao Hao、Hongbing Fu、Wojciech Pisula、Xinliang Feng、Zhaohui Wang

  DOI：10.1039/c1cc13398e

  日期：——

  Columnar liquid crystalline bis-N-annulated quaterrylenes have been prepared from readily available N-annulated perylenes by DDQ/Sc(OTf)3 oxidative coupling and ring-fusion.

  通过 DDQ/Sc(OTf)3氧化偶联和环融合，从容易获得的 N-annulated 四烯制备出了柱状液晶双 N-annulated 四烯。
• Tri-N-annulated Hexarylene: An Approach to Well-Defined Graphene Nanoribbons with Large Dipoles
  作者：Yan Li、Jing Gao、Simone Di Motta、Fabrizia Negri、Zhaohui Wang

  DOI：10.1021/ja100276x

  日期：2010.3.31

  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.