2-Decyltetradecyl 4-[15-[15-[15-[4-(2-decyltetradecoxycarbonyl)phenyl]-12-(2-hexyldecyl)-12-azahexacyclo[11.8.0.02,11.03,8.04,20.016,21]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaen-9-yl]-12-(2-hexyldecyl)-12-azahexacyclo[11.8.0.02,11.03,8.04,20.016,21]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaen-9-yl]-12-(2-hexyldecyl)-12-azahexacyclo[11.8.0.02,11.03,8.04,20.016,21]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaen-9-yl]benzoate | 1220707-54-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-Decyltetradecyl 4-[15-[15-[15-[4-(2-decyltetradecoxycarbonyl)phenyl]-12-(2-hexyldecyl)-12-azahexacyclo[11.8.0.02,11.03,8.04,20.016,21]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaen-9-yl]-12-(2-hexyldecyl)-12-azahexacyclo[11.8.0.02,11.03,8.04,20.016,21]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaen-9-yl]-12-(2-hexyldecyl)-12-azahexacyclo[11.8.0.02,11.03,8.04,20.016,21]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaen-9-yl]benzoate
• 英文别名: 2-decyltetradecyl 4-[15-[15-[15-[4-(2-decyltetradecoxycarbonyl)phenyl]-12-(2-hexyldecyl)-12-azahexacyclo[11.8.0.02,11.03,8.04,20.016,21]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaen-9-yl]-12-(2-hexyldecyl)-12-azahexacyclo[11.8.0.02,11.03,8.04,20.016,21]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaen-9-yl]-12-(2-hexyldecyl)-12-azahexacyclo[11.8.0.02,11.03,8.04,20.016,21]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaen-9-yl]benzoate
• CAS: 1220707-54-9
• 化学式: C₁₇₀H₂₂₉N₃O₄
• 分子量: 2378.71
• InChiKey: GZCRDFOXRWFWLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  65.6
• 重原子数：
  177
• 可旋转键数：
  94
• 环数：
  20.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Decyltetradecyl 4-[15-[15-[15-[4-(2-decyltetradecoxycarbonyl)phenyl]-12-(2-hexyldecyl)-12-azahexacyclo[11.8.0.02,11.03,8.04,20.016,21]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaen-9-yl]-12-(2-hexyldecyl)-12-azahexacyclo[11.8.0.02,11.03,8.04,20.016,21]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaen-9-yl]-12-(2-hexyldecyl)-12-azahexacyclo[11.8.0.02,11.03,8.04,20.016,21]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaen-9-yl]benzoate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以65%的产率得到
  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-(2-exyldecyl)-3,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-phenanthro[1,10,9,8-cdefg]carbazole 、 2-Decyltetradecyl 4-[15-bromo-12-(2-hexyldecyl)-12-azahexacyclo[11.8.0.02,11.03,8.04,20.016,21]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaen-9-yl]benzoate 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 以72%的产率得到2-Decyltetradecyl 4-[15-[15-[15-[4-(2-decyltetradecoxycarbonyl)phenyl]-12-(2-hexyldecyl)-12-azahexacyclo[11.8.0.02,11.03,8.04,20.016,21]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaen-9-yl]-12-(2-hexyldecyl)-12-azahexacyclo[11.8.0.02,11.03,8.04,20.016,21]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaen-9-yl]-12-(2-hexyldecyl)-12-azahexacyclo[11.8.0.02,11.03,8.04,20.016,21]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaen-9-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

文献信息

• 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.