Bis(2-decyltetradecyl) 5-[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]benzene-1,3-dicarboxylate | 1220707-51-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Bis(2-decyltetradecyl) 5-[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]benzene-1,3-dicarboxylate
• 英文别名: bis(2-decyltetradecyl) 5-[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]benzene-1,3-dicarboxylate
• CAS: 1220707-51-6
• 化学式: C₉₂H₁₄₂BrNO₄
• 分子量: 1406.05
• InChiKey: FHAYFYOXAOYZNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  38.8
• 重原子数：
  98
• 可旋转键数：
  63
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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 、 Bis(2-decyltetradecyl) 5-[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]benzene-1,3-dicarboxylate 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Bis(2-decyltetradecyl) 5-[15-[15-[15-[3,5-bis(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]benzene-1,3-dicarboxylate
  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：

  bis(2-decyltetradecyl) 5-(1-(2-hexyldecyl)-1H-phenanthro[1,10,9,8-cdefg]carbazol-3-yl)isophthalate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以96%的产率得到Bis(2-decyltetradecyl) 5-[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]benzene-1,3-dicarboxylate
  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.