12-(2-Hexyldecyl)-9-naphthalen-1-yl-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-decaene | 1131759-20-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 12-(2-Hexyldecyl)-9-naphthalen-1-yl-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-decaene
• CAS: 1131759-20-0
• 化学式: C₄₆H₄₉N
• 分子量: 615.902
• InChiKey: GCXBKGYNVGLOKV-UHFFFAOYSA-N

物化性质

• 沸点：
  738.9±53.0 °C(predicted)
• 密度：
  1.11±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  16.1
• 重原子数：
  47
• 可旋转键数：
  15
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  12-(2-Hexyldecyl)-9-naphthalen-1-yl-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-decaene 在 一水合肼 、 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23%的产率得到5,38-Bis(2-hexyldecyl)-8,35-dinaphthalen-1-yl-5,38-diazatridecacyclo[20.18.1.12,17.04,16.06,15.09,14.013,18.025,30.026,41.027,39.028,37.029,34.021,42]dotetraconta-1(40),2,4(16),6(15),7,9,11,13,17,19,21(42),22(41),23,25,27(39),28(37),29,31,33,35-icosaene
  参考文献：
  名称：

  Bis-N-Annulated Quaterrylene: An Approach to Processable Graphene Nanoribbons

  摘要：

  A new efficient synthetic method toward processable bis-N-annulated quaterrylene from easily available N-annulated perylene derivatives, which is conducted by DDQ/Sc(OTf)(3) oxidative coupling and ring fusion, is reported. In light of the good processability and the strong electron-donating ability, which is evidenced from the low oxidative potentials, bis-N-annulated quaterrylene is very promising for use as functional components in molecular devices.

  DOI：

  10.1021/ol9002064
• 作为产物：
  描述：

  3-bromo-1-(2-hexyldecyl)-1H-phenanthro[1,10,9,8-cdefg]carbazole 、 1-萘硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以90%的产率得到12-(2-Hexyldecyl)-9-naphthalen-1-yl-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-decaene
  参考文献：
  名称：

  Bis-N-Annulated Quaterrylene: An Approach to Processable Graphene Nanoribbons

  摘要：

  A new efficient synthetic method toward processable bis-N-annulated quaterrylene from easily available N-annulated perylene derivatives, which is conducted by DDQ/Sc(OTf)(3) oxidative coupling and ring fusion, is reported. In light of the good processability and the strong electron-donating ability, which is evidenced from the low oxidative potentials, bis-N-annulated quaterrylene is very promising for use as functional components in molecular devices.

  DOI：

  10.1021/ol9002064

文献信息

• Bis-N-Annulated Quaterrylene: An Approach to Processable Graphene Nanoribbons
  作者：Yan Li、Zhaohui Wang

  DOI：10.1021/ol9002064

  日期：2009.3.19

  A new efficient synthetic method toward processable bis-N-annulated quaterrylene from easily available N-annulated perylene derivatives, which is conducted by DDQ/Sc(OTf)(3) oxidative coupling and ring fusion, is reported. In light of the good processability and the strong electron-donating ability, which is evidenced from the low oxidative potentials, bis-N-annulated quaterrylene is very promising for use as functional components in molecular devices.
• 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.