6,11,21,26,36,41-Hexadodecyl-5,12,15,20,27,30,35,42,45-nonathiatridecacyclo[30.13.0.02,16.03,14.04,8.09,13.017,31.018,29.019,23.024,28.033,44.034,38.039,43]pentatetraconta-1,3,6,8,10,13,16,18,21,23,25,28,31,33,36,38,40,43-octadecaene | 1498410-81-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 6,11,21,26,36,41-Hexadodecyl-5,12,15,20,27,30,35,42,45-nonathiatridecacyclo[30.13.0.02,16.03,14.04,8.09,13.017,31.018,29.019,23.024,28.033,44.034,38.039,43]pentatetraconta-1,3,6,8,10,13,16,18,21,23,25,28,31,33,36,38,40,43-octadecaene
• 英文别名: 6,11,21,26,36,41-hexadodecyl-5,12,15,20,27,30,35,42,45-nonathiatridecacyclo[30.13.0.02,16.03,14.04,8.09,13.017,31.018,29.019,23.024,28.033,44.034,38.039,43]pentatetraconta-1,3,6,8,10,13,16,18,21,23,25,28,31,33,36,38,40,43-octadecaene
• CAS: 1498410-81-3
• 化学式: C₁₀₈H₁₅₆S₉
• 分子量: 1743.02
• InChiKey: YFJLQEIMQUXODG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  51.5
• 重原子数：
  117
• 可旋转键数：
  66
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  254
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  在 iron(III) chloride 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 反应 0.13h， 以76%的产率得到6,11,21,26,36,41-Hexadodecyl-5,12,15,20,27,30,35,42,45-nonathiatridecacyclo[30.13.0.02,16.03,14.04,8.09,13.017,31.018,29.019,23.024,28.033,44.034,38.039,43]pentatetraconta-1,3,6,8,10,13,16,18,21,23,25,28,31,33,36,38,40,43-octadecaene
  参考文献：
  名称：

  Propeller-Shaped Fused Oligothiophenes: A Remarkable Effect of the Topology of Sulfur Atoms on Columnar Stacking

  摘要：

  Propeller-shaped regioisomers of fused oligothiophenes F9T(endo), F9T(anti), and F9T(exo) were successfully synthesized. DFT calculations indicated that their core parts are distorted from planarity due to intramolecular steric repulsions involving large sulfur atoms. In contrast with soft crystalline F9T(anti), and F9T(exo), F9T(endo) self-assembles into a hexagonal columnar liquid crystal (Col(h) LC), displaying a clear X-ray diffraction (XRD) due to its stacked pi-conjugated core. In each LC column, well-organized intermolecular S-S contacts are developed triple-helically along the columnar axis with a helical pitch of 4.04 nm. Among LC semiconductors reported to date, Col(h) LC F9T(endo), displays a top-class charge-carrier mobility (0.18 cm(2) V-1 s(-1)) with a distinct ambipolar character featuring well-balanced hole and electron mobilities. A thin film, prepared by mixing F9T(endo) with soluble fullerene PCBM, shows a photovoltaic response, when the fullerene content is large enough to compensate a small absorptivity of F9T(endo) for visible light.

  DOI：

  10.1021/ja4092769

文献信息

• Propeller-Shaped Fused Oligothiophenes: A Remarkable Effect of the Topology of Sulfur Atoms on Columnar Stacking
  作者：Qi Xiao、Tsuneaki Sakurai、Takahiro Fukino、Kouki Akaike、Yoshihito Honsho、Akinori Saeki、Shu Seki、Kenichi Kato、Masaki Takata、Takuzo Aida

  DOI：10.1021/ja4092769

  日期：2013.12.11

  Propeller-shaped regioisomers of fused oligothiophenes F9T(endo), F9T(anti), and F9T(exo) were successfully synthesized. DFT calculations indicated that their core parts are distorted from planarity due to intramolecular steric repulsions involving large sulfur atoms. In contrast with soft crystalline F9T(anti), and F9T(exo), F9T(endo) self-assembles into a hexagonal columnar liquid crystal (Col(h) LC), displaying a clear X-ray diffraction (XRD) due to its stacked pi-conjugated core. In each LC column, well-organized intermolecular S-S contacts are developed triple-helically along the columnar axis with a helical pitch of 4.04 nm. Among LC semiconductors reported to date, Col(h) LC F9T(endo), displays a top-class charge-carrier mobility (0.18 cm(2) V-1 s(-1)) with a distinct ambipolar character featuring well-balanced hole and electron mobilities. A thin film, prepared by mixing F9T(endo) with soluble fullerene PCBM, shows a photovoltaic response, when the fullerene content is large enough to compensate a small absorptivity of F9T(endo) for visible light.