1,4-bis(4-tert-butylphenyl)-2,3-bis(4-dodecylphenyl)-5,6-bis[4-(trimethylsilyl)biphenyl]benzene | 816466-86-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1,4-bis(4-tert-butylphenyl)-2,3-bis(4-dodecylphenyl)-5,6-bis[4-(trimethylsilyl)biphenyl]benzene
• 英文别名: [4-[4-[2,5-Bis(4-tert-butylphenyl)-3,4-bis(4-dodecylphenyl)-6-[4-(4-trimethylsilylphenyl)phenyl]phenyl]phenyl]phenyl]-trimethylsilane
• CAS: 816466-86-1
• 化学式: C₉₂H₁₁₈Si₂
• 分子量: 1280.12
• InChiKey: UIBMHYXTTZFFLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  27.63
• 重原子数：
  94
• 可旋转键数：
  34
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,4-bis(4-tert-butylphenyl)-2,3-bis(4-dodecylphenyl)-5,6-bis[4-(trimethylsilyl)biphenyl]benzene 在 一氯化碘 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 0.75h， 以92%的产率得到1,4-bis(4-tert-butylphenyl)-2,3-bis(4-dodecylphenyl)-5,6-bis[4-iodo-4'-biphenyl]benzene
  参考文献：
  名称：

  Oligomers of Hexa-peri-hexabenzocoronenes as “Super-oligophenylenes”:  Synthesis, Electronic Properties, and Self-assembly

  摘要：

  Hexa-peri-hexabenzocoronene (HBC) is a remarkable polycyclic aromatic hydrocarbon and is often called "superbenzene" because of its similarity to benzene. In this article we present the facile synthesis of oligomers of HBC, up to trimers (3, 4, 5a-c) with different modes of connection. UV-vis and fluorescence spectroscopy studies reveal that the oligomers are electronically decoupled. This arises from the small atomic orbital coefficients of the bridge-head carbon atoms, the large torsion angle between the HBC units, and the large distance of interacting transition dipoles due to the size of the HBC chromophore. For comparison, a methylene-bridged HBC dimer 6, so-called "superfluorene", was prepared. The induced planarity improves pi-conjugation and suppresses the geometrical relaxation of the backbone upon electronic excitation, leading to a prominent 0-0 transition band in the fluorescence spectra. The self-assembly of the oligomers and of superfluorene 6 was studied by wide-angle X-ray diffraction (WAXD) in the bulk state, and ordered columnar stacking occurs in the HBC dimer 3, p-HBC trimer 4, and superfluorene 6. Measurements of shear-aligned samples show that, despite increasing aspects ratio by linear entrainment of disks, the anitropic element that is subject to alignment by shear is the supramolecular columns.

  DOI：

  10.1021/jo0490301
• 作为产物：
  描述：

  二(4-溴苯基)乙炔 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 二苯醚 、 水 、 甲苯 为溶剂， 反应 41.0h， 生成 1,4-bis(4-tert-butylphenyl)-2,3-bis(4-dodecylphenyl)-5,6-bis[4-(trimethylsilyl)biphenyl]benzene
  参考文献：
  名称：

  Oligomers of Hexa-peri-hexabenzocoronenes as “Super-oligophenylenes”:  Synthesis, Electronic Properties, and Self-assembly

  摘要：

  Hexa-peri-hexabenzocoronene (HBC) is a remarkable polycyclic aromatic hydrocarbon and is often called "superbenzene" because of its similarity to benzene. In this article we present the facile synthesis of oligomers of HBC, up to trimers (3, 4, 5a-c) with different modes of connection. UV-vis and fluorescence spectroscopy studies reveal that the oligomers are electronically decoupled. This arises from the small atomic orbital coefficients of the bridge-head carbon atoms, the large torsion angle between the HBC units, and the large distance of interacting transition dipoles due to the size of the HBC chromophore. For comparison, a methylene-bridged HBC dimer 6, so-called "superfluorene", was prepared. The induced planarity improves pi-conjugation and suppresses the geometrical relaxation of the backbone upon electronic excitation, leading to a prominent 0-0 transition band in the fluorescence spectra. The self-assembly of the oligomers and of superfluorene 6 was studied by wide-angle X-ray diffraction (WAXD) in the bulk state, and ordered columnar stacking occurs in the HBC dimer 3, p-HBC trimer 4, and superfluorene 6. Measurements of shear-aligned samples show that, despite increasing aspects ratio by linear entrainment of disks, the anitropic element that is subject to alignment by shear is the supramolecular columns.

  DOI：

  10.1021/jo0490301

文献信息

• Oligomers of Hexa-<i>p</i><i>eri</i>-hexabenzocoronenes as “Super-oligophenylenes”:  Synthesis, Electronic Properties, and Self-assembly
  作者：Jishan Wu、Mark D. Watson、Natalia Tchebotareva、Zhaohui Wang、Klaus Müllen

  DOI：10.1021/jo0490301

  日期：2004.11.1

  Hexa-peri-hexabenzocoronene (HBC) is a remarkable polycyclic aromatic hydrocarbon and is often called "superbenzene" because of its similarity to benzene. In this article we present the facile synthesis of oligomers of HBC, up to trimers (3, 4, 5a-c) with different modes of connection. UV-vis and fluorescence spectroscopy studies reveal that the oligomers are electronically decoupled. This arises from the small atomic orbital coefficients of the bridge-head carbon atoms, the large torsion angle between the HBC units, and the large distance of interacting transition dipoles due to the size of the HBC chromophore. For comparison, a methylene-bridged HBC dimer 6, so-called "superfluorene", was prepared. The induced planarity improves pi-conjugation and suppresses the geometrical relaxation of the backbone upon electronic excitation, leading to a prominent 0-0 transition band in the fluorescence spectra. The self-assembly of the oligomers and of superfluorene 6 was studied by wide-angle X-ray diffraction (WAXD) in the bulk state, and ordered columnar stacking occurs in the HBC dimer 3, p-HBC trimer 4, and superfluorene 6. Measurements of shear-aligned samples show that, despite increasing aspects ratio by linear entrainment of disks, the anitropic element that is subject to alignment by shear is the supramolecular columns.