3,8-diiodo-5,10-dihydro-5,5,10,10-tetra(p-octylphenyl)indeno[2,1-a]indene | 1408238-81-2

• 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: 3,8-diiodo-5,10-dihydro-5,5,10,10-tetra(p-octylphenyl)indeno[2,1-a]indene
• CAS: 1408238-81-2
• 化学式: C₇₂H₉₀I₂
• 分子量: 1209.32
• InChiKey: DHDPRPFHZIYWKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  22.11
• 重原子数：
  74.0
• 可旋转键数：
  32.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  3,8-diiodo-5,10-dihydro-5,5,10,10-tetra(p-octylphenyl)indeno[2,1-a]indene 、 4,4'-[(2-ethynylphenyl)(methoxy)methylene]bis(octylbenzene) 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以0.78 g的产率得到2,7-bis({2-[methoxydi(p-octylphenyl)methyl]phenyl}ethynyl)-5,5,10,10-tetra(p-octylphenyl)-5,10-dihydroindeno[2,1-a]indene
  参考文献：
  名称：

  Carbon-Bridged Oligo(phenylenevinylene)s: Stable π-Systems with High Responsiveness to Doping and Excitation

  摘要：

  The high responsiveness of pi-conjugated materials to external stimuli, such as electrons and photons, accounts for both their utility in optoelectronic applications and their chemical instability. Extensive studies on heteroatom-stabilized pi-conjugated systems notwithstanding, it is still difficult to combine high performance and stability. We report here that carbon-bridged oligo(p-phenylenevinylene)s (COPV-n) are not only more responsive to doping and photoexcitation but also more stable than the conventional p-phenylenevinylenes and poly(3-hexylthiophene), surviving photolysis very well in air, suggesting that they could serve as building blocks for optoelectronic applications. Activation of the ground state by installation of bond angle strain toward the doped or photoexcited state and the flat, rigid, and hindered structure endows COPVs with stimuli-responsiveness and stability without recourse to heteroatoms. For example, COPV-6 can be doped with an extremely small reorganization energy and form a bipolaron delocalized over the entire it system. Applications to bulk and molecular optoelectronic devices are foreseen.

  DOI：

  10.1021/ja309318s
• 作为产物：
  描述：

  3,8-dibromo-5,10-dihydro-5,5,10,10-tetra(p-octylphenyl)-indeno[2,1-a]indene 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.5h， 以89%的产率得到3,8-diiodo-5,10-dihydro-5,5,10,10-tetra(p-octylphenyl)indeno[2,1-a]indene
  参考文献：
  名称：

  Carbon-Bridged Oligo(phenylenevinylene)s: Stable π-Systems with High Responsiveness to Doping and Excitation

  摘要：

  The high responsiveness of pi-conjugated materials to external stimuli, such as electrons and photons, accounts for both their utility in optoelectronic applications and their chemical instability. Extensive studies on heteroatom-stabilized pi-conjugated systems notwithstanding, it is still difficult to combine high performance and stability. We report here that carbon-bridged oligo(p-phenylenevinylene)s (COPV-n) are not only more responsive to doping and photoexcitation but also more stable than the conventional p-phenylenevinylenes and poly(3-hexylthiophene), surviving photolysis very well in air, suggesting that they could serve as building blocks for optoelectronic applications. Activation of the ground state by installation of bond angle strain toward the doped or photoexcited state and the flat, rigid, and hindered structure endows COPVs with stimuli-responsiveness and stability without recourse to heteroatoms. For example, COPV-6 can be doped with an extremely small reorganization energy and form a bipolaron delocalized over the entire it system. Applications to bulk and molecular optoelectronic devices are foreseen.

  DOI：

  10.1021/ja309318s