3,8-dibromo-5,10-dihydro-5,5,10,10-tetra(p-octylphenyl)-indeno[2,1-a]indene | 1408238-79-8

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 3,8-dibromo-5,10-dihydro-5,5,10,10-tetra(p-octylphenyl)-indeno[2,1-a]indene
• CAS: 1408238-79-8
• 化学式: C₇₂H₉₀Br₂
• 分子量: 1115.31
• InChiKey: LOTMEEGNZCSWHD-UHFFFAOYSA-N

物化性质

• 沸点：
  902.8±65.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  22.43
• 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-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
• 作为产物：
  描述：

  5,10-dihydro-5,5,10,10-tetra(p-octylphenyl)indeno[2,1-a]indene 在 CuBr₂-Al₂O₃ 作用下， 以 四氯化碳 为溶剂， 以22%的产率得到3,8-dibromo-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

文献信息

• New sensitizers for dye-sensitized solar cells featuring a carbon-bridged phenylenevinylene
  作者：Xiaozhang Zhu、Hayato Tsuji、Aswani Yella、Anne-Sophie Chauvin、Michael Grätzel、Eiichi Nakamura

  DOI：10.1039/c2cc37124c

  日期：——

  We demonstrate that a carbon-bridged phenylenevinylene (CPV)-linked dye serves as a novel and efficient sensitizer for dye-sensitized solar cells. The cells show IPCE values of greater than 90%, PCEs of up to 7.12%, and high open circuit voltages reaching close to 0.8 V based on the iodide/triiodide electrolyte.

  我们证明了一种碳桥接苯乙烯（CPV）连接染料可作为染料敏化太阳能电池的新型高效敏化剂。这种电池的 IPCE 值超过 90%，PCE 值高达 7.12%，基于碘/三碘化物电解质的开路电压高达 0.8 V。