3,10-diiodo-5,7,12,14-tetrahydro-5,5,12,12-tetra(p-octylphenyl)-7,7,14,14-tetraphenyl-di(indeno[2,1-a:2’,1’-d’])-s-indacene | 1334701-44-8

• 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: 3,10-diiodo-5,7,12,14-tetrahydro-5,5,12,12-tetra(p-octylphenyl)-7,7,14,14-tetraphenyl-di(indeno[2,1-a:2’,1’-d’])-s-indacene
• 英文别名: 3,10-diiodo-5,7,12,14-tetrahydro-5,5,12,12-tetra(p-octylphenyl)-7,7,14,14-tetraphenyl-di(indeno[2,1-a:2',1'-d'])-s-indacene；8,21-Diiodo-5,5,18,18-tetrakis(4-octylphenyl)-13,13,26,26-tetraphenylheptacyclo[14.10.0.03,14.04,12.06,11.017,25.019,24]hexacosa-1(16),2,4(12),6(11),7,9,14,17(25),19(24),20,22-undecaene
• CAS: 1334701-44-8
• 化学式: C₁₀₆H₁₁₂I₂
• 分子量: 1639.86
• InChiKey: XAGOCEQHGKTCEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  34.9
• 重原子数：
  108
• 可旋转键数：
  36
• 环数：
  15.0
• sp3杂化的碳原子比例：
  0.34
• 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：

  3,10-diiodo-5,7,12,14-tetrahydro-5,5,12,12-tetra(p-octylphenyl)-7,7,14,14-tetraphenyl-di(indeno[2,1-a:2’,1’-d’])-s-indacene 、 丙二腈 在 sodium hydride 、 四(三苯基膦)钯 、 三苯基膦 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 8.17h， 以60%的产率得到3,11-bis(dicyanomethylene)-3,11-dyhydro-Δ5,7,12,14-tetrahydro-5,5,12,12-tetra(p-octylphenyl)-7,7,14,14-tetraphenyl-di(indeno[2,1-a:2',1'-d'])-s-indacene
  参考文献：
  名称：

  Air- and Heat-Stable Planar Tri-p-quinodimethane with Distinct Biradical Characteristics

  摘要：

  A heptacyclic carbocycle possessing three p-quinodimethane units conjugated in one plane has been synthesized and shown to exhibit distinct biradical characteristics. The molecule has a HOMO/LUMO band gap of ca. 1 eV and a S(0)-T(1) energy gap of 2.12 kcal/mol, and it absorbs and emits near-IR light at room temperature. It is air-stable under ambient light for several months and thermally stable up to 160 degrees C under nitrogen, and it undergoes reversible two-electron oxidation and reduction. The synthetic approach is such that a smaller and larger oligo-p-quinodimethane can be synthesized.

  DOI：

  10.1021/ja206060n
• 作为产物：
  描述：

  3,10-dibromo-5,7,12,14-tetrahydro-5,5,12,12-tetra(p-octylphenyl)-7,7,14,14-tetraphenyl-di(indeno[2,1-a:2’,1’-d’])-s-indacene 在 正丁基锂 、 1,2-二碘乙烷 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.5h， 以97%的产率得到3,10-diiodo-5,7,12,14-tetrahydro-5,5,12,12-tetra(p-octylphenyl)-7,7,14,14-tetraphenyl-di(indeno[2,1-a:2’,1’-d’])-s-indacene
  参考文献：
  名称：

  Air- and Heat-Stable Planar Tri-p-quinodimethane with Distinct Biradical Characteristics

  摘要：

  A heptacyclic carbocycle possessing three p-quinodimethane units conjugated in one plane has been synthesized and shown to exhibit distinct biradical characteristics. The molecule has a HOMO/LUMO band gap of ca. 1 eV and a S(0)-T(1) energy gap of 2.12 kcal/mol, and it absorbs and emits near-IR light at room temperature. It is air-stable under ambient light for several months and thermally stable up to 160 degrees C under nitrogen, and it undergoes reversible two-electron oxidation and reduction. The synthetic approach is such that a smaller and larger oligo-p-quinodimethane can be synthesized.

  DOI：

  10.1021/ja206060n

文献信息

• Carbon-Bridged Oligo(phenylenevinylene)s: Stable π-Systems with High Responsiveness to Doping and Excitation
  作者：Xiaozhang Zhu、Hayato Tsuji、Juan T. López Navarrete、Juan Casado、Eiichi Nakamura

  DOI：10.1021/ja309318s

  日期：2012.11.21

  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.