1,4-bis(2-(4-(2,2-dibromovinyl)phenyl)ethynyl)-2,5-dihexyloxybenzene | 880486-73-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,4-bis(2-(4-(2,2-dibromovinyl)phenyl)ethynyl)-2,5-dihexyloxybenzene
• 英文别名: 1,4-Bis[2-[4-(2,2-dibromoethenyl)phenyl]ethynyl]-2,5-dihexoxybenzene；1,4-bis[2-[4-(2,2-dibromoethenyl)phenyl]ethynyl]-2,5-dihexoxybenzene
• CAS: 880486-73-7
• 化学式: C₃₈H₃₈Br₄O₂
• 分子量: 846.335
• InChiKey: UZUPSTBZAVSHLX-UHFFFAOYSA-N

物化性质

• 沸点：
  786.3±60.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.6
• 重原子数：
  44
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-bis(2-(4-(2,2-dibromovinyl)phenyl)ethynyl)-2,5-dihexyloxybenzene 、 4-乙炔基苯甲醛 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 作用下， 以 甲醇 、 三乙胺 为溶剂， 反应 5.0h， 以72%的产率得到1,4-bis[[1,4-bis[4-(4-formylphenyl)-2-(4-formylphenyl)ethynyl]but-1-en-3-ynyl]-(phenyl)ethynyl]-2,5-dihexyloxybenzene
  参考文献：
  名称：

  Light harvesting tetrafullerene nanoarray for organic solar cells

  摘要：

  我们合成了一种可吸收光的π-共轭低聚物-四烯烃纳米阵列，对其进行的光物理研究揭示了分子内能量转移的存在。用这种纳米阵列和聚（3-己基噻吩）制造的光伏装置在 500 纳米波长下的外部量子效率为 15%。

  DOI：

  10.1039/b510234k
• 作为产物：
  描述：

  四溴化碳 、 4-[2-[4-[2-(4-Formylphenyl)ethynyl]-2,5-dihexoxyphenyl]ethynyl]benzaldehyde 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以97%的产率得到1,4-bis(2-(4-(2,2-dibromovinyl)phenyl)ethynyl)-2,5-dihexyloxybenzene
  参考文献：
  名称：

  Light harvesting tetrafullerene nanoarray for organic solar cells

  摘要：

  我们合成了一种可吸收光的π-共轭低聚物-四烯烃纳米阵列，对其进行的光物理研究揭示了分子内能量转移的存在。用这种纳米阵列和聚（3-己基噻吩）制造的光伏装置在 500 纳米波长下的外部量子效率为 15%。

  DOI：

  10.1039/b510234k

文献信息

• Light harvesting tetrafullerene nanoarray for organic solar cells
  作者：Carmen M. Atienza、Gustavo Fernández、Luis Sánchez、Nazario Martín、Inês Sá Dantas、Martijn M. Wienk、René A. J. Janssen、G. M. Aminur Rahman、Dirk M. Guldi

  DOI：10.1039/b510234k

  日期：——

  A light absorbing π-conjugated oligomer–tetrafullerene nanoarray has been synthesized and its photophysical study reveals the presence of an intramolecular energy transfer. A phototovoltaic device fabricated from this nanoarray and poly(3-hexylthiophene) shows an external quantum efficiency of 15% at 500 nm.

  我们合成了一种可吸收光的π-共轭低聚物-四烯烃纳米阵列，对其进行的光物理研究揭示了分子内能量转移的存在。用这种纳米阵列和聚（3-己基噻吩）制造的光伏装置在 500 纳米波长下的外部量子效率为 15%。
• Tetrafullerene Conjugates for All-Organic Photovoltaics
  作者：Gustavo Fernández、Luis Sánchez、Dirk Veldman、Martijn M. Wienk、Carmen Atienza、Dirk M. Guldi、René A. J. Janssen、Nazario Martín

  DOI：10.1021/jo702740d

  日期：2008.4.1

  The synthesis of two new tetrafullerene nanoconjugates in which four C-60 units are covalently connected through different pi-conjugated oligomers (oligo(p-phenylene ethynylene) and oligo(p-phenylene vinylene)) is described. The photovoltaic (PV) response of these C-60-based conjugates was evaluated by using them as the only active material in organic solar cells, showing a low PV performance. Photophysical studies in solution demonstrated a very fast (similar to 10 ps) deactivation of the singlet excited state of the central core unit to produce both charge-separated species (i.e., C-60(center dot-)-oligomer(+center dot)-(C-60)(3) and C-60 centered singlet excited states). The charge-separated state recombines partly to the C-60 centered singlet state that undergoes subsequent intersystem crossing. Photophysical studies carried out in films support these data, exhibiting long-lived triplet excited states. For both tetrafullerene arrays, the low yield of long-lived charge carriers in thin films accounts for the limited PV response. On the contrary, utilizing the oligo(p-phenylene vinylene) centered precursor aldehyde as an electron donor and antennae unit and mixing with the well-known C-60 derivative PCBM, the photophysical studies in films show the formation of long-lived charges. The PV devices constructed from these mixtures showed a relatively high photocurrent of 2 mA cm(-2). The sharp contrast between the nanoconjugates and the physical blends tentatively was attributed to improved charge dissociation and the collection of more favorable energy levels in the blends as a result of partial aggregation of both of the components.