4-[2-[4-[2-(4-Formylphenyl)ethynyl]-2,5-dihexoxyphenyl]ethynyl]benzaldehyde | 830336-63-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-[2-[4-[2-(4-Formylphenyl)ethynyl]-2,5-dihexoxyphenyl]ethynyl]benzaldehyde
• 英文别名: 4-[2-[4-[2-(4-formylphenyl)ethynyl]-2,5-dihexoxyphenyl]ethynyl]benzaldehyde
• CAS: 830336-63-5
• 化学式: C₃₆H₃₈O₄
• 分子量: 534.695
• InChiKey: HLQXLCHSFVJFKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  40
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1,4-二(己氧基)-2,5-二碘苯 在 哌啶 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 4-[2-[4-[2-(4-Formylphenyl)ethynyl]-2,5-dihexoxyphenyl]ethynyl]benzaldehyde
  参考文献：
  名称：

  Connecting two C₆₀stoppers to molecular wires: ultrafast intramolecular deactivation reactions

  摘要：

  我们采用聚合合成策略制备了一系列新的可溶性哑铃型结构，这些结构由 π 共轭的低聚苯乙炔（OPE）和两个 C60 阻聚剂构成。特别是，我们的方法基于芳基碘化物和炔基衍生物之间的系统交叉耦合、钯催化萩原-索诺伽希拉（Hagihara-Sonogashira）反应。相应合成体系的循环伏安法显示了两性氧化还原行为，低聚芳基炔桥和两个 C60 分子之间缺乏明显的电子通信，它们表现为两个独立的单元。通过荧光和过渡吸收光谱进行的激发态研究表明，虽然在激发的低聚芳基炔桥的失活过程中可能存在微弱的竞争性电子转移，但它们的失活主要受能量转移的支配。

  DOI：

  10.1039/b412110d

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%。
• Connecting two C₆₀stoppers to molecular wires: ultrafast intramolecular deactivation reactions
  作者：Carmen Atienza、Braulio Insuasty、Carlos Seoane、Nazario Martín、Jeff Ramey、G. M. Aminur Rahman、Dirk M. Guldi

  DOI：10.1039/b412110d

  日期：——

  A new series of soluble dumbbell-type architectures constituted by π-conjugated oligophenyleneethynylenes (OPEs) and two C60 stoppers have been prepared by using a convergent synthetic strategy. In particular, we base our approach on the systematic cross-coupling, palladium catalyzed Hagihara–Sonogashira reaction between aryl iodides and alkynyl derivatives. The cyclic voltammetry of the correspondingly synthesized system reveals amphoteric redox behavior and the lack of significant electronic communication between the oligo-arylalkynyl bridge and the two C60 moieties, which behave as two independent units. Excited state studies carried out by fluorescence and transition absorption spectroscopy show that, although a weak competitive electron transfer could operate in the deactivation process of the excited oligo-arylalkynyl bridges, their deactivation is mainly governed by energy transfer.

  我们采用聚合合成策略制备了一系列新的可溶性哑铃型结构，这些结构由 π 共轭的低聚苯乙炔（OPE）和两个 C60 阻聚剂构成。特别是，我们的方法基于芳基碘化物和炔基衍生物之间的系统交叉耦合、钯催化萩原-索诺伽希拉（Hagihara-Sonogashira）反应。相应合成体系的循环伏安法显示了两性氧化还原行为，低聚芳基炔桥和两个 C60 分子之间缺乏明显的电子通信，它们表现为两个独立的单元。通过荧光和过渡吸收光谱进行的激发态研究表明，虽然在激发的低聚芳基炔桥的失活过程中可能存在微弱的竞争性电子转移，但它们的失活主要受能量转移的支配。
• 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.