5-[5-(5-Formylthiophen-2-yl)-3-[[4-[2-[4-[2-[4-[4-(5-formylthiophen-2-yl)-2-[2-(5-formylthiophen-2-yl)ethynyl]but-1-en-3-ynyl]phenyl]ethynyl]-2,5-dihexoxyphenyl]ethynyl]phenyl]methylidene]penta-1,4-diynyl]thiophene-2-carbaldehyde | 1022991-37-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-[5-(5-Formylthiophen-2-yl)-3-[[4-[2-[4-[2-[4-[4-(5-formylthiophen-2-yl)-2-[2-(5-formylthiophen-2-yl)ethynyl]but-1-en-3-ynyl]phenyl]ethynyl]-2,5-dihexoxyphenyl]ethynyl]phenyl]methylidene]penta-1,4-diynyl]thiophene-2-carbaldehyde
• 英文别名: 5-[5-(5-formylthiophen-2-yl)-3-[[4-[2-[4-[2-[4-[4-(5-formylthiophen-2-yl)-2-[2-(5-formylthiophen-2-yl)ethynyl]but-1-en-3-ynyl]phenyl]ethynyl]-2,5-dihexoxyphenyl]ethynyl]phenyl]methylidene]penta-1,4-diynyl]thiophene-2-carbaldehyde
• CAS: 1022991-37-2
• 化学式: C₆₆H₅₀O₆S₄
• 分子量: 1067.38
• InChiKey: XXMSDDXVBOWQFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.8
• 重原子数：
  76
• 可旋转键数：
  30
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  173
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  5-溴噻吩-2-甲醛 、 [3-[[4-[2-[2,5-Dihexoxy-4-[2-[4-[4-trimethylsilyl-2-(2-trimethylsilylethynyl)but-1-en-3-ynyl]phenyl]ethynyl]phenyl]ethynyl]phenyl]methylidene]-5-trimethylsilylpenta-1,4-diynyl]-trimethylsilane 在 bis-triphenylphosphine-palladium(II) chloride potassium fluoride 、 copper(l) iodide 、 三乙胺 作用下， 以 甲醇 为溶剂， 以32%的产率得到5-[5-(5-Formylthiophen-2-yl)-3-[[4-[2-[4-[2-[4-[4-(5-formylthiophen-2-yl)-2-[2-(5-formylthiophen-2-yl)ethynyl]but-1-en-3-ynyl]phenyl]ethynyl]-2,5-dihexoxyphenyl]ethynyl]phenyl]methylidene]penta-1,4-diynyl]thiophene-2-carbaldehyde
  参考文献：
  名称：

  Tetrafullerene Conjugates for All-Organic Photovoltaics

  摘要：

  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.

  DOI：

  10.1021/jo702740d

文献信息

• 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.