bis[4-(5-formyl-2-thienyl)phenyl]-{4-[5-(2-thienylethen-2-yl)-2-thienyl]phenyl}amine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: bis[4-(5-formyl-2-thienyl)phenyl]-{4-[5-(2-thienylethen-2-yl)-2-thienyl]phenyl}amine
• 英文别名: 5-[4-[N-[4-(5-formylthiophen-2-yl)phenyl]-4-[5-[(E)-2-thiophen-2-ylethenyl]thiophen-2-yl]anilino]phenyl]thiophene-2-carbaldehyde
• 化学式: C₃₈H₂₅NO₂S₄
• 分子量: 655.886
• InChiKey: VNNZSVOFKLGYGL-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  45
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  bis[4-(5-formyl-2-thienyl)phenyl]-{4-[5-(2-thienylethen-2-yl)-2-thienyl]phenyl}amine 、 丙二腈 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 15.0h， 以48%的产率得到bis[4-(5-dicyanomethylidenemethyl-2-thienyl)phenyl]-{4-[5-(2-thienylethen-2-yl)-2-thienyl]phenyl}amine
  参考文献：
  名称：

  Triphenylamine−Thienylenevinylene Hybrid Systems with Internal Charge Transfer as Donor Materials for Heterojunction Solar Cells

  摘要：

  Star-shaped molecules based on a triphenylamine core derivatized with various combinations of thienylenevinylene conjugated branches and electron-withdrawing indanedione or dicyanovinyl groups have been synthesized. UV-vis absorption and fluorescence emission data show that the introduction of the electron-acceptor groups induces an intramolecular charge transfer that results in a shift of the absorption onset toward longer wavelengths and a quenching of photoluminescence. Cyclic voltammetry shows that all compounds present a reversible first oxidation process whose potential increases with the number of electron-withdrawing groups in the structure. Prototype bulk and bilayer heterojunction solar cells have been realized using fullerene C-60 derivatives as acceptor material. The results obtained with both kinds of devices show that the introduction of electron-acceptor groups in the donor structure induces an extension of the photoresponse in the visible spectral region, an increase of the maximum external quantum efficiency, and an increase of the open-circuit voltage under white light illumination. These synergistic effects allow reaching power conversion efficiencies of similar to 1.20% under simulated AM 1.5 solar irradiation at 100 mW cm(-2).

  DOI：

  10.1021/ja058178e
• 作为产物：
  描述：

  三(4-溴苯基)胺 在 四(三苯基膦)钯 、 potassium tert-butylate 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 30.0h， 生成 bis[4-(5-formyl-2-thienyl)phenyl]-{4-[5-(2-thienylethen-2-yl)-2-thienyl]phenyl}amine
  参考文献：
  名称：

  Triphenylamine−Thienylenevinylene Hybrid Systems with Internal Charge Transfer as Donor Materials for Heterojunction Solar Cells

  摘要：

  Star-shaped molecules based on a triphenylamine core derivatized with various combinations of thienylenevinylene conjugated branches and electron-withdrawing indanedione or dicyanovinyl groups have been synthesized. UV-vis absorption and fluorescence emission data show that the introduction of the electron-acceptor groups induces an intramolecular charge transfer that results in a shift of the absorption onset toward longer wavelengths and a quenching of photoluminescence. Cyclic voltammetry shows that all compounds present a reversible first oxidation process whose potential increases with the number of electron-withdrawing groups in the structure. Prototype bulk and bilayer heterojunction solar cells have been realized using fullerene C-60 derivatives as acceptor material. The results obtained with both kinds of devices show that the introduction of electron-acceptor groups in the donor structure induces an extension of the photoresponse in the visible spectral region, an increase of the maximum external quantum efficiency, and an increase of the open-circuit voltage under white light illumination. These synergistic effects allow reaching power conversion efficiencies of similar to 1.20% under simulated AM 1.5 solar irradiation at 100 mW cm(-2).

  DOI：

  10.1021/ja058178e

文献信息

• Triphenylamine−Thienylenevinylene Hybrid Systems with Internal Charge Transfer as Donor Materials for Heterojunction Solar Cells
  作者：Sophie Roquet、Antonio Cravino、Philippe Leriche、Olivier Alévêque、Pierre Frère、Jean Roncali

  DOI：10.1021/ja058178e

  日期：2006.3.1

  Star-shaped molecules based on a triphenylamine core derivatized with various combinations of thienylenevinylene conjugated branches and electron-withdrawing indanedione or dicyanovinyl groups have been synthesized. UV-vis absorption and fluorescence emission data show that the introduction of the electron-acceptor groups induces an intramolecular charge transfer that results in a shift of the absorption onset toward longer wavelengths and a quenching of photoluminescence. Cyclic voltammetry shows that all compounds present a reversible first oxidation process whose potential increases with the number of electron-withdrawing groups in the structure. Prototype bulk and bilayer heterojunction solar cells have been realized using fullerene C-60 derivatives as acceptor material. The results obtained with both kinds of devices show that the introduction of electron-acceptor groups in the donor structure induces an extension of the photoresponse in the visible spectral region, an increase of the maximum external quantum efficiency, and an increase of the open-circuit voltage under white light illumination. These synergistic effects allow reaching power conversion efficiencies of similar to 1.20% under simulated AM 1.5 solar irradiation at 100 mW cm(-2).