5-(5'-{5-[4-(diphenylamino)phenyl]thiophen-2-yl}-4,4'-dihexyl-2,2'-bithiazol-5-yl)furan-2-carbaldehyde | 1392316-07-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-(5'-{5-[4-(diphenylamino)phenyl]thiophen-2-yl}-4,4'-dihexyl-2,2'-bithiazol-5-yl)furan-2-carbaldehyde
• CAS: 1392316-07-2
• 化学式: C₄₅H₄₅N₃O₂S₃
• 分子量: 756.069
• InChiKey: GOACPUGIYPJTDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.45
• 重原子数：
  53.0
• 可旋转键数：
  18.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  59.23
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5-(5'-{5-[4-(diphenylamino)phenyl]thiophen-2-yl}-4,4'-dihexyl-2,2'-bithiazol-5-yl)furan-2-carbaldehyde 、 氰乙酸 在 ammonium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 以87%的产率得到2-cyano-3-[5-(5'-{5-[4-(diphenylamino)phenyl]thiophen-2-yl}-4,4'-dihexyl-2,2'-bithiazol-5-yl)furan-2-yl]acrylic acid
  参考文献：
  名称：

  New Bithiazole-Based Sensitizers for Efficient and Stable Dye-Sensitized Solar Cells

  摘要：

  AbstractA series of new push–pull organic dyes (BT‐I–VI), incorporating electron‐withdrawing bithiazole with a thiophene, furan, benzene, or cyano moiety, as π spacer have been synthesized, characterized, and used as the sensitizers for dye‐sensitized solar cells (DSSCs). In comparison with the model compound T1, these dyes containing a thiophene moiety between triphenylamine and bithiazole display enhanced spectral responses in the red portion of the solar spectrum. Electrochemical measurement data indicate that the HOMO and LUMO energy levels can be tuned by introducing different π spacers between the bithiazole moiety and cyanoacrylic acid acceptor. The incorporation of bithiazole substituted with two hexyl groups is highly beneficial to prevent close π–π aggregation, thus favorably suppressing charge recombination and intermolecular interaction. The overall conversion efficiencies of DSSCs based on bithiazole dyes are in the range of 3.58 to 7.51 %, in which BT‐I‐based DSSCs showed the best photovoltaic performance: a maximum monochromatic incident photon‐to‐current conversion efficiency (IPCE) of 81.1 %, a short‐circuit photocurrent density (Jsc) of 15.69 mA cm−2, an open‐circuit photovoltage (Voc) of 778 mV, and a fill factor (ff) of 0.61, which correspond to an overall conversion efficiency of 7.51 % under standard global AM 1.5 solar light conditions. Most importantly, long‐term stability of the BT‐I–III‐based DSSCs with ionic‐liquid electrolytes under 1000 h of light soaking was demonstrated and BT‐II with a furan moiety exhibited better photovoltaic performance of up to 5.75 % power conversion efficiency.

  DOI：

  10.1002/chem.201103702
• 作为产物：
  描述：

  5-bromo-4,4'-dihexyl-5'-(thiophen-2-yl)-2,2'-bithiazole 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 氯仿 、 水 为溶剂， 反应 8.0h， 生成 5-(5'-{5-[4-(diphenylamino)phenyl]thiophen-2-yl}-4,4'-dihexyl-2,2'-bithiazol-5-yl)furan-2-carbaldehyde
  参考文献：
  名称：

  New Bithiazole-Based Sensitizers for Efficient and Stable Dye-Sensitized Solar Cells

  摘要：

  AbstractA series of new push–pull organic dyes (BT‐I–VI), incorporating electron‐withdrawing bithiazole with a thiophene, furan, benzene, or cyano moiety, as π spacer have been synthesized, characterized, and used as the sensitizers for dye‐sensitized solar cells (DSSCs). In comparison with the model compound T1, these dyes containing a thiophene moiety between triphenylamine and bithiazole display enhanced spectral responses in the red portion of the solar spectrum. Electrochemical measurement data indicate that the HOMO and LUMO energy levels can be tuned by introducing different π spacers between the bithiazole moiety and cyanoacrylic acid acceptor. The incorporation of bithiazole substituted with two hexyl groups is highly beneficial to prevent close π–π aggregation, thus favorably suppressing charge recombination and intermolecular interaction. The overall conversion efficiencies of DSSCs based on bithiazole dyes are in the range of 3.58 to 7.51 %, in which BT‐I‐based DSSCs showed the best photovoltaic performance: a maximum monochromatic incident photon‐to‐current conversion efficiency (IPCE) of 81.1 %, a short‐circuit photocurrent density (Jsc) of 15.69 mA cm−2, an open‐circuit photovoltage (Voc) of 778 mV, and a fill factor (ff) of 0.61, which correspond to an overall conversion efficiency of 7.51 % under standard global AM 1.5 solar light conditions. Most importantly, long‐term stability of the BT‐I–III‐based DSSCs with ionic‐liquid electrolytes under 1000 h of light soaking was demonstrated and BT‐II with a furan moiety exhibited better photovoltaic performance of up to 5.75 % power conversion efficiency.

  DOI：

  10.1002/chem.201103702