2-(2,3-di(5-octylthiophen-2-yl)thiophen-5-yl)-1H-imidazo[4,5-f][1,10]phenanthroline | 1239368-62-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 2-(2,3-di(5-octylthiophen-2-yl)thiophen-5-yl)-1H-imidazo[4,5-f][1,10]phenanthroline
• 英文别名: 2-[4,5-bis(5-octylthiophen-2-yl)thiophen-2-yl]-1H-imidazo[4,5-f][1,10]phenanthroline
• CAS: 1239368-62-7
• 化学式: C₄₁H₄₆N₄S₃
• 分子量: 691.041
• InChiKey: HVXCEQNTIGWVQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.9
• 重原子数：
  48
• 可旋转键数：
  17
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  三甲基锡烷(5-辛基-2-噻吩基)- 在 bis-triphenylphosphine-palladium(II) chloride 、 正丁基锂 、 ammonium acetate 作用下， 以 四氢呋喃 、 正己烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 2-(2,3-di(5-octylthiophen-2-yl)thiophen-5-yl)-1H-imidazo[4,5-f][1,10]phenanthroline
  参考文献：
  名称：

  Toward Optimization of Oligothiophene Antennas: New Ruthenium Sensitizers with Excellent Performance for Dye-Sensitized Solar Cells

  摘要：

  This paper reports on the design and synthesis of three new ruthenium sensitizers, as well as the optimization of their linear or dendritic light-harvesting oligothiophene antennas to achieve superior device performance. The three new ruthenium sensitizers, [Ru(dcbpy)(obtip)(NCS)(2)] (JF-5, dcbpy = 4,4'-dicarboxylic obtip = 2-(5-octyl-(2,2'-bithiophen)-5'-yl)-1H-imidazo[4,51][1,10]-phenanthroline), [Ru(dcbpy)(ottip)(NCS)(2)] (JF-6, ottip = 2-(5-octyl-2,2',5',2 ''-terthiophen)-5 ''-yl)-1H-imidazo[4,5-f][1,10]-phenanthroline), and [Ru(dcbpy)(dottip)(NCS)(2)] (JF-7, dottip = di-(5-octylthiophen-2-ypthiophen-5-yl)-1H-imidazo[4,5-f][1,10]phenanthroline), were synthesized in a typical one-pot reaction. The ruthenium sensitizer JF-5 incorporating a linear and planar 2,2'-bithiophene antenna showed the best DSCs performance (9.5%; compared to N3, 8.8%). The difference in the performance of these sensitizers demonstrates that elongating the linear and planar light-harvesting antenna result in an enhancement in MLCT intensity, but a reduction in the quantity of dye-loading. This finding not only permitted the power-conversion efficiency in ruthenium sensitizers containing oligothiophene antennas to be optimized, but also points to a promising direction for molecule engineering in DSCs.

  DOI：

  10.1021/cm100770x

文献信息

• Toward Optimization of Oligothiophene Antennas: New Ruthenium Sensitizers with Excellent Performance for Dye-Sensitized Solar Cells
  作者：Jen-Fu Yin、Jian-Ging Chen、Zong-Zhan Lu、Kuo-Chuan Ho、Hong-Cheu Lin、Kuang-Lieh Lu

  DOI：10.1021/cm100770x

  日期：2010.8.10

  This paper reports on the design and synthesis of three new ruthenium sensitizers, as well as the optimization of their linear or dendritic light-harvesting oligothiophene antennas to achieve superior device performance. The three new ruthenium sensitizers, [Ru(dcbpy)(obtip)(NCS)(2)] (JF-5, dcbpy = 4,4'-dicarboxylic obtip = 2-(5-octyl-(2,2'-bithiophen)-5'-yl)-1H-imidazo[4,51][1,10]-phenanthroline), [Ru(dcbpy)(ottip)(NCS)(2)] (JF-6, ottip = 2-(5-octyl-2,2',5',2 ''-terthiophen)-5 ''-yl)-1H-imidazo[4,5-f][1,10]-phenanthroline), and [Ru(dcbpy)(dottip)(NCS)(2)] (JF-7, dottip = di-(5-octylthiophen-2-ypthiophen-5-yl)-1H-imidazo[4,5-f][1,10]phenanthroline), were synthesized in a typical one-pot reaction. The ruthenium sensitizer JF-5 incorporating a linear and planar 2,2'-bithiophene antenna showed the best DSCs performance (9.5%; compared to N3, 8.8%). The difference in the performance of these sensitizers demonstrates that elongating the linear and planar light-harvesting antenna result in an enhancement in MLCT intensity, but a reduction in the quantity of dye-loading. This finding not only permitted the power-conversion efficiency in ruthenium sensitizers containing oligothiophene antennas to be optimized, but also points to a promising direction for molecule engineering in DSCs.