5-(1-ethynyl-4-iodo-tetrafluorophenyl)-5'-hexyl-2,2'-bithiophene | 1219681-00-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5-(1-ethynyl-4-iodo-tetrafluorophenyl)-5'-hexyl-2,2'-bithiophene
• 英文别名: 2-Hexyl-5-[5-[2-(2,3,5,6-tetrafluoro-4-iodophenyl)ethynyl]thiophen-2-yl]thiophene
• CAS: 1219681-00-1
• 化学式: C₂₂H₁₇F₄IS₂
• 分子量: 548.407
• InChiKey: QZOGYEFETYMPHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4'-bisethynyl-2,2'-dibromo-3,3',5,5',6,6'-hexafluorobiphenyl 、 5-(1-ethynyl-4-iodo-tetrafluorophenyl)-5'-hexyl-2,2'-bithiophene 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 、 三苯基膦 作用下， 反应 12.0h， 以90%的产率得到2,2'-dibromo-4,4'-bis(1-(5-ethynyl-5'-hexyl-2,2'-bithienyl)-4-ethynyltetrafluorophenyl)-hexafluorobiphenyl
  参考文献：
  名称：

  Synthesis and Characterization of Fluorinated Heterofluorene-Containing Donor−Acceptor Systems

  摘要：

  A series of oligothiopheiie-perfluoro-9-heterofluorene donor-acceptor (DA) compounds was synthesized via a combination of nucleophilic aromatic substitution (SNArF) and palladium coupling reactions. These compounds are of interest as possible building blocks for materials with useful electron transport properties, since they possess relatively low LUMO energy levels of -3.3 to -3.6 eV (as determined by differential Pulse voltammetry), The HOMO-LUMO energy gaps, as determined by UV-vis spectroscopy, range between 2.4 and 2.5 eV, and photoluminescence emission spectra reveal lambda(ems) values in the range of 480-600 nm (corresponding to yellow-orange emission). Dilute solution-state photolummescence quantum yields were significantly lower than those of the pure acceptor heterofluorenes (0.02-0.38 for the DA compounds vs similar to 1 for the pure acceptors), and notable solvatochromisin in the fluorescence suggests emission from a charge-separated state. Theoretical calculations show that HOMO-level electron density is more localized on the thiophene fragment, while the LUMO level electron density is mostly associated with the electron-deficient portion of the molecule. Photovoltaic (PV) devices based on DA/poly-3-hexylthiophene (P3HT) blends exhibit improved performance over P3HT-only devices, suggesting the ability of these DA compounds to transport electrons in the solid state.

  DOI：

  10.1021/jo902488w
• 作为产物：
  描述：

  5-(1-ethynyl-4-bromo-tetrafluorophenyl)-5'-hexyl-2,2'-bithiophene 在 正丁基锂 、 碘 作用下， 以 乙醚 、 正己烷 、 甲苯 、 甲醚 为溶剂， 反应 0.33h， 以98%的产率得到5-(1-ethynyl-4-iodo-tetrafluorophenyl)-5'-hexyl-2,2'-bithiophene
  参考文献：
  名称：

  Synthesis and Characterization of Fluorinated Heterofluorene-Containing Donor−Acceptor Systems

  摘要：

  A series of oligothiopheiie-perfluoro-9-heterofluorene donor-acceptor (DA) compounds was synthesized via a combination of nucleophilic aromatic substitution (SNArF) and palladium coupling reactions. These compounds are of interest as possible building blocks for materials with useful electron transport properties, since they possess relatively low LUMO energy levels of -3.3 to -3.6 eV (as determined by differential Pulse voltammetry), The HOMO-LUMO energy gaps, as determined by UV-vis spectroscopy, range between 2.4 and 2.5 eV, and photoluminescence emission spectra reveal lambda(ems) values in the range of 480-600 nm (corresponding to yellow-orange emission). Dilute solution-state photolummescence quantum yields were significantly lower than those of the pure acceptor heterofluorenes (0.02-0.38 for the DA compounds vs similar to 1 for the pure acceptors), and notable solvatochromisin in the fluorescence suggests emission from a charge-separated state. Theoretical calculations show that HOMO-level electron density is more localized on the thiophene fragment, while the LUMO level electron density is mostly associated with the electron-deficient portion of the molecule. Photovoltaic (PV) devices based on DA/poly-3-hexylthiophene (P3HT) blends exhibit improved performance over P3HT-only devices, suggesting the ability of these DA compounds to transport electrons in the solid state.

  DOI：

  10.1021/jo902488w