2,2'''-bis(1-ethynyl-4-(2,2'-dibromo-4-ethynyl-heptafluororbiphenyl)-tetrafluorophenyl)-4,4000-dihexyl-5,2',2'',5''',5',5''-quaterthiophene | 1219681-04-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2'''-bis(1-ethynyl-4-(2,2'-dibromo-4-ethynyl-heptafluororbiphenyl)-tetrafluorophenyl)-4,4000-dihexyl-5,2',2'',5''',5',5''-quaterthiophene
• 英文别名: Br2-ADA；5-[2-[4-[2-[3-Bromo-4-(2-bromo-3,4,5,6-tetrafluorophenyl)-2,5,6-trifluorophenyl]ethynyl]-2,3,5,6-tetrafluorophenyl]ethynyl]-2-[5-[5-[5-[2-[4-[2-[3-bromo-4-(2-bromo-3,4,5,6-tetrafluorophenyl)-2,5,6-trifluorophenyl]ethynyl]-2,3,5,6-tetrafluorophenyl]ethynyl]-3-hexylthiophen-2-yl]thiophen-2-yl]thiophen-2-yl]-3-hexylthiophene
• CAS: 1219681-04-5
• 化学式: C₇₂H₃₂Br₄F₂₂S₄
• 分子量: 1762.89
• InChiKey: YJFWVJDPTSKGON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  28
• 重原子数：
  102
• 可旋转键数：
  23
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  26

反应信息

• 作为产物：
  描述：

  2,2'-dibromo-4-ethynyl-3,3',4',5,5',6,6'-heptafluorobiphenyl 、 2,2'''-bis(1-ethynyl-4-iodo-tetrafluorophenyl)-4,4'''-dihexyl-5,2',2'',5''',5',5''-quaterthiophene 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67%的产率得到2,2'''-bis(1-ethynyl-4-(2,2'-dibromo-4-ethynyl-heptafluororbiphenyl)-tetrafluorophenyl)-4,4000-dihexyl-5,2',2'',5''',5',5''-quaterthiophene
  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

文献信息

• Synthesis and Characterization of Fluorinated Heterofluorene-Containing Donor−Acceptor Systems
  作者：Katharine Geramita、Yuefei Tao、Rachel A. Segalman、T. Don Tilley

  DOI：10.1021/jo902488w

  日期：2010.3.19

  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.