1,2,4,6,8,9-Hexafluoro-3,7-bis(2-phenylethynyl)dibenzothiophene | 1095101-46-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 1,2,4,6,8,9-Hexafluoro-3,7-bis(2-phenylethynyl)dibenzothiophene
• CAS: 1095101-46-4
• 化学式: C₂₈H₁₀F₆S
• 分子量: 492.444
• InChiKey: XQWJIWQDESPGDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,2'-dibromo-4,4'-bis(phenylethynyl)-3,3',5,5',6,6'-hexafluorobiphenyl 在 正丁基锂 、 二氯化二硫 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 10.0h， 以40%的产率得到1,2,4,6,8,9-Hexafluoro-3,7-bis(2-phenylethynyl)dibenzothiophene
  参考文献：
  名称：

  2,7-Substituted Hexafluoroheterofluorenes as Potential Building Blocks for Electron Transporting Materials

  摘要：

  A series of 2,7-substituted hexafluoro-9-heterofluorenes was synthesized via nucleophilic aromatic substitution (SNArF) reactions of phenyllithium, thienyllithium, and lithium phenylacetylide with various octafluoroheterofluorenes and 2,2'-dibromooctafluorobiphenyl. These compounds are of interest as possible building blocks for materials with useful electron transport properties, since they possess relatively low LUMO energy levels. The HOMO-LUMO energy gaps, as determined by UV-vis spectroscopy, range between 3.0 and 3.9 eV, while photoluminescence emission spectra reveal lambda(ems) values in the range of 365 to 420 nm (corresponding to ultraviolet to violet/blue emission). Dilute solution state quantum yields vary significantly with the nature of the heteroatom and the 2,7-substituents, and approach unity for a number of the di(phenylethynyl) derivatives. The experimentally determined LUMO energy levels (-2.7 to -3.3 eV as determined by differential pulse voltammetry) suggest that these compounds may be good candidates for electron transport applications. Single-crystal X-ray analyses of a number of compounds revealed cofacial packing in all cases, with intermolecular distances as short as 3.4 angstrom.

  DOI：

  10.1021/jo802171t

文献信息

• 2,7-Substituted Hexafluoroheterofluorenes as Potential Building Blocks for Electron Transporting Materials
  作者：Katharine Geramita、Jennifer McBee、T. Don Tilley

  DOI：10.1021/jo802171t

  日期：2009.1.16

  A series of 2,7-substituted hexafluoro-9-heterofluorenes was synthesized via nucleophilic aromatic substitution (SNArF) reactions of phenyllithium, thienyllithium, and lithium phenylacetylide with various octafluoroheterofluorenes and 2,2'-dibromooctafluorobiphenyl. These compounds are of interest as possible building blocks for materials with useful electron transport properties, since they possess relatively low LUMO energy levels. The HOMO-LUMO energy gaps, as determined by UV-vis spectroscopy, range between 3.0 and 3.9 eV, while photoluminescence emission spectra reveal lambda(ems) values in the range of 365 to 420 nm (corresponding to ultraviolet to violet/blue emission). Dilute solution state quantum yields vary significantly with the nature of the heteroatom and the 2,7-substituents, and approach unity for a number of the di(phenylethynyl) derivatives. The experimentally determined LUMO energy levels (-2.7 to -3.3 eV as determined by differential pulse voltammetry) suggest that these compounds may be good candidates for electron transport applications. Single-crystal X-ray analyses of a number of compounds revealed cofacial packing in all cases, with intermolecular distances as short as 3.4 angstrom.