diphenyl 2,2'-(octafluoro biphenyl) silane | 17051-11-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: diphenyl 2,2'-(octafluoro biphenyl) silane
• 英文别名: 9,9-diphenyl-octafluorosilafluorene；1,2,3,4,6,7,8,9-octafluoro-5,5-diphenyl-5H-dibenzosilole；Diphenyl-octafluorbiphenylen-silan；1,2,3,4,6,7,8,9-Octafluoro-5,5-diphenylbenzo[b][1]benzosilole；1,2,3,4,6,7,8,9-octafluoro-5,5-diphenylbenzo[b][1]benzosilole
• CAS: 17051-11-5
• 化学式: C₂₄H₁₀F₈Si
• 分子量: 478.416
• InChiKey: SNBRSOOGHIXVKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-噻吩基锂 、 diphenyl 2,2'-(octafluoro biphenyl) silane 以 乙醚 、 甲苯 为溶剂， 反应 12.0h， 以52%的产率得到2,7-dithienyl-9,9-diphenyl-hexafluorosilafluorene
  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
• 作为产物：
  描述：

  2,2'-dibromooctafluorobiphenyl 、 二苯二氯硅烷 在 正丁基锂 作用下， 以 乙醚 、 正己烷 、 四氢呋喃 为溶剂， 反应 10.0h， 以50%的产率得到diphenyl 2,2'-(octafluoro biphenyl) silane
  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

• Perfluorophenyl derivatives of the elements
  作者：S.C. Cohen、A.G. Massey

  DOI：10.1016/s0022-328x(00)83172-1

  日期：1967.12

  The preparations and reactions of several 2,2′-disubstituted octafluorobiphenyls and heterocyclic organometallic derivatives of Group IV elements and titanium are described. Some evidence is given for the organometallic titanium intermediate postulated in the coupling reaction for the syntheses of polyfluorobiphenyls.

  描述了几种2,2'-二取代的八氟联苯和Ⅳ族元素的杂环有机金属衍生物以及钛的制备和反应。对于在多氟联苯的合成的偶联反应中假定的有机金属钛中间体，给出了一些证据。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.4, 1.3.3.7, page 17 - 32
  作者：

  DOI：——

  日期：——
• 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.