1,4-Bis(pentafluorophenylethynyl)benzene | 258506-15-9

• 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: 1,4-Bis(pentafluorophenylethynyl)benzene
• 英文别名: 1,2,3,4,5-Pentafluoro-6-[2-[4-[2-(2,3,4,5,6-pentafluorophenyl)ethynyl]phenyl]ethynyl]benzene
• CAS: 258506-15-9
• 化学式: C₂₂H₄F₁₀
• 分子量: 458.258
• InChiKey: MSSYWCJGACJNQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  3.0
• 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：
  10

反应信息

• 作为反应物：
  描述：

  [Cp2Zr(η2-Ph2PCCPh)]2 、 1,4-Bis(pentafluorophenylethynyl)benzene 以 甲苯 为溶剂， 以44%的产率得到Cp2Zr[2-Ph2P-3-Ph-4-(C6F5)C4]-1,4-C6H4-Cp2Zr[2-Ph2P-3-Ph-4-(C6F5)C4]
  参考文献：
  名称：

  分离的氧化锆环丙烯与1-炔基膦配体的不对称氧化锆环戊二烯

  摘要：

  1- alkynylphosphines，R一个当量的反应2 PC≡CR'（R =的Et，我Pr或P h和R'= pH或MES），再用Cp 2 Zr的（PYR）（η 2 -Me 3 SiC≡ CSiMe 3）导致单炔配合物的形成。在R = Et，i Pr或Ph且R'= Ph的情况下，会产生“不含配体的”氧化锆环丙烯络合物。这些复合物是通过在二聚复合物的[Cp磷孤对分子间捐赠稳定2的Zr（η 2 -R 2 PC≡CPh）] 2（R =的Et，我Pr或PH）。然而，在R = Ph且R'= Mes的情况下，锆碳环丙烯-吡啶配合物Cp 2（PYR）（η的Zr 2 -Ph 2 PC≡CMes）形成。1-alkynylphosphines的自偶联物通过pH的第二当量的反应表现出2 PC≡CPh用的[Cp 2 Zr的（η 2 -Ph 2 PC≡CPh）] 2，得到的Cp diphosphinozirconacyclopentadiene

  DOI：

  10.1021/om801040t
• 作为产物：
  描述：

  1,4-二乙炔基苯 、 2,3,4,5,6-五氟碘苯 在 copper(l) iodide 、 四(三苯基膦)钯 、 二异丙胺 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以65%的产率得到1,4-Bis(pentafluorophenylethynyl)benzene
  参考文献：
  名称：

  Regioselective Coupling of Pentafluorophenyl Substituted Alkynes:  Mechanistic Insight into the Zirconocene Coupling of Alkynes and a Facile Route to Conjugated Polymers Bearing Electron-Withdrawing Pentafluorophenyl Substituents

  摘要：

  The reaction of Cp2ZrCl2 with 2 equiv of BuLi at -78 degreesC, followed by the addition of an unsymmetrical tetra- or pentafluorophenyl substituted alkyne R(1)CdropCAr(dagger) (R-1, Ar-dagger = (CH2)(4)Me, p-C6F4H; Me, p-C6F4H; Ph, C6F5), resulted in regioselective couplings of these alkynes to zirconacyclopentaclienes in which the Art substituents preferentially adopt the 3,4-positions (betabeta) of the zirconacyclopentacliene ring. With Cp2Zr(py)(Me3SiC=CSiMe3) as the zirconocene reagent, the couplings could be carried out at room temperature; however, at higher temperatures significant quantities of the 2,4-fluoroaryl substituted (alphabeta) isomers were also formed. None of the conditions employed produced the 2,5-fluoroaryl substituted (alphaalpha) isomers. These fluoroaryl-substituted zirconacyclopentadienes were readily converted to butadienes via reactions with acids. The zirconacyclopentacliene Cp2ZrC4-2,5-Ph-2-3+(C6F5)(2), which resulted from the coupling of PhCequivalent toC(C6F5), was converted to the corresponding thiophene by reaction with S2Cl2, and to an arene by reaction with MeO2CC=CCO2Me/CuCl. Mechanistic studies on zirconocene couplings of (p-CF3C6H4)Cequivalent toC(p-MeC6H4) indicate that the observed regioselectivities are determined by an electronic factor that controls the orientation of at least one of the two alkynes as they are coupled. Additionally, these studies suggest an unsymmetrical transition state for the zirconocene coupling of alkynes, and this is supported by DFT calculations. The reaction of [(C6F5)Cequivalent toCCH(2)](2)CH2 with Cp2Zr(py)(Me(3)SiCequivalent toCSiMe(3)) resulted in a zirconacyclopentacliene in which the pentafluorophenyl substituents have been forced into the 2,5-positions (alphaalpha). Zirconocene coupling of the diyne (C6F5)Cequivalent toC-1+C6H4-Cequivalent toC(C6F5) provided a route to conjugated polymers bearing electron-withdrawing pentafluorophenyl groups.

  DOI：

  10.1021/ja0209161

文献信息

• Unsymmetrical Zirconacyclopentadienes from Isolated Zirconacyclopropenes with 1-Alkynylphosphine Ligands
  作者：Adam D. Miller、Samuel A. Johnson、Karl A. Tupper、Jennifer L. McBee、T. Don Tilley

  DOI：10.1021/om801040t

  日期：2009.2.23

  zirconacyclopentadiene Cp2Zr[2-Ph2P-3,4,5-Ph3C4] was converted to the corresponding thiophene oxide by the oxo-transfer reaction with sulfur dioxide. In the case of ((1Z,3E)-3-ethyl-2-phenylhexa-1,3-dienyl)diphenylphosphine and (3,4,5-triphenylthiophen-2-yl oxide)diphenylphosphine, the molecules were isolated as their phosphine oxides. Reactions of the zirconacyclopropene complexes [Cp2Zr(η2-Ph2PC≡CPh)]2 and Cp2

  1- alkynylphosphines，R一个当量的反应2 PC≡CR'（R =的Et，我Pr或P h和R'= pH或MES），再用Cp 2 Zr的（PYR）（η 2 -Me 3 SiC≡ CSiMe 3）导致单炔配合物的形成。在R = Et，i Pr或Ph且R'= Ph的情况下，会产生“不含配体的”氧化锆环丙烯络合物。这些复合物是通过在二聚复合物的[Cp磷孤对分子间捐赠稳定2的Zr（η 2 -R 2 PC≡CPh）] 2（R =的Et，我Pr或PH）。然而，在R = Ph且R'= Mes的情况下，锆碳环丙烯-吡啶配合物Cp 2（PYR）（η的Zr 2 -Ph 2 PC≡CMes）形成。1-alkynylphosphines的自偶联物通过pH的第二当量的反应表现出2 PC≡CPh用的[Cp 2 Zr的（η 2 -Ph 2 PC≡CPh）] 2，得到的Cp diphosphinozirconacyclopentadiene
• ORGANIC THIN FILM TRANSISTOR DEVICE AND ORGANIC THIN FILM LIGHT-EMITTING TRANSISTOR
  申请人：Nakano Yuki

  公开号：US20100012929A1

  公开（公告）日：2010-01-21

  An organic thin film transistor including a substrate having thereon at least three terminals of a gate electrode, a source electrode and a drain electrode, an insulator layer and an organic semiconductor layer, with a current between a source and a drain being controlled upon application of a voltage to the gate electrode, wherein the organic semiconductor layer includes a compound having a specified structure; and an organic thin film light emitting transistor utilizing an organic thin film transistor, wherein the organic thin film transistor is one in which light emission is obtained utilizing a current flowing between the source and the drain, and the light emission is controlled upon application of a voltage to the gate electrode, and is made high with respect to the response speed (driving speed) and has a large ON/OFF ratio, are provided.
• US8217389B2
  申请人：——

  公开号：US8217389B2

  公开（公告）日：2012-07-10
• Regioselective Coupling of Pentafluorophenyl Substituted Alkynes:  Mechanistic Insight into the Zirconocene Coupling of Alkynes and a Facile Route to Conjugated Polymers Bearing Electron-Withdrawing Pentafluorophenyl Substituents
  作者：Samuel A. Johnson、Feng-Quan Liu、Min Chul Suh、Stefan Zürcher、Markus Haufe、Shane S. H. Mao、T. Don Tilley

  DOI：10.1021/ja0209161

  日期：2003.4.1

  The reaction of Cp2ZrCl2 with 2 equiv of BuLi at -78 degreesC, followed by the addition of an unsymmetrical tetra- or pentafluorophenyl substituted alkyne R(1)CdropCAr(dagger) (R-1, Ar-dagger = (CH2)(4)Me, p-C6F4H; Me, p-C6F4H; Ph, C6F5), resulted in regioselective couplings of these alkynes to zirconacyclopentaclienes in which the Art substituents preferentially adopt the 3,4-positions (betabeta) of the zirconacyclopentacliene ring. With Cp2Zr(py)(Me3SiC=CSiMe3) as the zirconocene reagent, the couplings could be carried out at room temperature; however, at higher temperatures significant quantities of the 2,4-fluoroaryl substituted (alphabeta) isomers were also formed. None of the conditions employed produced the 2,5-fluoroaryl substituted (alphaalpha) isomers. These fluoroaryl-substituted zirconacyclopentadienes were readily converted to butadienes via reactions with acids. The zirconacyclopentacliene Cp2ZrC4-2,5-Ph-2-3+(C6F5)(2), which resulted from the coupling of PhCequivalent toC(C6F5), was converted to the corresponding thiophene by reaction with S2Cl2, and to an arene by reaction with MeO2CC=CCO2Me/CuCl. Mechanistic studies on zirconocene couplings of (p-CF3C6H4)Cequivalent toC(p-MeC6H4) indicate that the observed regioselectivities are determined by an electronic factor that controls the orientation of at least one of the two alkynes as they are coupled. Additionally, these studies suggest an unsymmetrical transition state for the zirconocene coupling of alkynes, and this is supported by DFT calculations. The reaction of [(C6F5)Cequivalent toCCH(2)](2)CH2 with Cp2Zr(py)(Me(3)SiCequivalent toCSiMe(3)) resulted in a zirconacyclopentacliene in which the pentafluorophenyl substituents have been forced into the 2,5-positions (alphaalpha). Zirconocene coupling of the diyne (C6F5)Cequivalent toC-1+C6H4-Cequivalent toC(C6F5) provided a route to conjugated polymers bearing electron-withdrawing pentafluorophenyl groups.