1,2,3,4,8,9,10,11-octafluoro-6,13-pentacenequinone | 859849-48-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 并五苯醌
• 英文名称: 1,2,3,4,8,9,10,11-octafluoro-6,13-pentacenequinone
• 英文别名: 1,2,3,4,8,9,10,11-octafluoropentacene-6,13-dione；1,2,3,4,8,9,10,11-octafluoro-pentacene-6,13-quinone；1,2,3,4,8,9,10,11-Octafluoropentacene-6,13-dione
• CAS: 859849-48-2
• 化学式: C₂₂H₄F₈O₂
• 分子量: 452.26
• InChiKey: KJEMTYVBZKVKSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  32
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,2,3,4,8,9,10,11-octafluoro-6,13-pentacenequinone 、 triisobutylsilylacetylene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Role of crystallinity of non-fullerene acceptors in bulk heterojunctions

  摘要：

  在BHJ太阳能电池中，基于五环并芘的受体的结晶度的作用得到了阐明。三明治鲱鱼骨骼结构的堆积方式比同面堆积方式具有更高的性能。

  DOI：

  10.1039/c5ta01206f
• 作为产物：
  描述：

  1,2-双(溴甲基)-3,4,5,6-四氟苯 在 air 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 1,2,3,4,8,9,10,11-octafluoro-6,13-pentacenequinone
  参考文献：
  名称：

  Synthesis and Characterization of Electron-Deficient Pentacenes

  摘要：

  Halogen functional groups on pentacene can be used both as synthetic handles for further functionalization as well as to tune the pi-stacking in these systems. The halogenated pentacene derivatives described here (X = Br, X' = H, and X = X' = F) are all stable and soluble, with reduction potentials significantly lower than that of the parent functionalized pentacene (X = X' = H). The bromopentacenes could be further elucidated to pentacene nitriles, further decreasing the acene's reduction potential, while the charge-carrier mobility in the fluorinated systems was shown to scale with the degree of fluorine substitution.

  DOI：

  10.1021/ol050872b

文献信息

• Unusual Molecular Conformations in Fluorinated, Contorted Hexabenzocoronenes
  作者：Yueh-Lin Loo、Anna M. Hiszpanski、Bumjung Kim、Sujun Wei、Chien-Yang Chiu、Michael L. Steigerwald、Colin Nuckolls

  DOI：10.1021/ol102016m

  日期：2010.11.5

  contorted hexabenzocoronenes (HBCs) have been synthesized in a facile manner via Suzuki−Miyaura coupling of fluorinated phenyl boronic acids followed by photocyclization and Scholl cyclization. In addition to the molecular conformation observed in previous HBC derivatives, close-contact fluorine−fluorine intramolecular interactions result in a metastable conformation not previously observed. Heating the

  氟化，扭曲的六苯并甲酮（HBC）通过氟化苯硼酸的Suzuki-Miyaura偶联，光环化和Scholl环化以一种简便的方式合成。除了在以前的HBC衍生物中观察到的分子构象之外，紧密接触的氟-氟分子内相互作用还导致以前未观察到的亚稳态构象。将亚稳HBC加热至100°C以上不可逆地将其转变为稳定构象，这表明亚稳构象源自环化过程中的动力学停滞状态。
• Synthesis and Characterization of Electron-Deficient Pentacenes
  作者：Christopher R. Swartz、Sean R. Parkin、Joseph E. Bullock、John E. Anthony、Alex C. Mayer、George G. Malliaras

  DOI：10.1021/ol050872b

  日期：2005.7.1

  Halogen functional groups on pentacene can be used both as synthetic handles for further functionalization as well as to tune the pi-stacking in these systems. The halogenated pentacene derivatives described here (X = Br, X' = H, and X = X' = F) are all stable and soluble, with reduction potentials significantly lower than that of the parent functionalized pentacene (X = X' = H). The bromopentacenes could be further elucidated to pentacene nitriles, further decreasing the acene's reduction potential, while the charge-carrier mobility in the fluorinated systems was shown to scale with the degree of fluorine substitution.
• Role of crystallinity of non-fullerene acceptors in bulk heterojunctions
  作者：Jes B. Sherman、Balaji Purushothaman、Sean R. Parkin、Chunki Kim、Sam Collins、John Anthony、Thuc-Quyen Nguyen、Michael L. Chabinyc

  DOI：10.1039/c5ta01206f

  日期：——

  The role of crystallinity of pentancene-based acceptors in BHJ solar cells is elucidated. The sandwich herringbone packing motif leads to higher performance than cofacial packing.

  在BHJ太阳能电池中，基于五环并芘的受体的结晶度的作用得到了阐明。三明治鲱鱼骨骼结构的堆积方式比同面堆积方式具有更高的性能。