6,7,8,9-tetrafluoro-1,4-dihydroxyanthraquinone | 859849-46-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 6,7,8,9-tetrafluoro-1,4-dihydroxyanthraquinone
• 英文别名: 5,6,7,8-tetrafluoro-1,4-dihydroxyanthracene；5,6,7,8-Tetrafluoroanthracene-1,4-diol；5,6,7,8-tetrafluoroanthracene-1,4-diol
• CAS: 859849-46-0
• 化学式: C₁₄H₆F₄O₂
• 分子量: 282.194
• InChiKey: HXWPFCKHNZDMML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6,7,8,9-tetrafluoro-1,4-dihydroxyanthraquinone 在 air 作用下， 生成 5,6,7,8-四氟-1,4-蒽二酮
  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
• 作为产物：
  描述：

  3,4,5,6-四氟-1,2-苯二甲醇 在 氢溴酸 、 potassium iodide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 6,7,8,9-tetrafluoro-1,4-dihydroxyanthraquinone
  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

• Synthesis and charge transport studies of stable, soluble hexacenes
  作者：Balaji Purushothaman、Sean R. Parkin、Mark J. Kendrick、Daniel David、Jeremy W. Ward、Liyang Yu、Natalie Stingelin、Oana D. Jurchescu、Oksana Ostroverkhova、John E. Anthony

  DOI：10.1039/c2cc33919f

  日期：——

  predicted to possess enticing electronic properties, but are insoluble and prone to rapid decomposition. Utilizing a combination of functionalization strategies, we present stable, solution-processable hexacenes and an evaluation of their hole and electron transport properties.

  预计大于并五苯的并苯具有诱人的电子性能，但不溶且易于快速分解。利用功能化策略的组合，我们提出了稳定的，可溶液处理的六价金属，并对其空穴和电子传输性质进行了评估。
• Ambipolar, High Performance, Acene-Based Organic Thin Film Transistors
  作者：Ming L. Tang、Anna D. Reichardt、Nobuyuki Miyaki、Randall M. Stoltenberg、Zhenan Bao

  DOI：10.1021/ja8005918

  日期：2008.5.1

  We present a high performance, ambipolar organic field-effect transistor composed of a single material. Ambipolar molecules are rare, and they can enable low-power complementary-like circuits. This low band gap, asymmetric linear acene contains electron-withdrawing fluorine atoms, which lower the C; molecular orbital energies, allowing the injection of electrons. While hole and electron mobilities of up to 0.071 and 0.37 cm(2)/ V center dot s, respectively, are reported on devices measured in nitrogen, hole mobilities of up to 0.12 cm(2)/V center dot s were found in ambient, with electron transport quenched. These devices were fabricated on octadecyltrimethoxysilane-treated surfaces at a substrate temperature of 60 degrees C.
• 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.