1-azapentacene-6,13-quinone | 1256375-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: 1-azapentacene-6,13-quinone
• CAS: 1256375-25-3
• 化学式: C₂₁H₁₁NO₂
• 分子量: 309.324
• InChiKey: IKQVKOVUDMWQGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  24.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.03
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-azapentacene-6,13-quinone 、 三异丙基硅基乙炔 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.67h， 以31 mg的产率得到6,13-bis(triisoprpylsilylethynyl)-1-azapentacene
  参考文献：
  名称：

  High and Balanced Hole and Electron Mobilities from Ambipolar Thin-Film Transistors Based on Nitrogen-Containing Oligoacences

  摘要：

  We demonstrate a strategy for designing high-performance, ambipolar, acene-based field-effect transistor (FET) materials, which is based on the replacement of C H moieties by nitrogen atoms in oligoacenes. By using this strategy, two organic semiconductors, 6,13-bis(triisopropylsilylethynyl)anthradipyridine (1) and 8,9,10,11-tetrafluoro-6,13-bis(triisopropylsilylethynyl)-1-azapentacene (3), were synthesized and their FET characteristics studied. Both materials exhibit high and balanced hole and electron mobilities, 1 having mu(h) and mu(e) of 0.11 and 0.15 cm(2)/V.s and 3 having mu(h) and mu(e) of 0.08 and 0.09 cm(2)/V.s, respectively. The successful demonstration of high and balanced ambipolar FET properties from nitrogen-containing oligoacenes opens up new opportunities for designing high-performance ambipolar organic semiconductors.

  DOI：

  10.1021/ja107046s
• 作为产物：
  描述：

  2,3-bis(dibromomethyl)pyridine 、 1,4-蒽醌 在 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以45%的产率得到1-azapentacene-6,13-quinone
  参考文献：
  名称：

  High and Balanced Hole and Electron Mobilities from Ambipolar Thin-Film Transistors Based on Nitrogen-Containing Oligoacences

  摘要：

  We demonstrate a strategy for designing high-performance, ambipolar, acene-based field-effect transistor (FET) materials, which is based on the replacement of C H moieties by nitrogen atoms in oligoacenes. By using this strategy, two organic semiconductors, 6,13-bis(triisopropylsilylethynyl)anthradipyridine (1) and 8,9,10,11-tetrafluoro-6,13-bis(triisopropylsilylethynyl)-1-azapentacene (3), were synthesized and their FET characteristics studied. Both materials exhibit high and balanced hole and electron mobilities, 1 having mu(h) and mu(e) of 0.11 and 0.15 cm(2)/V.s and 3 having mu(h) and mu(e) of 0.08 and 0.09 cm(2)/V.s, respectively. The successful demonstration of high and balanced ambipolar FET properties from nitrogen-containing oligoacenes opens up new opportunities for designing high-performance ambipolar organic semiconductors.

  DOI：

  10.1021/ja107046s