6-Butyl-9-(1,3,4-triphenyltriphenylen-2-yl)indolo[3,2-b]quinoxaline | 1309373-53-2

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 6-Butyl-9-(1,3,4-triphenyltriphenylen-2-yl)indolo[3,2-b]quinoxaline
• CAS: 1309373-53-2
• 化学式: C₅₄H₃₉N₃
• 分子量: 729.924
• InChiKey: HXNNRLSMOJTQNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.4
• 重原子数：
  57
• 可旋转键数：
  7
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  9-bromo-6-butyl-6H-indolo[2,3-b]quinoxaline 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二异丙胺 、 三苯基膦 作用下， 以 二苯醚 为溶剂， 反应 48.0h， 生成 6-Butyl-9-(1,3,4-triphenyltriphenylen-2-yl)indolo[3,2-b]quinoxaline
  参考文献：
  名称：

  Solution Processable Indoloquinoxaline Derivatives Containing Bulky Polyaromatic Hydrocarbons: Synthesis, Optical Spectra, and Electroluminescence

  摘要：

  New hybrid materials featuring the dipolar fragment 6H-indolo[2,3-b]quinoxaline attached to the bulkier polyaromatic hydrocarbons such as fluoranthene, triphenylene, or polyphenylated benzene have been synthesized by a two-step procedure involving Sonogashira and Diels-Alder reactions. They were characterized by absorption, emission, electrochemical, thermal, and theoretical investigations. The electronic properties of the compounds were dominated by the 6H-indolo[2,3-b]quinoxaline chromophore, and the incorporation of polyaromatic hydrocarbons reduces the chances of nonradiative deactivation processes associated with the excited state and improves the emission properties. The compounds displayed cyan emission with moderate quantum efficiency when excited at the absorption maximum. All of the compounds exhibited an irreversible reduction process corresponding to the addition of electron at the quinoxaline segment. They showed moderate thermal stability and glass transition temperature greater than 100 degrees C. The presence of rigid 6H-indolo[2,3-b]quinoxaline and bulkier polyaromatic hydrocarbon segments enhances the thermal stability and glass transition temperature significantly. Finally, the dyes were successfully applied as an electron-transporting and emitting layer in multilayered organic light-emitting diodes comprising a N,N'-bis(1-naphthyl)-N,N'-diphenyl-1,1'-biphenyl-4,4'-diamine hole-transporting layer. The cyan emitting devices were characterized by moderate device performance parameters.

  DOI：

  10.1021/jo2004764

文献信息

• Solution Processable Indoloquinoxaline Derivatives Containing Bulky Polyaromatic Hydrocarbons: Synthesis, Optical Spectra, and Electroluminescence
  作者：Payal Tyagi、A. Venkateswararao、K. R. Justin Thomas

  DOI：10.1021/jo2004764

  日期：2011.6.3

  New hybrid materials featuring the dipolar fragment 6H-indolo[2,3-b]quinoxaline attached to the bulkier polyaromatic hydrocarbons such as fluoranthene, triphenylene, or polyphenylated benzene have been synthesized by a two-step procedure involving Sonogashira and Diels-Alder reactions. They were characterized by absorption, emission, electrochemical, thermal, and theoretical investigations. The electronic properties of the compounds were dominated by the 6H-indolo[2,3-b]quinoxaline chromophore, and the incorporation of polyaromatic hydrocarbons reduces the chances of nonradiative deactivation processes associated with the excited state and improves the emission properties. The compounds displayed cyan emission with moderate quantum efficiency when excited at the absorption maximum. All of the compounds exhibited an irreversible reduction process corresponding to the addition of electron at the quinoxaline segment. They showed moderate thermal stability and glass transition temperature greater than 100 degrees C. The presence of rigid 6H-indolo[2,3-b]quinoxaline and bulkier polyaromatic hydrocarbon segments enhances the thermal stability and glass transition temperature significantly. Finally, the dyes were successfully applied as an electron-transporting and emitting layer in multilayered organic light-emitting diodes comprising a N,N'-bis(1-naphthyl)-N,N'-diphenyl-1,1'-biphenyl-4,4'-diamine hole-transporting layer. The cyan emitting devices were characterized by moderate device performance parameters.