6-butyl-9-ethynyl-6H-indolo[2,3-b]quinoxaline | 1309373-46-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 6-butyl-9-ethynyl-6H-indolo[2,3-b]quinoxaline
• 英文别名: 6-butyl-9-ethynyl-6H-indolo[3,2-b]quinoxaline；6-Butyl-9-ethynylindolo[3,2-b]quinoxaline
• CAS: 1309373-46-3
• 化学式: C₂₀H₁₇N₃
• 分子量: 299.375
• InChiKey: YAZGVCLJVVZANE-UHFFFAOYSA-N

物化性质

• 沸点：
  455.9±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7,9-二苯基-8H-环戊并[a]苊烯-8-酮 、 6-butyl-9-ethynyl-6H-indolo[2,3-b]quinoxaline 以 二苯醚 为溶剂， 反应 24.0h， 以95%的产率得到6-Butyl-9-(7,10-diphenylfluoranthen-8-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
• 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 、 三乙胺 、 三苯基膦 、 potassium hydroxide 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 6-butyl-9-ethynyl-6H-indolo[2,3-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

• Organic dyes containing indolo[2,3-b]quinoxaline as a donor: synthesis, optical and photovoltaic properties
  作者：A. Venkateswararao、Payal Tyagi、K.R. Justin Thomas、Ping-Wei Chen、Kuo-Chuan Ho

  DOI：10.1016/j.tet.2014.04.009

  日期：2014.9

  New organic dyes containing indolo[2,3-b]quinoxaline donor have been synthesized for application in dye sensitized solar cells as sensitizers. The dyes exhibited interesting optical properties tuneable by the nature of the conjugation bridge. Origin of the optical transitions in the dyes was corroborated by the TDDFT computations. The LUMO and HOMO of the dyes were found to be favourable for electron

  含有吲哚并[2，3- b ]喹喔啉供体的新型有机染料已被合成用于染料敏化太阳能电池中作为敏化剂。染料表现出令人感兴趣的光学特性，可通过共轭桥的性质对其进行调节。TDDFT计算证实了染料中光学跃迁的起源。发现染料的LUMO和HOMO分别有利于电子注入到TiO 2的导带中以及通过电解质中的氧化还原穿梭而使染料再生。由于染料表现出溶剂相关的吸收性能，DSSC分别从两个不同的染浴溶液，DCM和乙腈/制造叔-丁醇/二甲亚砜混合物。由于间隔良好的染料填充所产生的电荷转移阻力相对较小，因此从较晚的浴液中吸附的染料导致了更好的设备性能。在所有染料中，在π-间隔物中包含噻吩的染料表现出最高的器件效率。
• 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.