9-bromo-6-butyl-6H-indolo[2,3-b]quinoxaline | 327061-54-1

• 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: 9-bromo-6-butyl-6H-indolo[2,3-b]quinoxaline
• 英文别名: 9-bromo-6-butyl-6H-indolo[3,2-b]quinoxaline；9-bromo-6-butylindolo[3,2-b]quinoxaline
• CAS: 327061-54-1
• 化学式: C₁₈H₁₆BrN₃
• mdl: MFCD02129636
• 分子量: 354.249
• InChiKey: RSJAANYONBCYDG-UHFFFAOYSA-N

物化性质

• 沸点：
  524.1±50.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  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 二苯醚 、 甲苯 为溶剂， 反应 42.0h， 生成 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：

  6H-吲哚并[2,3-b]喹喔啉 在 N-溴代丁二酰亚胺(NBS) 、 苄基三乙基氯化铵 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 36.0h， 生成 9-bromo-6-butyl-6H-indolo[2,3-b]quinoxaline
  参考文献：
  名称：

  Synthesis, Spectra, and Theoretical Investigations of the Triarylamines Based on 6H-Indolo[2,3-b]quinoxaline

  摘要：

  Triarylamines containing a 6H-indolo[2,3-b]quinoxaline core and aromatic units such as phenyl, naphthyl, pyrene, anthracene, or fluorene have been synthesized by employing palladium-catalyzed C-N and C-C coupling reactions and characterized by optical absorption and emission spectra, electrochemical behavior, and thermal studies. Even though the electronic absorption spectra of the compounds were influenced by the nature of the peripheral amines, the emission spectra indicated close similarity for the excited states in these compounds. For the derivatives in which the amines were directly anchored on the 6H-indolo[2,3-b]quinoxaline nucleus, the emission appeared to be dominated by the state localized on the 6H-indolo[2,3-b]quinoxaline chromophore, while in the compounds containing the extended conjugation the fluorescence originated from the polyaromatic linker. The compounds displayed green or yellow emission depending on the nature of the amine segment. All of the dyes displayed one-electron quasi-reversible oxidation couple in the cyclic voltammograms, which is attributable to the oxidation of the peripheral amines at the 6H-indolo[2,3-b]-quinoxaline core. An additional one-electron oxidation process observable at the high positive potentials for the compounds 7 and 8 probably arises from the oxidation of the arylthiophene segment. The enhanced thermal stability and relatively higher glass transition temperatures observed for these compounds were attributed to the presence of dipolar 6H-indolo[2,3-b]quinox. aline segment. The origin of the optical spectra and the trends observed therein were rationalized using TDDFT simulations.

  DOI：

  10.1021/jo1016663

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。
• Enhancement of Interfacial Properties by Indoloquinoxaline‐Based Small Molecules for Highly Efficient Wide‐Bandgap Perovskite Solar Cells
  作者：Jihye Yong、Yu Kyung Lee、Hansol Park、Senthilkumar Muthu、Juhwan Shin、Dong Ryeol Whang、Bong‐Gi Kim、Dong Wook Chang、Hui Joon Park

  DOI：10.1002/adfm.202312505

  日期：2024.4

  Interfacial engineering in organic–inorganic hybrid perovskite solar cells (PSCs) has attracted significant attention, aiming to achieve high‐performing and highly stable devices. Here, newly designed organic small molecules based on quinoxaline and triphenylamine for inverted type wide‐bandgap PSCs are introduced, with the objective of enhancing the interfacial properties between perovskite and NiO_x hole transport layer (HTL). The incorporation of an organic interlayer effectively reduces the energy level offset between the HTL and wide‐bandgap perovskite, while passivating defects within the perovskite layer. It leads to improved charge extraction and minimized non‐radiative recombination at the interface. Furthermore, the enhanced interfacial characteristics and hydrophobicity contribute to the improvement of perovskite film quality, resulting in larger grain size and higher crystallinity. As a result, the power conversion efficiency (PCE) of the PSC is enhanced from 18.9% to 20.1% with the incorporation of the IQTPAFlu interlayer, accompanied by an increase in V_oc to ≈1.3 V, achieving a significantly low V_oc deficit of 0.46 V. And the IQTPAFlu‐based devices demonstrate stable and consistent performance over 500 h, with ≈91% of their initial PCE retained. The highly stable wide‐bandgap PSCs, characterized by high V_oc and PCEs, hold great promise as potential candidates for tandem solar cells.

  摘要有机-无机混合包晶太阳能电池（PSCs）中的界面工程已引起人们的极大关注，其目的是实现高性能和高稳定性的器件。本文介绍了新设计的基于喹喔啉和三苯胺的有机小分子，用于反相型宽带隙 PSCs，目的是增强过氧化物和氧化镍空穴传输层（HTL）之间的界面性能。有机中间膜的加入有效降低了 HTL 与宽带隙磷酸盐之间的能级偏移，同时钝化了磷酸盐层内的缺陷。它改善了电荷萃取，最大程度地减少了界面上的非辐射重组。此外，界面特性和疏水性的增强也有助于提高透辉石薄膜的质量，从而使晶粒尺寸更大、结晶度更高。因此，在加入 IQTPAFlu 中间膜后，PSC 的功率转换效率 (PCE) 从 18.9% 提高到 20.1%，同时 Voc 也提高到 ≈1.3 V，实现了 0.46 V 的显著低 Voc 缺口。基于 IQTPAFlu 的器件在 500 小时内表现出稳定一致的性能，保留了≈91% 的初始 PCE。这种高度稳定的宽带隙 PSC 具有高 Voc 和 PCE 的特点，有望成为串联太阳能电池的潜在候选器件。
• Synthesis, Spectra, and Theoretical Investigations of the Triarylamines Based on 6<i>H</i>-Indolo[2,3-<i>b</i>]quinoxaline
  作者：K. R. Justin Thomas、Payal Tyagi

  DOI：10.1021/jo1016663

  日期：2010.12.3

  Triarylamines containing a 6H-indolo[2,3-b]quinoxaline core and aromatic units such as phenyl, naphthyl, pyrene, anthracene, or fluorene have been synthesized by employing palladium-catalyzed C-N and C-C coupling reactions and characterized by optical absorption and emission spectra, electrochemical behavior, and thermal studies. Even though the electronic absorption spectra of the compounds were influenced by the nature of the peripheral amines, the emission spectra indicated close similarity for the excited states in these compounds. For the derivatives in which the amines were directly anchored on the 6H-indolo[2,3-b]quinoxaline nucleus, the emission appeared to be dominated by the state localized on the 6H-indolo[2,3-b]quinoxaline chromophore, while in the compounds containing the extended conjugation the fluorescence originated from the polyaromatic linker. The compounds displayed green or yellow emission depending on the nature of the amine segment. All of the dyes displayed one-electron quasi-reversible oxidation couple in the cyclic voltammograms, which is attributable to the oxidation of the peripheral amines at the 6H-indolo[2,3-b]-quinoxaline core. An additional one-electron oxidation process observable at the high positive potentials for the compounds 7 and 8 probably arises from the oxidation of the arylthiophene segment. The enhanced thermal stability and relatively higher glass transition temperatures observed for these compounds were attributed to the presence of dipolar 6H-indolo[2,3-b]quinox. aline segment. The origin of the optical spectra and the trends observed therein were rationalized using TDDFT simulations.
• 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.