bis[N-(2-ethylhexyl)-carbazole-3-yl] | 944925-53-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: bis[N-(2-ethylhexyl)-carbazole-3-yl]
• 英文别名: 9,9'-(2-Ethylhexyl)-9H,9'H-3,3'bicarbazole；9-(2-ethylhexyl)-3-[9-(2-ethylhexyl)carbazol-3-yl]carbazole
• CAS: 944925-53-5
• 化学式: C₄₀H₄₈N₂
• 分子量: 556.835
• InChiKey: TTZNNDYEAIMUAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.5
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  9.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  bis[N-(2-ethylhexyl)-carbazole-3-yl] 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以86%的产率得到bis[6-bromo-N-(2-ethylhexyl)carbazole-3-yl]
  参考文献：
  名称：

  Synthesis and characterization of high Tg carbazole-based amorphous hole-transporting materials for organic light-emitting devices

  摘要：

  Novel hole-transporting materials based on carbazole dendrimers, namely G1CBC and G2CBC were synthesized and characterized. They are thermally stable with high glass transition temperatures (T-g) up to 245 degrees C and exhibit chemically-stable redox processes. Double-layer green OLEDs using these materials as the hole-transporting layer (HTL) with the device configuration of ITO/HTL/Alq3/LiF:Al emit brightly (lambda(em) 522-534 nm) from the Alq3 layer with a maximum luminance and low turn-on voltage of 15,890 cd/m(2) and 3.0 V. respectively. Their ability as HTLs in terms of device performance is comparable to the common hole-transporter N,N'-diphenyl-N,N'-bis(1-naphthyl)-(1,1'-biphenyl)-4,4'-diamine (NPB), however their thermal properties were far greater than both NPB and N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)benzidine (TPD). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.002
• 作为产物：
  描述：

  9-(2-乙基己基)咔唑 在 三氯化铁 作用下， 以 氯仿 为溶剂， 反应 12.0h， 生成 bis[N-(2-ethylhexyl)-carbazole-3-yl]
  参考文献：
  名称：

  Alternating Copolymers ofN-(2-Ethylhexyl)-Carbazole Derivatives with Aniline Units: Synthesis and Properties

  摘要：

  DOI：

  10.1080/15421400600932272

文献信息

• Oxidative Ring Opening of 1,3-Diarylbenzo[c]heterocycles Using m-CPBA: Preparation of 1,2-Diaroylbenzenes
  作者：Meganathan Nandakumar、Ramakrishnan Sivasakthikumaran、Arasambattu K. Mohanakrishnan

  DOI：10.1002/ejoc.201200311

  日期：2012.7

  An unprecedented oxidative cleavage of benzo[c]heterocycles using m-CPBA is reported. The reaction of 1,3-diaryl benzo[c]heterocycles with m-CPBA (meta-chloroperoxybenzoic acid) at room temperature for 5 min led to the formation of 1,2-diaroylbenzenes in good to excellent yields.

  报道了使用 m-CPBA 对苯并 [c] 杂环进行前所未有的氧化裂解。1,3-二芳基苯并 [c] 杂环与 m-CPBA（间氯过氧苯甲酸）在室温下反应 5 分钟，以良好到极好的产率形成 1,2-二芳基苯。
• Nine-ring angular fused biscarbazoloanthracene displaying a solid state based excimer emission suitable for OLED application
  作者：Gleb V. Baryshnikov、Pawel Gawrys、Khrystyna Ivaniuk、Bernhard Witulski、Richard J. Whitby、Ayham Al-Muhammad、Boris Minaev、Vladyslav Cherpak、Pavlo Stakhira、Dmytro Volyniuk、Gabriela Wiosna-Salyga、Beata Luszczynska、Algirdas Lazauskas、Sigitas Tamulevicius、Juozas V. Grazulevicius

  DOI：10.1039/c6tc01469k

  日期：——

  nine fused aromatic rings, including two pyrrole units, has been obtained in a straightforward and convergent synthesis. Computational chemistry and conformational analysis revealed that the semiconductor's molecule is not planar, the two carbazole moieties being helical twisted from the plane of the anthracene unit. Photophysical and electrochemical measurements showed that this angular fused heteroacene

  一种新的双咔唑并蒽由九个稠合的芳族环组成，包括两个吡咯单元，已通过简单且会聚的合成方法获得。计算化学和构象分析表明，半导体分子不是平面的，两个咔唑部分是从蒽单元的平面螺旋形扭曲的。光物理和电化学测量表明，尽管其扩展的π共轭分子框架，该角型稠合杂并苯具有低的HOMO能级和宽的带隙。基于其相对较低的HOMO水平，与其他相关的线性稠合并苯和杂并苯相比，该半导体具有较高的环境稳定性。双咔唑并蒽已被用作白色发光二极管（WOLED）中的发光层。提出白色OLED特征是由于来自活性半导体层的双重发光特性是基于小分子的分子发光和通过合适的固态聚集体而可能的离散的准分子发射。值得注意的是，这是在小分子杂并苯而不是低聚物或聚合物中观察到的这种行为的第一个报道实例。
• Alternating Copolymers of<i>N</i>-(2-Ethylhexyl)-Carbazole Derivatives with Aniline Units: Synthesis and Properties
  作者：Hui Wang、Jeong-Tak Ryu、Yoon Soo Han、Dae-Hwan Kim、Byeong Dae Choi、Lee Soon Park、Younghwan Kwon

  DOI：10.1080/15421400600932272

  日期：2006.12
• 3,3′-Bicarbazolyl-Containing Oxirane and its Reaction Products as New Glass-Forming Electroactive Materials
  作者：V. Vaitkeviciene、J. V. Grazulevicius、V. Jankauskas

  DOI：10.1080/15421400802462938

  日期：2008.12.3

  Low-molar-mass oxiranyl-substituted 3,3'-bicarbazolyl derivatives were synthesized by the reaction of 3,3'-bicarbazolyl-containing oxirane with dimercapto compounds as linking agents. The cationic ring opening polymerization of oxirane monomers was performed using ytterbium (III) trifluoromethanesulfonate [Yb(OTf)(3)] as a cationic initiator to obtain polyether. The full characterization of the compounds by mass spectrometry, IR, H-1 NMR, and C-13 NMR is presented. All the compounds represent amorphous materials with glass transition temperatures ranging from 28 degrees C to 112 C and with 5%-weight-loss temperatures exceeding 308 degrees C. The electron photoemission spectra of the materials were recorded, and the ionization potentials of ca. 5.5 eV were established. Time-of-flight hole drift mobilities of the a morph oils film of some synthesized compounds exceed 10(-5) cm(2)/Vs at high electric fields.
• Synthesis and characterization of hole transporting materials containing bis(carbazole) groups for solid-state dye-sensitized solar cells
  作者：Suran Jung、Younghwan Kwon

  DOI：10.1080/15421406.2021.1972220

  日期：2022.2.11