9-hexyl-9H-carbazole-3-carbonitrile | 1332585-81-5

• 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: 9-hexyl-9H-carbazole-3-carbonitrile
• 英文别名: 3-cyano-9-hexyl-9H-carbazole
• CAS: 1332585-81-5
• 化学式: C₁₉H₂₀N₂
• 分子量: 276.381
• InChiKey: HYNCHYITLFQNGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.25
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  28.72
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  9-hexyl-9H-carbazole-3-carbonitrile 在 吡啶 、 sodium azide 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 78.0h， 生成 3-(5-(4-(pyridin-2-yl)phenyl)-1,3,4-oxadiazol-2-yl)-9-hexyl-9H-carbazole
  参考文献：
  名称：

  Novel yellow phosphorescent iridium complexes containing a carbazole–oxadiazole unit used in polymeric light-emitting diodes

  摘要：

  Yellow iridium complexes Ir(PPOHC)(3) and (PPOHC)(2)Ir(acac) (PPOHC: 3-(5-(4-(pyridin-2-yl)phenyl)-1,3,4-oxadiazol-2-yl)-9-hexyl-9H-carbazole) were synthesized and characterized. The Ir(PPOHC)(3) complex has good thermal stability with 5% weight-reduction occurring at 370 degrees C and a glass-transition temperature of 201 degrees C. A polymeric light-emitting diode using the Ir(PPOHC)(3) complex as a phosphorescent dopant showed a luminance efficiency of 16.4 cd/A and the maximum external quantum efficiency of 6.6% with CIE coordinates of (0.50, 0.49). A white polymeric light-emitting diode was fabricated using Ir(PPOHC)(3) which showed a luminance efficiency of 15.3 cd/A, with CIE coordinates of (0.39, 0.44). These results indicate that the iridium complexes containing a linked carbazole-oxadiazole unit are promising candidates in high-efficiency electroluminescent devices. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.04.005
• 作为产物：
  描述：

  N-hexylcarbazole 在 ammonium hydroxide 、 碘 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 7.5h， 生成 9-hexyl-9H-carbazole-3-carbonitrile
  参考文献：
  名称：

  Novel yellow phosphorescent iridium complexes containing a carbazole–oxadiazole unit used in polymeric light-emitting diodes

  摘要：

  Yellow iridium complexes Ir(PPOHC)(3) and (PPOHC)(2)Ir(acac) (PPOHC: 3-(5-(4-(pyridin-2-yl)phenyl)-1,3,4-oxadiazol-2-yl)-9-hexyl-9H-carbazole) were synthesized and characterized. The Ir(PPOHC)(3) complex has good thermal stability with 5% weight-reduction occurring at 370 degrees C and a glass-transition temperature of 201 degrees C. A polymeric light-emitting diode using the Ir(PPOHC)(3) complex as a phosphorescent dopant showed a luminance efficiency of 16.4 cd/A and the maximum external quantum efficiency of 6.6% with CIE coordinates of (0.50, 0.49). A white polymeric light-emitting diode was fabricated using Ir(PPOHC)(3) which showed a luminance efficiency of 15.3 cd/A, with CIE coordinates of (0.39, 0.44). These results indicate that the iridium complexes containing a linked carbazole-oxadiazole unit are promising candidates in high-efficiency electroluminescent devices. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.04.005

文献信息

• Oxidative Coupling of Carbazoles: A Substituent-Governed Regioselectivity Profile
  作者：Sudesh Mallick、Sudhakar Maddala、Kalidass Kollimalayan、Parthasarathy Venkatakrishnan

  DOI：10.1021/acs.joc.8b02322

  日期：2019.1.4

  (metal-free) recyclable oxidants, such as DDQ or CA/H+, for accessing bicarbazole regioisomers. Differently substituted carbazoles are examined to showcase regioselective discrimination (3,3′- versus 1,3′-bicarbazoles) and preferences based on sterics and electronics in oxidative coupling. Finally, a mechanism that involves the carbazole radical cation has been traced (evidenced) and proposed on the basis of the

  在存在有机（无金属）可循环使用的氧化剂（例如DDQ或CA / H +）的情况下，具有各种取代基的咔唑的氧化C-C偶联反应证明了该化合物可与联咔唑区域异构体接触。对不同取代的咔唑进行了研究，以显示区域选择性的区别（3,3'-与1,3'-联咔唑）和在氧化偶联中基于空间和电子学的偏好。最终，已经找到（证明）了涉及咔唑自由基阳离子的机理，并在紫外可见近红外吸收和EPR光谱结果的基础上提出了一种机理。这项研究强调了以有效方式对一系列联咔唑进行战略化学制备的方法。
• The Ugi four-component reaction as a concise modular synthetic tool for photo-induced electron transfer donor-anthraquinone dyads
  作者：Sarah Bay、Gamall Makhloufi、Christoph Janiak、Thomas J J Müller

  DOI：10.3762/bjoc.10.100

  日期：——

  Phenothiazinyl and carbazolyl-donor moieties can be covalently coupled to an anthraquinone acceptor unit through an Ugi four-component reaction in a rapid, highly convergent fashion and with moderate to good yields. These novel donor–acceptor dyads are electronically decoupled in the electronic ground state according to UV–vis spectroscopy and cyclic voltammetry. However, in the excited state the inherent donor luminescence is efficiently quenched. Previously performed femtosecond spectroscopic measurements account for a rapid exergonic depopulation of the excited singlet states into a charge-separated state. Calculations of the Gibbs energy of photo-induced electron transfer from readily available UV–vis spectroscopic and cyclovoltammetric data applying the Weller approximation enables a quick evaluation of these novel donor–acceptor dyads. In addition, the X-ray structure of a phenothiazinyl–anthraquinone dyad supports short donor–acceptor distances by an intramolecular π-stacking conformation, an important assumption also implied in the calculations of the Gibbs energies according to the Weller approximation.

  苯并噻唑基和咔唑基供体基团可以通过Ugi四组分反应与蒽醌受体单元共价耦合，快速、高度收敛且产率中等至良好。这些新颖的供体-受体二元体在电子基态下根据紫外-可见光谱和循环伏安法电子解耦。然而，在激发态下，内在的供体发光被有效地猝灭。先前进行的飞秒光谱测量解释了激发单重态迅速放出能量进入电荷分离态。利用Weller近似法从易得的紫外-可见光谱和循环伏安法数据计算光致电子转移的吉布斯自由能，可以快速评估这些新颖的供体-受体二元体。此外，苯并噻唑-蒽醌二元体的X射线结构支持分子内π-堆积构象的短供体-受体距离，这也是Weller近似法计算吉布斯自由能的重要假设。