1-bromo-3,6-di-tert-butyl-9-ethyl-9H-carbazole | 1401428-83-8

• 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: 1-bromo-3,6-di-tert-butyl-9-ethyl-9H-carbazole
• 英文别名: N-ethylcarbazole；1-Bromo-3,6-ditert-butyl-9-ethylcarbazole；1-bromo-3,6-ditert-butyl-9-ethylcarbazole
• CAS: 1401428-83-8
• 化学式: C₂₂H₂₈BrN
• 分子量: 386.375
• InChiKey: CLYGHJVGIRKIFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-bromo-3,6-di-tert-butyl-9-ethyl-9H-carbazole 在 正丁基锂 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 生成 3,6-ditert-butyl-1-[2-(3,6-ditert-butyl-9-ethylcarbazol-1-yl)ethenyl]-9-ethylcarbazole
  参考文献：
  名称：

  联咔唑：一系列共轭咔唑二聚体的系统结构-性质研究

  摘要：

  一个大系列缀合咔唑二聚物，即bicarbazoles 1 - 12中，通过铃木-宫浦，薗头，干草，和的McMurry偶联反应合成。在1 – 12中，两个咔唑部分在1、2或3位上直接连接或通过炔或烯烃间隔基连接。结构与性质之间的关系，尤其是共轭连接性和π共轭间隔基对1 – 12的电子，光物理和电化学性质的影响通过广泛的紫外可见光谱和荧光光谱测量，循环伏安法（CV），理论计算以及X射线晶体学分析研究了。咔唑在1位上的连接可确保高度的π共轭，而在3位上的连接则可增强供电子能力。炔间隔基和烯烃间隔基都允许π共轭的扩展，后者也引起供体能力的增加。此外，发现结构变化显着影响荧光量子产率，其高达0.84。

  DOI：

  10.1021/jo3016538
• 作为产物：
  描述：

  3,6-二叔丁基咔唑 在 N-溴代丁二酰亚胺(NBS) 、 四丁基溴化铵 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 4.25h， 生成 1-bromo-3,6-di-tert-butyl-9-ethyl-9H-carbazole
  参考文献：
  名称：

  Diphenylaminocarbazoles by 1,8-functionalization of carbazole: Materials and application to phosphorescent organic light-emitting diodes

  摘要：

  A series of novel carbazole-based materials, DPACz1, DPACz2 and DPACz3 having diphenylamino moieties at 1- and 8-positions of carbazole have been synthesized and characterized for the first time. The introduction of diphenylamino substituents at 1- or 1,8-positions of carbazole resulted into increase of the band-gap compared with the previously reported 3,6- or 2,7-substituted ones. The HOMO levels increased from DPACz1 to DPACz2 with the addition of one additional diplienylamino unit, and further increased in case of DPACz3, a dimer of DPACz1 having a benzidine moiety. The materials have high triplet energy levels of 2.68, 2.60 and 2.45 eV, respectively. Based on suitable HOMO levels and high triplet energies, the newly synthesized diphenylaminocabazoles were investigated for their potential as solution-processable host materials for green phosphorescent OLEDs with the device configuration, [ITO/PEDOT:PSS/Emitting layer/TPBi/CsF/Al]. All the devices emitted typical green light with high luminance and had low turn-on voltages along with good luminous efficiencies which were further improved by adjusting charge balance using PBD, as a co-host. The basic characteristics and the preliminary OLED results showed the usefulness of our new materials, and this kind of 1-/1,8-substitution of carbazole would open a new way of materials design. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2015.08.027

文献信息

• Carbazole-BODIPY conjugates: design, synthesis, structure and properties
  作者：Rajneesh Misra、Thaksen Jadhav、Bhausaheb Dhokale、Prabhat Gautam、Rekha Sharma、Ramesh Maragani、Shaikh M. Mobin

  DOI：10.1039/c4dt00983e

  日期：——

  A set of carbazole substituted BODIPYs 2a–2c were designed and synthesized by the Pd-catalysed Sonogashira cross-coupling reaction. The effects of variation in the donor strength of various carbazoles were investigated by photophysical, electrochemical and computational studies. The electronic absorption spectra of BODIPYs 2a and 2c show charge transfer bands, which show red shift in polar solvents

  通过Pd催化的Sonogashira交叉偶联反应设计并合成了一组咔唑取代的BODIPY 2a–2c。通过光物理，电化学和计算研究，研究了各种咔唑供体强度变化的影响。BODIPY 2a和2c的电子吸收光谱显示出电荷转移带，该电荷转移带显示了在极性溶剂中的红移。BODIPY 2a–2c在非极性溶剂中具有强荧光性（从局部状态发射），在极性溶剂中具有弱荧光性（从电荷转移状态发射）。光物理和电化学研究表明咔唑和BODIPY之间强的供体-受体相互作用，并遵循2a阶> 2c > 2b。计算结果与实验结果吻合良好。据报道，BODIPY 2a–2c的单晶结构表现出有趣的超分子相互作用。2a的包装图显示了锯齿形3D结构排列，而2b和2c则显示了复杂的3D结构图案。
• Bicarbazoles: Systematic Structure–Property Investigations on a Series of Conjugated Carbazole Dimers
  作者：Shin-ichiro Kato、Hiroto Noguchi、Atsushi Kobayashi、Toshitada Yoshihara、Seiji Tobita、Yosuke Nakamura

  DOI：10.1021/jo3016538

  日期：2012.10.19

  A large series of conjugated carbazole dimers, namely bicarbazoles 1–12, were synthesized by Suzuki–Miyaura, Sonogashira, Hay, and McMurry coupling reactions. In 1–12, the two carbazole moieties are linked at the 1-, 2-, or 3-position directly or via an acetylenic or olefinic spacer. The structure–property relationships, particularly the effects of the conjugation connectivity and the π-conjugated

  一个大系列缀合咔唑二聚物，即bicarbazoles 1 - 12中，通过铃木-宫浦，薗头，干草，和的McMurry偶联反应合成。在1 – 12中，两个咔唑部分在1、2或3位上直接连接或通过炔或烯烃间隔基连接。结构与性质之间的关系，尤其是共轭连接性和π共轭间隔基对1 – 12的电子，光物理和电化学性质的影响通过广泛的紫外可见光谱和荧光光谱测量，循环伏安法（CV），理论计算以及X射线晶体学分析研究了。咔唑在1位上的连接可确保高度的π共轭，而在3位上的连接则可增强供电子能力。炔间隔基和烯烃间隔基都允许π共轭的扩展，后者也引起供体能力的增加。此外，发现结构变化显着影响荧光量子产率，其高达0.84。
• Diphenylaminocarbazoles by 1,8-functionalization of carbazole: Materials and application to phosphorescent organic light-emitting diodes
  作者：Shahid Ameen、Seul Bee Lee、Sung Cheol Yoon、Jaemin Lee、Changjin Lee

  DOI：10.1016/j.dyepig.2015.08.027

  日期：2016.1

  A series of novel carbazole-based materials, DPACz1, DPACz2 and DPACz3 having diphenylamino moieties at 1- and 8-positions of carbazole have been synthesized and characterized for the first time. The introduction of diphenylamino substituents at 1- or 1,8-positions of carbazole resulted into increase of the band-gap compared with the previously reported 3,6- or 2,7-substituted ones. The HOMO levels increased from DPACz1 to DPACz2 with the addition of one additional diplienylamino unit, and further increased in case of DPACz3, a dimer of DPACz1 having a benzidine moiety. The materials have high triplet energy levels of 2.68, 2.60 and 2.45 eV, respectively. Based on suitable HOMO levels and high triplet energies, the newly synthesized diphenylaminocabazoles were investigated for their potential as solution-processable host materials for green phosphorescent OLEDs with the device configuration, [ITO/PEDOT:PSS/Emitting layer/TPBi/CsF/Al]. All the devices emitted typical green light with high luminance and had low turn-on voltages along with good luminous efficiencies which were further improved by adjusting charge balance using PBD, as a co-host. The basic characteristics and the preliminary OLED results showed the usefulness of our new materials, and this kind of 1-/1,8-substitution of carbazole would open a new way of materials design. (C) 2015 Elsevier Ltd. All rights reserved.