1,8-dibromo-3,6-di-tert-butyl-9-ethyl-9H-carbazole | 1016894-26-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,8-dibromo-3,6-di-tert-butyl-9-ethyl-9H-carbazole
• 英文别名: 1,8-Dibromo-3,6-ditert-butyl-9-ethylcarbazole；1,8-dibromo-3,6-ditert-butyl-9-ethylcarbazole
• CAS: 1016894-26-0
• 化学式: C₂₂H₂₇Br₂N
• 分子量: 465.271
• InChiKey: PZSCOTSXUSVLMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  25
• 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：

  1,8-dibromo-3,6-di-tert-butyl-9-ethyl-9H-carbazole 、 噻吩-2-硼酸频哪醇酯 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 12.0h， 以32%的产率得到3,6-di-tert-butyl-1,8-di(2-thienyl)-9-ethyl-9H-carbazole
  参考文献：
  名称：

  Synthesis and Electronic, Photophysical, and Electrochemical Properties of a Series of Thienylcarbazoles

  摘要：

  A series of thienylcarbazoles were synthesized by Suzuki-Miyaura and Ullmann coupling reactions. In these compounds, the 2-thienyl or 2,2'-bithiophen-5-yl group is connected at the N-, 1,8-, 3,6-, 2,7-, 2,7,N-, or 1,8,N-positions of the carbazole ring. The effects of structural variations on their electronic, photophysical, and electrochemical properties were explored by UV-vis and fluorescence spectroscopies, cyclic voltammetry (CV), and DFT calculations in evaluation of their potential as material components. The thienyl substituents at the 2,7-positions in 4, 5, and 10 are responsible for a high degree of pi-conjugation and strong emission with fluorescence quantum yields up to 0.61. The CV on a series of thienylcarbazoles revealed a good electron-donating ability of 3,6-substituted carbazoles 3 and 9. The number of thiophene units was found to affect the extent of pi-conjugation, the resulting HOMO-LUMO gaps, and fluorescence efficiency. The crystal structures of 5 and 9 were also disclosed.

  DOI：

  10.1021/jo202625p
• 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 1,8-dibromo-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

• Synthesis and Characterization of 1,8-Carbazole-based π-Conjugated Copolymer with Zigzagged Conformation for Stable Deep-blue Emission
  作者：Ran-Ran Liu、Zong-Qiong Lin、Nai-En Shi、Jian-Feng Zhao、Xiao-Ya Hou、Yan Qian、Ling-Hai Xie、Wei Huang

  DOI：10.1246/cl.2010.522

  日期：2010.5.5

  1,8-Dibromocarbazole was employed to construct zigzagged conformation via the Suzuki-type cross-coupling polycondensation. Model copolymer, poly(Cz1,8-co-F), showed deep-blue 420 nm emission in thi...

  1,8-二溴咔唑用于通过铃木型交叉偶联缩聚来构建锯齿形构象。模型共聚物，poly(Cz1,8-co-F)，显示出深蓝色的 420 nm 发射...
• Synthesis and Electronic, Photophysical, and Electrochemical Properties of a Series of Thienylcarbazoles
  作者：Shin-ichiro Kato、Satoru Shimizu、Hiroaki Taguchi、Atsushi Kobayashi、Seiji Tobita、Yosuke Nakamura

  DOI：10.1021/jo202625p

  日期：2012.4.6

  A series of thienylcarbazoles were synthesized by Suzuki-Miyaura and Ullmann coupling reactions. In these compounds, the 2-thienyl or 2,2'-bithiophen-5-yl group is connected at the N-, 1,8-, 3,6-, 2,7-, 2,7,N-, or 1,8,N-positions of the carbazole ring. The effects of structural variations on their electronic, photophysical, and electrochemical properties were explored by UV-vis and fluorescence spectroscopies, cyclic voltammetry (CV), and DFT calculations in evaluation of their potential as material components. The thienyl substituents at the 2,7-positions in 4, 5, and 10 are responsible for a high degree of pi-conjugation and strong emission with fluorescence quantum yields up to 0.61. The CV on a series of thienylcarbazoles revealed a good electron-donating ability of 3,6-substituted carbazoles 3 and 9. The number of thiophene units was found to affect the extent of pi-conjugation, the resulting HOMO-LUMO gaps, and fluorescence efficiency. The crystal structures of 5 and 9 were also disclosed.
• 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.