9-ethyl-3,6-di(thiophen-2-yl)-9H-carbazole

• 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-ethyl-3,6-di(thiophen-2-yl)-9H-carbazole
• 英文别名: 9-ethyl-3,6-di-2-thienyl-9H-carbazole；3,6-bis(2-thienyl)-N-ethyl carbazole；9-ethyl-3,6-dithiophen-2-ylcarbazole
• 化学式: C₂₂H₁₇NS₂
• 分子量: 359.516
• InChiKey: NSCBRSHDANBZSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  61.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-ethyl-3,6-di(thiophen-2-yl)-9H-carbazole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以96%的产率得到
  参考文献：
  名称：

  Systematic Structure–Property Investigations on a Series of Alternating Carbazole–Thiophene Oligomers

  摘要：

  A series of alternating carbazole-thiophene oligomers, namely 2,7-linked carbazole-thiophene oligomers 1, 3, 5, 7, and 9 and 3,6-linked ones 2, 4, 6, 8, and 10, in which the molecular length was systematically elongated, were synthesized by Suzuki-Miyaura coupling reactions. The effects of the conjugation connectivity between the carbazole and thiophene moieties and the molecular length on the electronic, photophysical, and electrochemical properties of 1-10 were comprehensively investigated. In the present oligomer architectures, the connection with thiophene at the 2,7-positions of carbazole ensures pi-conjugation to a high extent and high fluorescence quantum yields, while that at the 3,6-positions enhances the donor ability. The increase in the molecular length of the 2,7-linked oligomers effectively extends pi-conjugation. The relationship between structural variations and photophysical properties was examined by fluorescence lifetime measurements in detail. The X-ray crystal structure of 6 was also disclosed.

  DOI：

  10.1021/jo402416f
• 作为产物：
  描述：

  N-乙基咔唑 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 、 溴 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 反应 0.33h， 生成 9-ethyl-3,6-di(thiophen-2-yl)-9H-carbazole
  参考文献：
  名称：

  通过镍催化的交叉偶联方便地合成3,6-取代的咔唑

  摘要：

  经由镍与格氏试剂的偶联（Corriu-Kumada偶联），由相应的3,6-二溴咔唑高产率地制备3-位和6-位烷基，乙烯基和芳基取代的咔唑。

  DOI：

  10.1016/s0040-4020(98)00786-8

文献信息

• Synthesis, characterization and electroluminescence of carbazole-benzimidazole hybrids with thiophene/phenyl linker
  作者：Durai Karthik、K.R. Justin Thomas、Jwo-Huei Jou、Yu-Lin Chen

  DOI：10.1016/j.dyepig.2016.05.046

  日期：2016.10

  electrochemical, thermal and electroluminescence properties. The thiophene containing dyes showed red-shifted absorption and emission profiles than that of the phenyl analogs due to effective electronic delocalization in the former. Also, the thiophene-based dyes exhibited low oxidation potentials than that of the phenyl analogs attributable to electron richness. Electroluminescence devices were fabricated

  通过使用噻吩或苯基间隔基将它们束缚在一起，合成了包含咔唑和苯并咪唑发色团的新型有机发光材料。探索了3,6-和2,7-二取代。通过光物理，电化学，热和电致发光特性分析了新材料的功能特性。由于在前者中有效的电子离域作用，因此含噻吩的染料比苯基类似物显示出红移的吸收和发射曲线。而且，基于噻吩的染料比由于电子富集的苯基类似物显示出低的氧化电位。使用这些染料作为多层构造的发光层或掺杂剂来制造电致发光器件。包含噻吩基染料的器件在纯净器件中由于能级的良好对齐而显示出较低的开启电压，从而促进了平衡的电荷传输。基于噻吩的染料在该系列中表现出更好的性能，外部量子效率高达1.5％。
• Easy accessible blue luminescent carbazole-based materials for organic light-emitting diodes
  作者：Marta Reig、Cristian Gozálvez、Roger Bujaldón、Gintautas Bagdziunas、Khrystyna Ivaniuk、Nataliya Kostiv、Dmytro Volyniuk、Juozas V. Grazulevicius、Dolores Velasco

  DOI：10.1016/j.dyepig.2016.09.062

  日期：2017.2

  The thermal, optical, electrochemical and charge transport properties of a series of nine straightforward carbazole-based compounds have been analysed and interpreted according to their molecular structure by means of the X-ray analysis of single crystals. A non-doped OLED device with low turn-on voltage and maximum luminance up to 1.4 x 10(4) cd m(-2) was achieved. DFT calculations have been performed to explain the high efficiency of radiative exciton production. (C) 2016 Elsevier Ltd. All rights reserved.
• A convenient synthesis of 3,6-substituted carbazoles via nickel catalyzed cross-coupling
  作者：Minnie Park、Jason R. Buck、Carmelo J. Rizzo

  DOI：10.1016/s0040-4020(98)00786-8

  日期：1998.10

  Alkyl, vinyl and aryl substituted carbazoles at the 3- and 6-positions are prepared in high yield from the corresponding 3,6-dibromocarbazole via nickel catalyzed coupling with Grignard reagents (Corriu-Kumada coupling).

  经由镍与格氏试剂的偶联（Corriu-Kumada偶联），由相应的3,6-二溴咔唑高产率地制备3-位和6-位烷基，乙烯基和芳基取代的咔唑。
• Systematic Structure–Property Investigations on a Series of Alternating Carbazole–Thiophene Oligomers
  作者：Shin-ichiro Kato、Satoru Shimizu、Atsushi Kobayashi、Toshitada Yoshihara、Seiji Tobita、Yosuke Nakamura

  DOI：10.1021/jo402416f

  日期：2014.1.17

  A series of alternating carbazole-thiophene oligomers, namely 2,7-linked carbazole-thiophene oligomers 1, 3, 5, 7, and 9 and 3,6-linked ones 2, 4, 6, 8, and 10, in which the molecular length was systematically elongated, were synthesized by Suzuki-Miyaura coupling reactions. The effects of the conjugation connectivity between the carbazole and thiophene moieties and the molecular length on the electronic, photophysical, and electrochemical properties of 1-10 were comprehensively investigated. In the present oligomer architectures, the connection with thiophene at the 2,7-positions of carbazole ensures pi-conjugation to a high extent and high fluorescence quantum yields, while that at the 3,6-positions enhances the donor ability. The increase in the molecular length of the 2,7-linked oligomers effectively extends pi-conjugation. The relationship between structural variations and photophysical properties was examined by fluorescence lifetime measurements in detail. The X-ray crystal structure of 6 was also disclosed.