3,6-di-(2-thienyl)-9-hexylcarbazole | 1323142-57-9

• 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: 3,6-di-(2-thienyl)-9-hexylcarbazole
• 英文别名: 9-hexyl-3,6-di(thiophen-2-yl)-9H-carbazole；9-Hexyl-3,6-dithiophen-2-ylcarbazole
• CAS: 1323142-57-9
• 化学式: C₂₆H₂₅NS₂
• 分子量: 415.623
• InChiKey: NYWHVQWNKCRLJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  3,6-di-(2-thienyl)-9-hexylcarbazole 在 ammonium acetate 、 三氯氧磷 作用下， 以 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 反应 20.0h， 生成 3,3'-(5,5'-(9-hexyl-9H-carbazole-3,6-diyl)bis(thiophene-5,2-diyl))bis(2-cyanoacrylic acid)
  参考文献：
  名称：

  Synthesis and Photovoltaic Performance of Long Wavelength Absorbing Organic Dyes for Dye-Sensitized Solar Cells

  摘要：

  We prepared novel organic photo-sensitizers based on a carbazole framework containing various acceptors with thiophene bridge units in the chromophore for the application to dye-sensitized solar cell (DSSC). Furthermore, organic dyes without bridge in the chromophore also synthesized to investigate the correlation between conjugation lengths and photon-to-current efficiency (PCE). Compared to non-bridged dyes, the DSSCs device containing multi-anchoring dyes with thiophene bridge exhibited much higher PCEs, resulting from efficient electron extraction pathways, higher molar extinction coefficients, and better light absorption in longer wavelengths.

  DOI：

  10.1080/15421406.2011.601189
• 作为产物：
  描述：

  N-hexylcarbazole 在 N-溴代丁二酰亚胺(NBS) 、 trans-bis(triphenylphosphine)palladium dichloride 作用下， 以 四氢呋喃 、 吡啶 、 邻二氯苯 为溶剂， 反应 6.0h， 生成 3,6-di-(2-thienyl)-9-hexylcarbazole
  参考文献：
  名称：

  基于咔唑和红色吸收性阳离子吲哚的单支和双支有机染料用于p型染料敏化太阳能电池：结合实验和理论研究

  摘要：

  已经为p型染料敏化太阳能电池合成了一系列新颖的单支和双支咔唑基红色吸收阳离子染料，不含（CSI和CDI），不含（CST和CDT）噻吩间隔基（p-DSSC）。吸收红光的阳离子受体/噻吩间隔基的引入导致吸收最大值从CSI的600 nm起始到CDT的800 nm扩展和红移，并提高了摩尔吸收率。双支/噻吩间隔基的引入降低了CDI，CST和CDT的最低空位分子轨道（LUMO）水平，使其电势比CSI更强。其中，双支CDI的转化效率最高，为0.112％。此外，在相似的制造条件下测得的所有染料均优于标准C343染料（0.062％）。尽管由于噻吩间隔基的引入导致光伏性能下降，但总体而言，与单支链染料的SC和V OC值相比。电化学阻抗谱分析表明，双支化染料比单支化染料具有更低的电荷转移电阻和更长的空穴寿命。进行密度泛函理论（DFT）和与时间有关的DFT计算，以从理论上表征合成染料的光学和电化学性质。

  DOI：

  10.1016/j.dyepig.2017.09.042

文献信息

• Two-photon absorption dyes with thiophene as π electron bridge: Synthesis, photophysical properties and optical data storage
  作者：Hongping Zhou、Feixia Zhou、Shiya Tang、Peng Wu、Yixin Chen、Yulong Tu、Jieying Wu、Yupeng Tian

  DOI：10.1016/j.dyepig.2011.06.028

  日期：2012.1

  Four novel dyes are prepared by thiophene as pi bridge between carbazole central core and other terminal groups by Suzuki and Heck coupling reactions. These dyes are fully characterized by IR, H-1 NMR, C-13 NMR, MS and elemental analysis. Linear absorption, single- and two-photon excited fluorescence in various solvents are experimentally investigated. The calculated two-photon absorption cross sections of 9-Hexyl-3,6-di((5-phenyl)-2-thienyl)carbazole (1), 9-Hexyl-3,6-di((5-thienyl)-2-thienyl)carbazole (2), 9-Hexyl-3,6-di((5-p-vinylpyridyl)-2-thienyl)-carbazole (3) and 9-Hexyl-3,6-di-((5-o-vinylpyridyl)-2-thienyl) carbazole (4) for the lowest excited state are 537.84, 550.76, 1292.95 and 1340.40 x 10(-50) cm(4) s photon(-1), respectively. Calculated and experimental data have shown that thiophene as pi electron bridge improves the two-photon absorption cross sections greatly. Two-photon optical data recording experiments have been carried out at 820 nm laser radiation. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.