3-(benzo[d]thiazol-2-yl)-9-butyl-9H-carbazole | 1228794-73-7

• 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-(benzo[d]thiazol-2-yl)-9-butyl-9H-carbazole
• 英文别名: 3-benzothiazolyl-9-butyl-carbazole；2-(9-butyl-9H-carbazol-3-yl)benzo[d]thiazole；3-(Benzothiazol-2-yl)-9-butyl-carbazole；2-(9-butylcarbazol-3-yl)-1,3-benzothiazole
• CAS: 1228794-73-7
• 化学式: C₂₃H₂₀N₂S
• 分子量: 356.491
• InChiKey: ZZVOOMNQJHLBLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(benzo[d]thiazol-2-yl)-9-butyl-9H-carbazole 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 40.0h， 生成 [Ru(4,4′-dicarboxylic acid-2,2′-bipyridine)₂(3-(benzo[d]thiazol-2-yl)-9-butyl-9H-carbazole)]⁺PF₆^-
  参考文献：
  名称：

  Thiocyanate-free ruthenium(II) cyclometalated complexes containing uncommon thiazole and benzothiazole chromophores for dye-sensitized solar cells

  摘要：

  Four novel thiocyanate-free ruthenium(II) complexes based on thiazole and benzothiazole cyclometalating ligands were synthesized, characterized and applied in dye-sensitized solar cells (DSSCs). Their photophysical, electrochemical, thermal and photovoltaic properties have been investigated and the experimental results can be correlated well with the computational results obtained by density functional theory (DFT) calculations. Based on the DFT results, the HOMO of the complexes is localized on the electron-donating carbazole or triphenylamine unit whereas the LUMO mainly lies on 4,4'-dicarboxyl-2,2'-bipyridine. These dyes exhibit good thermal stability with the onset decomposition temperature at 5% weight-loss (T-d) over 360 degrees C. For the DSSC device using the dye with the benzothiazole/carbazole-based cyclometalating ligand, the power conversion efficiency (eta) can reach up to 2.98%, with a short-circuit photocurrent density (J(sc)) of 6.25 mA cm(-2), an open-circuit photovoltage (V-oc) of 0.659 V and a high fill factor (ff) of 0.724 under illumination of an AM 1.5 solar cell simulator. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.04.023
• 作为产物：
  描述：

  N-正丁基咔唑 在 三氯氧磷 作用下， 以 水 为溶剂， 反应 3.0h， 生成 3-(benzo[d]thiazol-2-yl)-9-butyl-9H-carbazole
  参考文献：
  名称：

  Thiocyanate-free ruthenium(II) cyclometalated complexes containing uncommon thiazole and benzothiazole chromophores for dye-sensitized solar cells

  摘要：

  Four novel thiocyanate-free ruthenium(II) complexes based on thiazole and benzothiazole cyclometalating ligands were synthesized, characterized and applied in dye-sensitized solar cells (DSSCs). Their photophysical, electrochemical, thermal and photovoltaic properties have been investigated and the experimental results can be correlated well with the computational results obtained by density functional theory (DFT) calculations. Based on the DFT results, the HOMO of the complexes is localized on the electron-donating carbazole or triphenylamine unit whereas the LUMO mainly lies on 4,4'-dicarboxyl-2,2'-bipyridine. These dyes exhibit good thermal stability with the onset decomposition temperature at 5% weight-loss (T-d) over 360 degrees C. For the DSSC device using the dye with the benzothiazole/carbazole-based cyclometalating ligand, the power conversion efficiency (eta) can reach up to 2.98%, with a short-circuit photocurrent density (J(sc)) of 6.25 mA cm(-2), an open-circuit photovoltage (V-oc) of 0.659 V and a high fill factor (ff) of 0.724 under illumination of an AM 1.5 solar cell simulator. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.04.023

文献信息

• The synthesis and optical properties of benzothiazole-based derivatives with various π-electron donors as novel bipolar fluorescent compounds
  作者：Haiying Wang、Gang Chen、Xiaoping Xu、Hua Chen、Shunjun Ji

  DOI：10.1016/j.dyepig.2010.01.010

  日期：2010.8

  Novel bipolar benzothiazole-based derivatives with various π-electron donors were synthesized and characterized using 1H and 13C NMR and mass spectrometry; their thermal, optical and electrochemical properties were also investigated. Optoelectronic properties are reported and discussed in terms of the distribution of the highest occupied molecular orbital and the lowest unoccupied molecular orbital

  合成了具有各种π电子给体的新型双极苯并噻唑基衍生物，并使用1 H和13 C NMR和质谱进行了表征；还研究了它们的热，光学和电化学性能。根据最高占据的分子轨道的分布和最低的未占据的分子轨道的分布以及给电子部分和受电子部分之间的共轭途径来报道和讨论光电子性质。这些化合物表现出高的荧光量子产率，理想的HOMO水平和高的热稳定性。使用量子化学计算来研究优化的基态几何形状以及化合物的HOMO和LUMO水平的空间分布。
• Thiocyanate-free ruthenium(II) cyclometalated complexes containing uncommon thiazole and benzothiazole chromophores for dye-sensitized solar cells
  作者：Chi-Ho Siu、Cheuk-Lam Ho、Jian He、Tao Chen、Xiaoneng Cui、Jianzhang Zhao、Wai-Yeung Wong

  DOI：10.1016/j.jorganchem.2013.04.023

  日期：2013.12

  Four novel thiocyanate-free ruthenium(II) complexes based on thiazole and benzothiazole cyclometalating ligands were synthesized, characterized and applied in dye-sensitized solar cells (DSSCs). Their photophysical, electrochemical, thermal and photovoltaic properties have been investigated and the experimental results can be correlated well with the computational results obtained by density functional theory (DFT) calculations. Based on the DFT results, the HOMO of the complexes is localized on the electron-donating carbazole or triphenylamine unit whereas the LUMO mainly lies on 4,4'-dicarboxyl-2,2'-bipyridine. These dyes exhibit good thermal stability with the onset decomposition temperature at 5% weight-loss (T-d) over 360 degrees C. For the DSSC device using the dye with the benzothiazole/carbazole-based cyclometalating ligand, the power conversion efficiency (eta) can reach up to 2.98%, with a short-circuit photocurrent density (J(sc)) of 6.25 mA cm(-2), an open-circuit photovoltage (V-oc) of 0.659 V and a high fill factor (ff) of 0.724 under illumination of an AM 1.5 solar cell simulator. (C) 2013 Elsevier B.V. All rights reserved.