N-phenyl-N-(4-(thiazol-2-yl)phenyl)benzenamine | 1372541-00-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-phenyl-N-(4-(thiazol-2-yl)phenyl)benzenamine
• 英文别名: N,N-diphenyl-4-(thiazol-2-yl)aniline；N,N-diphenyl-4-(1,3-thiazol-2-yl)aniline
• CAS: 1372541-00-8
• 化学式: C₂₁H₁₆N₂S
• 分子量: 328.437
• InChiKey: GPLLDAVTGOFDDA-UHFFFAOYSA-N

物化性质

• 沸点：
  495.4±47.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-phenyl-N-(4-(thiazol-2-yl)phenyl)benzenamine 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(N-phenyl-N-(4-(thiazol-2-yl)phenyl)benzenamine)]⁺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：

  4-溴三苯胺 在 盐酸 、 四(三苯基膦)钯 、 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 生成 N-phenyl-N-(4-(thiazol-2-yl)phenyl)benzenamine
  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

• Palladium-catalyzed ligand-free and aqueous Suzuki reaction for the construction of (hetero)aryl-substituted triphenylamine derivatives
  作者：Chun Liu、Xiaofeng Rao、Xinlong Song、Jieshan Qiu、Zilin Jin

  DOI：10.1039/c2ra22275b

  日期：——

  This paper reports an efficient synthesis of triphenylamine (TPA) derivatives via a palladium-catalyzed Suzuki reaction of (hetero)aryl halides with 4-(diphenylamino)phenylboronic acid (DPBA) in aqueous ethanol under aerobic and ligand-free conditions. Heteroaryl halides, namely pyridyl bromides, quinolyl bromides, pyrimidinyl bromides, 2-chloropyrazine and sulfur-containing heteroaryl bromides, could

  本文报告了一个有效的综合 三苯胺（TPA）衍生物通过（杂）芳基卤化物与4-（二苯氨基）苯基硼酸（DPBA）水溶液乙醇在无氧和无配体的条件下。杂芳基卤化物，即吡啶基溴化物，喹啉基溴化物，嘧啶基溴化物，2-氯吡嗪含硫杂芳基溴化物可以与DPBA平稳反应，在温和条件下收率好至极好。此外，芳基溴化物也成功地用于与DPBA的交叉偶联中，并在室温下以高收率提供了产品。的交叉耦合4-溴苄腈与DPBA一起使用，在2分钟内以定量收率得到了所需的产物，导致TOF高达5820 h -1。
• Thiazole-based metallophosphors of iridium with balanced carrier injection/transporting features and their two-colour WOLEDs fabricated by both vacuum deposition and solution processing-vacuum deposition hybrid strategy
  作者：Xiaolong Yang、Yongbiao Zhao、Xinwen Zhang、Rui Li、Jingshuang Dang、Yan Li、Guijiang Zhou、Zhaoxin Wu、Dongge Ma、Wai-Yeung Wong、Xiang Zhao、Aimin Ren、Lixiang Wang、Xun Hou

  DOI：10.1039/c2jm14712b

  日期：——

  New phosphorescent iridium(III) cyclometallated complexes bearing thiazole-based ligands (IrTZ1 and IrTZ2) have been developed. The functionalized organic ligands derived by combining the thiazolyl moiety and triphenylamino group have conferred not only favorable hole-injection/hole-transporting (HI/HT) features but also more balanced charge carrier injection/transporting traits to the as-prepared iridium(III) metallophosphors. Owing to the unique electronic structures afforded by the ligand, the orange organic light-emitting devices (OLEDs) made from IrTZ1 can furnish peak external quantum efficiency (ηext) of 14.82%, luminance efficiency (ηL) of 39.97 cd A−1 and power efficiency (ηp) of 34.95 lm W−1. Inspired by its outstanding electroluminescence (EL) performance, the orange IrTZ1 phosphor complemented with a blue phosphor FIrpic was employed to fabricate highly efficient white organic light-emitting devices (WOLEDs) with a single emission layer. Despite their simple device configuration, the optimized WOLEDs can still maintain decent electroluminescence (EL) ability with ηext of 7.20%, ηL of 18.07 cd A−1 and ηp of 19.57 lm W−1. With the aim to simplify the fabrication process of multi-layered WOLEDs, two-component WOLEDs were obtained through a novel solution processing–vacuum deposition hybrid method with the doped blue fluorescent emission layer deposited by a solution process and the orange phosphorescent emission layer made by vacuum deposition. The WOLEDs prepared using such exploratory approach can show an attractive EL performance with ηext of 9.06%, ηL of 22.72 cd A−1 and ηp of 17.28 lm W−1. All these data have indicated not only the great potential of the orange phosphor in monochromatic and white OLEDs, but also the importance of the hybrid method for simplifying WOLED fabrication.

  新型荧光发光的铱(III)环金属化络合物，基于噻唑配体（IrTZ1 和 IrTZ2）已被研发。通过结合噻唑基和三苯胺基团获得的功能化有机配体，不仅赋予了所制备的铱(III)金属磷光体良好的孔注入/孔输运（HI/HT）特性，还使其在电荷载流子注入/输运方面更加平衡。由于配体所赋予的独特电子结构，采用 IrTZ1 制成的橙色有机发光二极管（OLED）可达到14.82%的峰外量子效率（ηext），39.97 cd A−1的亮度效率（ηL）和34.95 lm W−1的功率效率（ηp）。受到其优异电致发光（EL）性能的启发，橙色 IrTZ1 磷光体与蓝色磷光体 FIrpic 结合，被用于制造具有单发射层的高效白色有机发光二极管（WOLED）。尽管其器件结构简单，但优化后的 WOLED 仍可保持不错的电致发光（EL）能力，ηext 为7.20%，ηL 为18.07 cd A−1，ηp 为19.57 lm W−1。为了简化多层 WOLED 的制造过程，通过一种新颖的溶液处理—真空沉积混合方法获得了双组分 WOLED，其中掺杂的蓝色荧光发射层通过溶液工艺沉积，橙色磷光发射层则采用真空沉积制作。采用这种探索性方法制备的 WOLED 显示了吸引人的 EL 性能，ηext 为9.06%，ηL 为22.72 cd A−1，ηp 为17.28 lm W−1。所有这些数据不仅表明了橙色磷光体在单色和白色 OLED 中的巨大潜力，还强调了混合方法在简化 WOLED 制造过程中的重要性。