N,N-diphenyl-4-(5-methylpyridinyl-2-yl)aniline | 1263145-40-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-diphenyl-4-(5-methylpyridinyl-2-yl)aniline
• 英文别名: 4-(5-methylpyridin-2-yl)-N,N-diphenylaniline
• CAS: 1263145-40-9
• 化学式: C₂₄H₂₀N₂
• 分子量: 336.436
• InChiKey: GDAJFJJWVBDOPM-UHFFFAOYSA-N

物化性质

• 熔点：
  108-110 °C
• 沸点：
  502.4±38.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-diphenyl-4-(5-methylpyridinyl-2-yl)aniline 在 sodium carbonate 作用下， 以 乙二醇乙醚 、 水 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Novel triphenylamine-based cyclometalated platinum(II) complexes for efficient luminescent oxygen sensing

  摘要：

  Novel triphenylamine-based cyclometalated Pt(II) complexes containing a pyridyl moiety have been synthesized and fully characterized. The cyclometalating ligands were prepared via an efficient palladium-catalyzed ligand-free Suzuki reaction of 4-(diphenylamino)phenylboronic acid with 2-pyridyl bromides under aerobic and aqueous conditions. The photophysical properties of the complexes exhibited that introducing an electron-withdrawing group like trifluoromethyl or cyano group on the 5-position of the pyridine ring affected the LUMO level of the Pt(II)) complex significantly, resulting in a marked decrease in energy gap. Moreover, the complex with a cyano group at the 5-position imparts a substantial red-shift up to 56 nm. The O-2 sensitivity of the complexes was quantitatively evaluated in a polymer film. The results of the O-2-sensing sensitivity of the Pt(II) complexes demonstrated that the complex with a nitrile ligand exhibited the highest sensitivity (K-SV(app) = 0.102 Torr(-1)). The triphenylamine-based cyclometalated Pt(II) complexes are potential candidates for efficient luminescent oxygen sensing. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.09.030
• 作为产物：
  描述：

  2-溴-5-甲基吡啶 、 4-硼酸三苯胺 在 potassium phosphate tribasic heptahydrate 、 palladium diacetate 作用下， 以 水 、 异丙醇 为溶剂， 反应 0.67h， 以93%的产率得到N,N-diphenyl-4-(5-methylpyridinyl-2-yl)aniline
  参考文献：
  名称：

  用于合成 4-芳基取代的三苯胺衍生物的快速、无配体和有氧方案

  摘要：

  描述了通过钯催化的芳基卤化物与 [4-（二苯基氨基）苯基] 硼酸在 iPrOH 水溶液中的有氧 Suzuki 反应合成一系列 4-芳基取代的三苯胺衍生物的快速、方便和无配体的方案. 重要的是，芳基溴化物和杂芳基卤化物在温和条件下都提供了良好到极好的产率。

  DOI：

  10.1002/ejoc.201100072

文献信息

• Very Fast, Ligand-Free and Aerobic Protocol for the Synthesis of 4-Aryl-Substituted Triphenylamine Derivatives
  作者：Chun Liu、Qijian Ni、Jieshan Qiu

  DOI：10.1002/ejoc.201100072

  日期：2011.6

  A fast, convenient and ligand-free protocol for the synthesis of a series of 4-aryl-substituted triphenylamine derivatives by a palladium-catalysed aerobic Suzuki reaction of aryl halides with [4-(diphenylamino)phenyl]boronic acid in aqueous iPrOH is described. Importantly, both aryl bromides and heteroaryl halides afforded good to excellent yields under mild conditions.

  描述了通过钯催化的芳基卤化物与 [4-（二苯基氨基）苯基] 硼酸在 iPrOH 水溶液中的有氧 Suzuki 反应合成一系列 4-芳基取代的三苯胺衍生物的快速、方便和无配体的方案. 重要的是，芳基溴化物和杂芳基卤化物在温和条件下都提供了良好到极好的产率。
• 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。
• 基于吡啶的环金属配体-铂配合物及其制备方法 与应用
  申请人：大连理工大学

  公开号：CN103145763B

  公开（公告）日：2016-06-15

  一种新型环金属配体-铂配合物及其制备方法与应用，其属于电子材料技术领域。这种新型环金属配体-铂配合物通过模版化设计方便易得，在材料中引入三苯胺基、喹啉基或三氟甲基，通过调节氮杂芳环上的取代基可以方便地调节材料的电子结构和空穴注入与传输性能。本发明合成的配合物具有良好的热稳定性和空穴注入与传输性能，在有机电致发光材料、氧传感材料、染料和医药等领域中有着广泛的应用前景，用其制备的氧传感器具有结构简单、成本低、工作可靠等优点，可制成便携式氧传感器推广使用。
• Bis-cyclometalated Ir(III) complexes with a diphenylamino group: design, synthesis, and application in oxygen sensing
  作者：Chun Liu、Hongcui Yu、Xiaofeng Rao、Xin Lv、Zilin Jin、Jieshan Qiu

  DOI：10.1016/j.dyepig.2016.09.022

  日期：2017.1

  oxygen-sensitivity than Ir(ppy)2(acac). It is remarkable that introduction of both diphenylamino and trifluoromethyl groups into the cyclometalating ligand enhances the photostability of the corresponding Ir(III) complexes efficiently. The results reveal that the bulky and electron-donating characteristics of the diphenylamino group enhance the performances of the Ir(III) complexes in oxygen sensing.

  制备了一系列CˆN型双环金属化Ir（III）配合物（Ir1 - Ir4），该配合物在2-苯基吡啶（ppy）苯环的4位具有二苯基氨基。通过与模型配合物Ir（）比较，系统地研究了ppy的吡啶基部分的取代基（-H，-CH 3，-F，-CF 3）对这些Ir（III）配合物的光物理和电化学性质的影响。 ppy）2（acac）。到的Ir（III）络合物（IR1 - IR4）示出与磷光发射最大值在530-558纳米范围内，这是所有红移相对的Ir（ppy）2（ACAC）（λ最大 = 518 nm）。与Ir（ppy）2（acac）相比，这些Ir（III）配合物具有更长的磷光寿命和更好的氧敏感性。值得注意的是，将二苯基氨基和三氟甲基都引入到环金属配体中可以有效提高相应的Ir（III）配合物的光稳定性。结果表明，二苯氨基的庞大和供电子特性增强了Ir（III）配合物在氧传感中的性能。
• Novel triphenylamine-based cyclometalated platinum(II) complexes for efficient luminescent oxygen sensing
  作者：Chun Liu、Xinlong Song、Xiaofeng Rao、Yang Xing、Zhonggang Wang、Jianzhang Zhao、Jieshan Qiu

  DOI：10.1016/j.dyepig.2013.09.030

  日期：2014.2

  Novel triphenylamine-based cyclometalated Pt(II) complexes containing a pyridyl moiety have been synthesized and fully characterized. The cyclometalating ligands were prepared via an efficient palladium-catalyzed ligand-free Suzuki reaction of 4-(diphenylamino)phenylboronic acid with 2-pyridyl bromides under aerobic and aqueous conditions. The photophysical properties of the complexes exhibited that introducing an electron-withdrawing group like trifluoromethyl or cyano group on the 5-position of the pyridine ring affected the LUMO level of the Pt(II)) complex significantly, resulting in a marked decrease in energy gap. Moreover, the complex with a cyano group at the 5-position imparts a substantial red-shift up to 56 nm. The O-2 sensitivity of the complexes was quantitatively evaluated in a polymer film. The results of the O-2-sensing sensitivity of the Pt(II) complexes demonstrated that the complex with a nitrile ligand exhibited the highest sensitivity (K-SV(app) = 0.102 Torr(-1)). The triphenylamine-based cyclometalated Pt(II) complexes are potential candidates for efficient luminescent oxygen sensing. (C) 2013 Elsevier Ltd. All rights reserved.