1,5-bis(di-p-methoxyphenylamino)naphthalene

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,5-bis(di-p-methoxyphenylamino)naphthalene
• 英文别名: 1,5-bis(di(4-methoxyphenyl)amino)naphthalene；1-N,1-N,5-N,5-N-tetrakis(4-methoxyphenyl)naphthalene-1,5-diamine
• 化学式: C₃₈H₃₄N₂O₄
• 分子量: 582.699
• InChiKey: QMADKURFKOMKLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲氧苯胺 在 tris-(dibenzylideneacetone)dipalladium(0) 、 palladium diacetate 三叔丁基膦 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 生成 1,5-bis(di-p-methoxyphenylamino)naphthalene
  参考文献：
  名称：

  Synthesis, thermal, electrochemical, and photophysical characterization of 1,5-bis(diarylamino)naphthalene derivatives as potential hole transport OLED materials

  摘要：

  1,5-双(二芳胺基)萘衍生物（1-9），具有作为电致发光器件中孔传输材料潜力，通过钯催化的二芳胺和1,5-二溴萘的偶联反应获得。对这些化合物的热性能、电化学性质和光物理性质进行了研究，并调查了N-芳基取代基对这些性质的影响。这些材料具有玻璃化转变温度（Tg）范围在70-131°C之间，这些值与芳基取代基的身份有关。循环伏安测量表明，这些化合物具有两个可逆氧化过程，并进一步用于通过与二茂铁/二茂铁阳离子对比来估计这些材料的HOMO能级。通过两个氧化电位之间的差异来衡量的分子内电荷迁移显示，化合物1-8具有与间二氨基苯衍生物类似的共轭程度，而9类似于TPD。化合物1-9在蓝绿区域发射，这些材料的光吸收和发射数据可以通过芳基取代基的电子给体性质来解释。将这些数据与电化学确定的HOMO能级相结合，可以估计LUMO能级。关键词：孔传输材料，二氨基萘，热分析，钯催化芳基化。

  DOI：

  10.1139/v05-101

文献信息

• Bis(diphenylamino)naphthalene host materials: careful selection of the substitution pattern for the design of fully solution-processed triple-layered electroluminescent devices
  作者：Frédéric Dumur、Thanh-Tuân Bui、Sébastien Péralta、Marc Lepeltier、Guillaume Wantz、Gjergji Sini、Fabrice Goubard、Didier Gigmes

  DOI：10.1039/c6ra13824a

  日期：——

  Two new triarylamine-based wide bandgap small molecules differing by the position of their substituents were investigated as hosts for solution-processed organic light-emitting diodes (OLEDs).

  两种基于三芳基胺的宽带隙小分子，由于它们取代基的位置不同，被作为溶液加工有机发光二极管（OLEDs）的宿主进行了研究。
• Synthesis, thermal, electrochemical, and photophysical characterization of 1,5-bis(diarylamino)naphthalene derivatives as potential hole transport OLED materials
  作者：Jingning Shan、Glenn PA Yap、Darrin S Richeson

  DOI：10.1139/v05-101

  日期：2005.6.1

  Novel 1,5-bis(diarylamino)naphthalene derivatives (1–9), which have potential as hole-transporting materials for electroluminescent devices, were obtained through palladium-catalyzed coupling of diarylamines and 1,5-dibromonaphthalene. The thermal, electrochemical, and photophysical properties of these compounds were examined and the effects of the N-aryl substituents on these properties were investigated. These materials possess glass transition temperatures (T_g) that range from 70–131 °C and these values are related to the identity of the aryl substituents. Cyclic voltammetric measurements demonstrated that these compounds possess two reversible oxidation processes and were further used to estimate the HOMO energy levels of these materials by comparison with the ferrocene/ferrocenium couple. The intramolecular charge mobility, as gauged by the difference between the two oxidation potentials, indicates that compounds 1–8 have a similar degree of delocalization as meta-diaminobenzene derivatives while that of 9 is similar to TPD. Compounds 1–9 emit in the blue-green region and optical absorption and emission data for these materials can be rationalized in terms of the electronic donating properties of the aryl substituents. This data when combined with the electrochemically determined HOMO energies allowed estimation of the LUMO energy levels.Key words: hole transport materials, diaminonaphthalene, thermal analysis, palladium-catalyzed arylation.

  1,5-双(二芳胺基)萘衍生物（1-9），具有作为电致发光器件中孔传输材料潜力，通过钯催化的二芳胺和1,5-二溴萘的偶联反应获得。对这些化合物的热性能、电化学性质和光物理性质进行了研究，并调查了N-芳基取代基对这些性质的影响。这些材料具有玻璃化转变温度（Tg）范围在70-131°C之间，这些值与芳基取代基的身份有关。循环伏安测量表明，这些化合物具有两个可逆氧化过程，并进一步用于通过与二茂铁/二茂铁阳离子对比来估计这些材料的HOMO能级。通过两个氧化电位之间的差异来衡量的分子内电荷迁移显示，化合物1-8具有与间二氨基苯衍生物类似的共轭程度，而9类似于TPD。化合物1-9在蓝绿区域发射，这些材料的光吸收和发射数据可以通过芳基取代基的电子给体性质来解释。将这些数据与电化学确定的HOMO能级相结合，可以估计LUMO能级。关键词：孔传输材料，二氨基萘，热分析，钯催化芳基化。