4,4'-dibromo-4''-(2-ethylhexyl)triphenylamine | 1092939-93-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4,4'-dibromo-4''-(2-ethylhexyl)triphenylamine
• 英文别名: N,N-bis(4-bromophenyl)-4-(2-ethylhexyl)aniline
• CAS: 1092939-93-9
• 化学式: C₂₆H₂₉Br₂N
• 分子量: 515.331
• InChiKey: DRKSXFRKNGJOBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-(2-ethylhexyl)-N,N-diphenylaniline 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以99%的产率得到4,4'-dibromo-4''-(2-ethylhexyl)triphenylamine
  参考文献：
  名称：

  Synthesis of Benzo[1,2-b:4,3-b′]dithiophene/triphenylamine Copolymers: Effects of Substituents on Optical and EL Properties

  摘要：

  通过 Stille 偶联反应合成了苯并[1,2-b:4,3-b′]二噻吩/三苯胺共聚物 P-2eh（无甲基取代基）以及 P-Me 和 P-2Me（三苯胺位点上有甲基取代基）。在基态，P-Me 和 P-2Me 中位于三苯胺 (TPA) 分子上 BDT 单元正交位置的甲基取代基导致聚合物结构扭曲，并明显限制了聚合物骨架的共轭。然而，在激发态下，所有这些共聚物都显示出平面结构，并观察到几乎相同的发射最大值。这一结果表明，在激发态下，聚合物骨架的π-共轭会导致采用更稳定的平面结构，而不是在基态下观察到的扭曲结构。基于 P-Me 和 P-2Me 的器件的最大电致发光效率比 P-2eh 高出约三倍，这是因为共轭共聚物在固态下的π堆积/聚合受到了限制，而且热稳定性和电化学稳定性也得到了改善。

  DOI：

  10.1246/bcsj.81.1322

文献信息

• ORGANIC ELECTRONIC DEVICES AND POLYMERS, INCLUDING PHOTOVOLTAIC CELLS AND DIKETONE-BASED POLYMERS
  申请人：Brown Christopher T.

  公开号：US20110204341A1

  公开（公告）日：2011-08-25

  Polymers which can be used in p-type materials for organic electronic devices and photovoltaic cells. Compounds, monomers, dimers, trimers, and polymers comprising: Good photovoltaic efficiency and lifetime can be achieved. The R group can provide solubility, environmental stability, and fine tuning of spectroscopic and/or electronic properties. Different polymer microstructures can be prepared which encourage multiple band gaps and broad and strong absorptions. The carbonyl can interact with adjacent thiophene rings to provide backbone with rigidity, induce planarity, and reduce and/or eliminate intramolecular chain twisting defects. Polymers comprising benzodithiophene and/or benzothiadiazole structures can show particularly high performance.

  可以用于有机电子器件和光伏电池的p型材料的高分子。化合物，单体，二聚体，三聚体和聚合物包括：可以实现良好的光伏效率和寿命。R基团可以提供可溶性，环境稳定性和光谱和/或电子性质的微调。可以制备不同的高分子微结构，以鼓励多重带隙和广泛而强烈的吸收。羰基可以与相邻的噻吩环相互作用，提供具有刚性的骨架，诱导平面性，并减少和/或消除分子内链扭曲缺陷。包含苯并噻吩和/或苯并噻二唑结构的高分子可以显示出特别高的性能。
• US8968885B2
  申请人：——

  公开号：US8968885B2

  公开（公告）日：2015-03-03
• [EN] ORGANIC ELECTRONIC DEVICES AND POLYMERS, INCLUDING PHOTOVOLTAIC CELLS AND DIKETONE-BASED POLYMERS<br/>[FR] POLYMÈRES ET DISPOSITIFS ORGANIQUES ÉLECTRIQUES, COMPRENANT DES CELLULES PHOTOVOLTAÏQUES ET DES POLYMÈRES À BASE DE DICÉTONE
  申请人：PLEXTRONICS INC

  公开号：WO2011028827A2

  公开（公告）日：2011-03-10

  Polymers which can be used in p-type materials for organic electronic devices and photovoltaic cells. Compounds, monomers, dimers, trimers, and polymers comprising formula (I); Good photovoltaic efficiency and lifetime can be achieved. The R group can provide solubility, environmental stability, and fine tuning of spectroscopic and/or electronic properties. Different polymer microstructures can be prepared which encourage multiple band gaps and broad and strong absorptions. The carbonyl can interact with adjacent thiophene rings to provide backbone with rigidity, induce planarity, and reduce and/or eliminate intramolecular chain twisting defects. Polymers comprising benzodithiophene and/or benzothiadiazole structures can show particularly high performance.
• Synthesis of Benzo[1,2-<i>b</i>:4,3-<i>b</i>′]dithiophene/triphenylamine Copolymers: Effects of Substituents on Optical and EL Properties
  作者：Yosuke Nishide、Hideji Osuga、Kunihiro Iwata、Kazuhiko Tanaka、Hidefumi Sakamoto

  DOI：10.1246/bcsj.81.1322

  日期：2008.10.15

  Benzo[1,2-b:4,3-b′]dithiophene/triphenylamine copolymers P-2eh (with no methyl substituents) and P-Me and P-2Me (with methyl substituents at triphenylamine sites) were synthesized by Stille coupling reactions. In the ground state, the methyl substituents at the ortho positions to the BDT unit on the triphenylamine (TPA) moiety in P-Me and P-2Me caused twisting of the polymer structure and clearly limited conjugation of the polymer backbones. However, in their excited states, all of these copolymers were shown to have planar structures, and almost the same emission maxima were observed. This result indicates that, in the excited states, π-conjugation of the polymer backbone results in the adoption of a more stable planar structure rather than the twisted structure observed in the ground state. The maximum EL efficiencies of devices based on P-Me and P-2Me were about three times higher than that of P-2eh due to restricted π-stacking/aggregation of the conjugated copolymers in the solid state and improvements in thermal and electrochemical stability.

  通过 Stille 偶联反应合成了苯并[1,2-b:4,3-b′]二噻吩/三苯胺共聚物 P-2eh（无甲基取代基）以及 P-Me 和 P-2Me（三苯胺位点上有甲基取代基）。在基态，P-Me 和 P-2Me 中位于三苯胺 (TPA) 分子上 BDT 单元正交位置的甲基取代基导致聚合物结构扭曲，并明显限制了聚合物骨架的共轭。然而，在激发态下，所有这些共聚物都显示出平面结构，并观察到几乎相同的发射最大值。这一结果表明，在激发态下，聚合物骨架的π-共轭会导致采用更稳定的平面结构，而不是在基态下观察到的扭曲结构。基于 P-Me 和 P-2Me 的器件的最大电致发光效率比 P-2eh 高出约三倍，这是因为共轭共聚物在固态下的π堆积/聚合受到了限制，而且热稳定性和电化学稳定性也得到了改善。