1,3-bis(4-bromophenyl)azulene | 862421-94-1

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 1,3-bis(4-bromophenyl)azulene
• 英文别名: 1,3-Bis(4-bromophenyl)azulene
• CAS: 862421-94-1
• 化学式: C₂₂H₁₄Br₂
• 分子量: 438.161
• InChiKey: XHEMAMXSFJOVMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,3-bis(4-bromophenyl)azulene 、 二苯胺 在 palladium diacetate sodium t-butanolate 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 甲苯 为溶剂， 以85%的产率得到1,3-bis[4-(N,N-diphenylamino)phenyl]azulene
  参考文献：
  名称：

  Application ofN,N,N′,N′-Tetrasubstituted 1,3-Bis(4-aminophenyl)azulenes to Hole-injecting Materials for Durable Organic EL Devices without Color Fade

  摘要：

  1,3-双（氨基苯基）苊的名称由1,3-二卤苊通过两步合成而来，包括与4-溴苯硼酸的铃木交叉偶联以及随后的钯催化胺化。它们的HOMO能级估计与广泛使用的空穴注入（HI）材料铜酞菁相当。作为非氰基和非多胺物质，这些二胺在有机电致发光（EL）器件中HL材料的应用也得到了研究。

  DOI：

  10.1246/cl.2005.754
• 作为产物：
  描述：

  1,3-二碘甘菊蓝 、 4-溴苯硼酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 以53%的产率得到1,3-bis(4-bromophenyl)azulene
  参考文献：
  名称：

  Application ofN,N,N′,N′-Tetrasubstituted 1,3-Bis(4-aminophenyl)azulenes to Hole-injecting Materials for Durable Organic EL Devices without Color Fade

  摘要：

  1,3-双（氨基苯基）苊的名称由1,3-二卤苊通过两步合成而来，包括与4-溴苯硼酸的铃木交叉偶联以及随后的钯催化胺化。它们的HOMO能级估计与广泛使用的空穴注入（HI）材料铜酞菁相当。作为非氰基和非多胺物质，这些二胺在有机电致发光（EL）器件中HL材料的应用也得到了研究。

  DOI：

  10.1246/cl.2005.754

文献信息

• Application of<i>N</i>,<i>N</i>,<i>N</i>′,<i>N</i>′-Tetrasubstituted 1,3-Bis(4-aminophenyl)azulenes to Hole-injecting Materials for Durable Organic EL Devices without Color Fade
  作者：Mitsunori Oda、Nguyen Chung Thanh、Masamichi Ikai、Takanori Kajioka、Hisayoshi Fujikawa、Yasunori Taga、Satoru Ogawa、Hiroko Shimada、Shigeyasu Kuroda

  DOI：10.1246/cl.2005.754

  日期：2005.6

  The title 1,3-bis(aminophenyl)azulenes were synthesized from 1,3-dihaloazulene in two steps involving the Suzuki cross-coupling with 4-bromophenylboronic acid and subsequent Pd-catalyzed amination. Their HOMO energy levels were estimated to be comparable to that of the widely used hole-injecting (HI) material, copper phthalocyanine. The application of these diamines to HL materials in organic electroluminescent (EL) devices was also studied as non-cyanine and non-polyamine substance.

  1,3-双（氨基苯基）苊的名称由1,3-二卤苊通过两步合成而来，包括与4-溴苯硼酸的铃木交叉偶联以及随后的钯催化胺化。它们的HOMO能级估计与广泛使用的空穴注入（HI）材料铜酞菁相当。作为非氰基和非多胺物质，这些二胺在有机电致发光（EL）器件中HL材料的应用也得到了研究。
• Synthesis of N,N,N′,N′-tetrasubstituted 1,3-bis(4-aminophenyl)azulenes and their application to a hole-injecting material in organic electroluminescent devices
  作者：Nguyen Chung Thanh、Masamichi Ikai、Takanori Kajioka、Hisayoshi Fujikawa、Yasunori Taga、Yanmei Zhang、Satoshi Ogawa、Hiroko Shimada、Yosuke Miyahara、Shigeyasu Kuroda、Mitsunori Oda

  DOI：10.1016/j.tet.2006.09.025

  日期：2006.11

  After a preliminary search of the reaction conditions for the Suzuki-Miyaura cross-coupling of haloazulenes with arylboronic acids, the title compounds were synthesized either by the direct coupling reaction between 1,3-dihaloazulene and the corresponding N,N-disubstituted 4-aminophenylboronic acids or by a two-step sequence involving the cross-coupling with 4-bromophenylboronic acid and subsequent Pd-catalyzed amination. Application of the title diamines to a hole-injecting material in organic electroluminescent devices was carried out to provide their prominent characteristics as a novel durable, non-cyanine and non-polyamine substance without color fade. The diamine derivatives, extended by an ethynyl unit between the azulenyl core and the 4-aminophenyl moiety, were also synthesized and found, unfortunately, unsuitable for vacuum deposition in preparing a multilayer composite. (c) 2006 Elsevier Ltd. All rights reserved.