N-(4-bromophenyl)-N-(4-n-butylphenyl)benzenamine | 230623-63-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(4-bromophenyl)-N-(4-n-butylphenyl)benzenamine
• 英文别名: N-(4-bromophenyl)-4-butyl-N-phenylaniline
• CAS: 230623-63-9
• 化学式: C₂₂H₂₂BrN
• 分子量: 380.327
• InChiKey: CXMKGAYWTPNOCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(4-bromophenyl)-N-(4-n-butylphenyl)benzenamine 在 咪唑 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 9-borabicyclo[3.3.1]nonane dimer 、 双氧水 、 叔丁基锂 、 sodium ethanolate 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.17h， 生成 4-butyl-N-[4-[6-[tert-butyl(dimethyl)silyl]oxyhexyl]phenyl]-N-[4-[2-(4-hexylthiophen-2-yl)ethenyl]phenyl]aniline
  参考文献：
  名称：

  Synthesis of Functionalized Organic Second-Order Nonlinear Optical Chromophores for Electrooptic Applications

  摘要：

  The design and syntheses of functionalized second-order nonlinear optical chromophores, suitable for covalent incorporation into functionalized high-performance polymers, are described. The chromophores with hydroxy alkyl functionality have diarylamino groups as the donor moiety and a styryl thiophene moiety as the conjugated bridge. The triarylamine parts of the molecules were synthesized using palladium-catalyzed C-N bond forming reactions. The conjugated bridge was assembled using the Wittig reaction. The acceptor groups were installed in the last steps of the syntheses.

  DOI：

  10.1021/jo981707v
• 作为产物：
  描述：

  4-butyl-N,N-diphenylaniline 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以70%的产率得到N-(4-bromophenyl)-N-(4-n-butylphenyl)benzenamine
  参考文献：
  名称：

  Novel green light-emitting polyfluorenes containing dibenzothiophene-S,S-dioxide-arylamine derivatives

  摘要：

  Green light-emitting polyfluorenes were synthesized by Suzuki polycondensation via introducing dibenzothiophene-S,S-dioxide-(di-)tri-phenylamine (G(1) and G(2)) moieties and dibenzothiophene-S,S-dioxide (SO) unit into the polyfluorene backbone, respectively. PF-SO-G copolymers show a high thermal stability and a moderate photoluminescence quantum yield in the range of 20-40%. The lowest unoccupied molecular orbital (LUMO) levels reduce with increasing the content of SO unit in the polymers. The efficient energy transfer from fluorene segment to G(1) or G(2) unit occurred in the PL process, and the EL emission peaked at about 510 nm was exclusively from G(1) or G(2) unit. Incorporating SO unit into the polymer backbone makes the device performances improved. The maximal luminous efficiency of 9.0 cd A(-1) with the CIE coordinates of (0.27, 0.56) was obtained for PF-SO15-G(2)5 based on a single-layered device of ITO/PEDOT:PSS/polymer/CsF/Al. And the polymers (PF-SO15-G5)s exhibited a dramatic LE stability at high current densities, even though at the current density of 200 mA cm(-2), the luminous efficiencies only dropped 10%. SO unit lowers the LUMO level, balances the injection and transportation of both electron and hole in the polymers, and therefore improves the device performances. The hole- and electron-only devices show that the hole and electron flux are well balanced, which demonstrates that (PF-SO15-G5)s are bipolar polymers with a balanced charge carrier transport. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2012.05.011

文献信息

• Novel green light-emitting polyfluorenes containing dibenzothiophene-S,S-dioxide-arylamine derivatives
  作者：Huiping Xiao、Lei Yu、Yanhu Li、Wen Yang、Bin Zhang、Wei Yang、Hongbin Wu、Yong Cao

  DOI：10.1016/j.polymer.2012.05.011

  日期：2012.6

  Green light-emitting polyfluorenes were synthesized by Suzuki polycondensation via introducing dibenzothiophene-S,S-dioxide-(di-)tri-phenylamine (G(1) and G(2)) moieties and dibenzothiophene-S,S-dioxide (SO) unit into the polyfluorene backbone, respectively. PF-SO-G copolymers show a high thermal stability and a moderate photoluminescence quantum yield in the range of 20-40%. The lowest unoccupied molecular orbital (LUMO) levels reduce with increasing the content of SO unit in the polymers. The efficient energy transfer from fluorene segment to G(1) or G(2) unit occurred in the PL process, and the EL emission peaked at about 510 nm was exclusively from G(1) or G(2) unit. Incorporating SO unit into the polymer backbone makes the device performances improved. The maximal luminous efficiency of 9.0 cd A(-1) with the CIE coordinates of (0.27, 0.56) was obtained for PF-SO15-G(2)5 based on a single-layered device of ITO/PEDOT:PSS/polymer/CsF/Al. And the polymers (PF-SO15-G5)s exhibited a dramatic LE stability at high current densities, even though at the current density of 200 mA cm(-2), the luminous efficiencies only dropped 10%. SO unit lowers the LUMO level, balances the injection and transportation of both electron and hole in the polymers, and therefore improves the device performances. The hole- and electron-only devices show that the hole and electron flux are well balanced, which demonstrates that (PF-SO15-G5)s are bipolar polymers with a balanced charge carrier transport. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of Functionalized Organic Second-Order Nonlinear Optical Chromophores for Electrooptic Applications
  作者：S. Thayumanavan、Jeffrey Mendez、Seth R. Marder

  DOI：10.1021/jo981707v

  日期：1999.6.1

  The design and syntheses of functionalized second-order nonlinear optical chromophores, suitable for covalent incorporation into functionalized high-performance polymers, are described. The chromophores with hydroxy alkyl functionality have diarylamino groups as the donor moiety and a styryl thiophene moiety as the conjugated bridge. The triarylamine parts of the molecules were synthesized using palladium-catalyzed C-N bond forming reactions. The conjugated bridge was assembled using the Wittig reaction. The acceptor groups were installed in the last steps of the syntheses.