4-nitro-4',4''-dibromotriphenylamine | 144393-34-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-nitro-4',4''-dibromotriphenylamine
• 英文别名: 4-nitrophenyl-bis(4'-bromophenyl)amine；Bis(4 bromophenyl)(4' nitro phenyl)amine；N,N-bis(4-bromophenyl)-4-nitroaniline
• CAS: 144393-34-0
• 化学式: C₁₈H₁₂Br₂N₂O₂
• 分子量: 448.113
• InChiKey: WJPCVWFNWRCBMR-UHFFFAOYSA-N

物化性质

• 熔点：
  221 °C
• 沸点：
  540.2±45.0 °C(Predicted)
• 密度：
  1.692±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-nitro-4',4''-dibromotriphenylamine 在 tin 、 tetrafluoroboric acid 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 8.0h， 生成 4-氟-N,N-二苯基苯胺
  参考文献：
  名称：

  Construction of Electrocatalytic Electrodes Bearing the Triphenylamine Nucleus Covalently Bound to Carbon. A Halogen Dance in Protonated Aminotriphenylamines

  摘要：

  DOI：

  10.1021/ol0603458
• 作为产物：
  描述：

  4-硝基苯基二苯胺 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 以99%的产率得到4-nitro-4',4''-dibromotriphenylamine
  参考文献：
  名称：

  Construction of Electrocatalytic Electrodes Bearing the Triphenylamine Nucleus Covalently Bound to Carbon. A Halogen Dance in Protonated Aminotriphenylamines

  摘要：

  DOI：

  10.1021/ol0603458

文献信息

• Supramolecular Polymerization of Triarylamine-Based Macrocycles into Electroactive Nanotubes
  作者：Flavio Picini、Susanne Schneider、Odile Gavat、Andreas Vargas Jentzsch、Junjun Tan、Mounir Maaloum、Jean-Marc Strub、Shoichi Tokunaga、Jean-Marie Lehn、Emilie Moulin、Nicolas Giuseppone

  DOI：10.1021/jacs.1c00623

  日期：2021.5.5

  This macrocycle is shown to undergo supramolecular polymerization in o-dichlorobenzene, and its nanotubular structure is elucidated by a combination of spectroscopy and microscopy techniques, together with X-ray scattering and molecular modeling. Upon sequential oxidation, a spectroelectrochemical analysis of the supramolecular polymer suggests an extended electronic delocalization of charge carriers

  甲小号6 -对称三芳胺类大环（即，六氮杂[1 6 ]对环芳烷），装饰有六根侧酰胺官能团，是通过会聚和模块化策略合成。该大环显示在邻二氯苯中发生超分子聚合，其纳米管结构通过光谱学和显微镜技术的结合以及 X 射线散射和分子建模来阐明。在连续氧化后，超分子聚合物的光谱电化学分析表明大环内（通过键）和大环之间沿堆叠方向（通过空间）的电荷载流子的扩展电子离域。
• Electron-transfer oxidation of trinitromethanide ion by radical cations
  作者：Lennart Eberson、Finn Radner、Jan Olof Svensson

  DOI：10.1039/c39920001140

  日期：——

  The reaction between tris(4-X-phenyl)aminium ions (X = Br, Cl) and trinitromethanide ion in dichloromethane or acetonitrile takes place by one-electron transfer, eventually leading to nitro derivatives of the triarylamines.

  三（4-X-苯基）铵离子（X = Br，Cl）与二氯甲烷或乙腈中的三硝基甲烷离子之间的反应是通过一电子转移进行的，最终形成三芳基胺的硝基衍生物。
• Flexible electrochromic devices having remarkable color change from golden to green and their application in smart windows and electronic labels
  作者：Xu Guo、Peng Wang、Chao Qian、Chuanyu Jiang、Ping Liu

  DOI：10.1039/d2nj03647a

  日期：——

  study, four viologen derivatives, namely, 1,1′-bis(4-(bis(4-bromophenyl)amino)phenyl)-[4,4′-bipyridine]dihexafluorophosphate (DBrPV), 1-benzyl-1′-(4-(bis(4-bromophenyl)amino)phenyl)-[4,4′-bipyridine]dihexafluorophosphate (Bn-BrPV), 1,1′-bis(4-(3,6-dibromo-9H-carbazol-9-yl)phenyl)-[4,4′-bipyridine]dihexafluorophosphate (DBrCV), and 1-benzyl-1′-(4-(3,6-dibromo-9H-carbazol-9-yl)phenyl)-[4,4′-bipyridine]d

  在这项研究中，四种紫罗碱衍生物，即 1,1'-双(4-(双(4-溴苯基)氨基)苯基)-[4,4'-联吡啶]二六氟磷酸酯 ( DBrPV )、1-benzyl-1' -(4-(双(4-溴苯基)氨基)苯基)-[4,4'-联吡啶]二六氟磷酸盐( Bn-BrPV ), 1,1'-双(4-(3,6-dibromo-9 H -) carbazol-9-yl)phenyl)-[4,4'-bipyridine]dihexafluorophosphate ( DBrCV ), and 1-benzyl-1'-(4-(3,6-dibromo-9 H -carbazol-9-yl)phenyl )-[4,4'-联吡啶]二六氟磷酸盐 ( Bn-BrCV), 被合成。使用四种紫罗碱衍生物作为活性材料制造电致变色器件 (ECD)。ECD的结构是ITO-PET（或ITO-玻璃）/电致变色活性材料/ITO-PET（或ITO-玻璃）。在施加电压下，柔性和刚性
• Two-Photon Fluorescent Holographic Rewritable Micropatterning
  作者：Eléna Ishow、Arnaud Brosseau、Gilles Clavier、Keitaro Nakatani、Robert B. Pansu、Jean-Jacques Vachon、Patrick Tauc、Dominique Chauvat、Cleber R. Mendonça、Erick Piovesan

  DOI：10.1021/ja0735756

  日期：2007.7.1

  Monomeric amorphous systems involving an upper azo-based layer and a lower fluorophore layer have been carefully designed to enable holographic formation of micrometric emissive photopatterns through reversible photoinduced mass migration of azoderivatives. The fluorescent patterns evidenced by NIR biphotonic excitation match the micrometric surface relief. After successful erasure by using a circularly polarized visible light, new patterns can be written again.
• Photochemical Nitration by Tetranitromethane. Part XXXVIII. Nitration of Tris(4-bromophenyl)amine, a Compound Corresponding to a Stable Radical Cation.
  作者：Lennart Eberson、Michael P. Hartshorn、Jan Olof Svensson、Risto Mannonen、Enn Mellikov、Lauri Niinistö、Stenbjörn Styring、Cecilia Tommos、Kurt Warncke、Bryan R. Wood

  DOI：10.3891/acta.chem.scand.51-0279

  日期：——

  The photochemical reaction between tris(4-bromophenyl)amine (TBPA) and tetranitromethane in dichloromethane or acetonitrile gave almost exclusively the nitro-debromination product, 4-nitrophenylbis (4'-bromophenyl) amine (1). In the presence of trifluoroacetic acid, the 2-nitro-substitution product, 4-bromo-2-nitrophenylbis (4'-bromophenyl) amine (3) also appeared, together with further brominated TBPAs (4). Preparative and kinetic studies of the individual reactions involved, viz. the TBPA-NO2, TBPA(.+)-NO2 and TBPA(.+)-trinitromethanide ion reactions, indicated that the simple regiochemistry of the photochemical reaction is due to an addition-elimination mechanism, in which the initial attack of trinitromethanide ion occurs at the carbon ipso to the nitrogen function.