(E)-4-((4-nitrophenyl)diazenyl)-N,N-diphenylaniline | 263757-67-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-4-((4-nitrophenyl)diazenyl)-N,N-diphenylaniline
• 英文别名: 4-(diphenylamino)-4'-nitroazobenzene；4-(4-nitrophenylazo)triphenylamine
• CAS: 263757-67-1
• 化学式: C₂₄H₁₈N₄O₂
• 分子量: 394.433
• InChiKey: SEHYCGWJONNDKG-OCEACIFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.48
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.1
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E)-4-((4-nitrophenyl)diazenyl)-N,N-diphenylaniline 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以80%的产率得到4-[bis(4-bromophenyl)amino]-4'-nitroazobenzene
  参考文献：
  名称：

  Versatile Synthesis of Small NLO-Active Molecules Forming Amorphous Materials with Spontaneous Second-Order NLO Response

  摘要：

  A novel synthetic approach to a series of bulky triarylamines substituted by various electron-withdrawing groups and forming amorphous materials is presented. Under vacuum evaporation, thin films with high optical quality are obtained and exhibit spontaneous second-order nonlinear optical activity. This unprecedented result is likely due to subtle balance between strong dipole-dipole interactions and steric crowding causing self-assembly and noncentrosymmetric local ordering, stable up to one year.

  DOI：

  10.1021/ja038207q
• 作为产物：
  描述：

  三苯胺 、 4-nitrobenzenediazonium tetrafluoroborate 在 NaDBS 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 8.0h， 以35%的产率得到(E)-4-((4-nitrophenyl)diazenyl)-N,N-diphenylaniline
  参考文献：
  名称：

  Versatile Synthesis of Small NLO-Active Molecules Forming Amorphous Materials with Spontaneous Second-Order NLO Response

  摘要：

  A novel synthetic approach to a series of bulky triarylamines substituted by various electron-withdrawing groups and forming amorphous materials is presented. Under vacuum evaporation, thin films with high optical quality are obtained and exhibit spontaneous second-order nonlinear optical activity. This unprecedented result is likely due to subtle balance between strong dipole-dipole interactions and steric crowding causing self-assembly and noncentrosymmetric local ordering, stable up to one year.

  DOI：

  10.1021/ja038207q

文献信息

• Effects of terminal electron acceptor strength on film morphology and ternary memory performance of triphenylamine donor based devices
  作者：Hao Zhuang、Qijian Zhang、Yongxiang Zhu、Xufeng Xu、Haifeng Liu、Najun Li、Qingfeng Xu、Hua Li、Jianmei Lu、Lihua Wang

  DOI：10.1039/c3tc30228h

  日期：——

  This study reports the syntheses, photophysical and electrochemical properties and memory characteristics of triphenylamine (TPA) donor based molecules with progressively weaker terminal acceptor strength (i.e., nitro, acetyl and bromine). The influence of the terminal electron acceptor strength on the film morphology and the devices storage performances was investigated. Nonvolatile ternary (“0”, “1” and “2” states) memory devices for high-density data storage could be achieved with a simple ITO/D–A molecule/Al sandwich configuration for TPA-NAP and TPA-AAP. It is noteworthy that the memory device based on TPA-AAP exhibited a better reproducibility and stability with lower operation voltages than that based on TPA-NAP, promising low-power consumption data-storage. These obtained results demonstrate that altering the terminal electron accepting strength in D–A molecules can adjust the film morphology and the device performances for the design of future advanced organic electronic devices.

  本研究报告了末端受体强度逐渐减弱（即硝基、乙酰基和溴）的三苯胺（TPA）供体分子的合成、光物理和电化学性质以及记忆特性。研究了末端电子受体强度对薄膜形貌和器件存储性能的影响。用于高密度数据存储的非易失性三元（“0”、“1”和“2”状态）存储器件可以通过 TPA-NAP 和 TPA-AAP 的简单 ITO/D-A 分子/Al 夹层配置来实现。值得注意的是，基于TPA-AAP的存储器件比基于TPA-NAP的存储器件在更低的工作电压下表现出更好的再现性和稳定性，有望实现低功耗数据存储。这些结果表明，改变 D-A 分子中的末端电子接受强度可以调整薄膜形态和器件性能，用于未来先进有机电子器件的设计。
• Matsui, Masaki; Suzuki, Masayuki; Hayashi, Masahiro, Bulletin of the Chemical Society of Japan, 2003, vol. 76, # 3, p. 607 - 612
  作者：Matsui, Masaki、Suzuki, Masayuki、Hayashi, Masahiro、Funabiki, Kazumasa、Ishigure, Yoshinao、Doke, Yasuo、Shiozaki, Hisayoshi

  DOI：——

  日期：——
• US6288206B1
  申请人：——

  公开号：US6288206B1

  公开（公告）日：2001-09-11
• [EN] CHIRAL POLYMER COMPOSITIONS EXHIBITING NONLINEAR OPTICAL PROPERTIES<br/>[FR] COMPOSITIONS POLYMERES CHIRALES PRESENTANT DES PROPRIETES OPTIQUES NON LINEAIRES
  申请人：MOLECULAR OPTOELECTRONICS CORP

  公开号：WO2000054103A1

  公开（公告）日：2000-09-14

  Chiral organic polymers doped with or appended by nonlinear optical dyes are disclosed. The use of chiral polymers produces a more stable noncentrosymmetric environment for the dye molecules resulting in unexpectedly long relaxation times as compared with previously used organic polymers. In addition, the NLO/chiral polymer materials exhibit high electro-optical coefficients (r33), high nonlinear optical coefficients (d33), improved long-term thermal stability, and at the same time retain the processing advantages associated with organic polymers. Thus, the present NLO/chiral polymer materials are extremely well-suited for use in second-order nonlinear optical and optoelectronics devices.
• Versatile Synthesis of Small NLO-Active Molecules Forming Amorphous Materials with Spontaneous Second-Order NLO Response
  作者：Eléna Ishow、Cyril Bellaïche、Laurent Bouteiller、Keitaro Nakatani、Jacques A. Delaire

  DOI：10.1021/ja038207q

  日期：2003.12.1

  A novel synthetic approach to a series of bulky triarylamines substituted by various electron-withdrawing groups and forming amorphous materials is presented. Under vacuum evaporation, thin films with high optical quality are obtained and exhibit spontaneous second-order nonlinear optical activity. This unprecedented result is likely due to subtle balance between strong dipole-dipole interactions and steric crowding causing self-assembly and noncentrosymmetric local ordering, stable up to one year.