bis[4-[N,N-di(4-methoxyphenyl)amino]phenyl]acetylene | 173981-68-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: bis[4-[N,N-di(4-methoxyphenyl)amino]phenyl]acetylene
• 英文别名: 4,4'-tetraanisyltolandiamine；N,N'-[Ethyne-1,2-diyldi(4,1-phenylene)]bis[4-methoxy-N-(4-methoxyphenyl)aniline]；4-[2-[4-(4-methoxy-N-(4-methoxyphenyl)anilino)phenyl]ethynyl]-N,N-bis(4-methoxyphenyl)aniline
• CAS: 173981-68-5
• 化学式: C₄₂H₃₆N₂O₄
• 分子量: 632.759
• InChiKey: OLWOIGFJHFSIAY-UHFFFAOYSA-N

物化性质

• 沸点：
  774.0±60.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  48
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  bis[4-[N,N-di(4-methoxyphenyl)amino]phenyl]acetylene 在 dicobalt octacarbonyl 作用下， 以 1,4-二氧六环 为溶剂， 以80%的产率得到hexakis{4-[bis(p-methyloxyphenyl)amino]phenyl}benzene
  参考文献：
  名称：

  One- and Two-Dimensional Electron Transfer Processes in Triarylamines with Multiple Redox Centers

  摘要：

  DOI：

  10.1002/(sici)1521-3773(19980817)37:15<2107::aid-anie2107>3.0.co;2-h
• 作为产物：
  描述：

  4,4-二甲氧基三苯胺 在 碘 、 [双(三氟乙酰氧基)碘]苯 作用下， 生成 bis[4-[N,N-di(4-methoxyphenyl)amino]phenyl]acetylene
  参考文献：
  名称：

  One- and Two-Dimensional Electron Transfer Processes in Triarylamines with Multiple Redox Centers

  摘要：

  DOI：

  10.1002/(sici)1521-3773(19980817)37:15<2107::aid-anie2107>3.0.co;2-h

文献信息

• A mixed-valence bis(diarylamino)stilbene: crystal structure and comparison of electronic coupling with biphenyl and tolane analogues
  作者：Stephen Barlow、Chad Risko、Veaceslav Coropceanu、Neil M. Tucker、Simon C. Jones、Zerubba Levi、Viktor N. Khrustalev、Mikhail Yu. Antipin、Tiffany L. Kinnibrugh、Tatiana Timofeeva、Seth R. Marder、Jean-Luc Brédas

  DOI：10.1039/b415018j

  日期：——

  The E-4,4′-bis[di(p-anisyl)amino]stilbene cation is a class-III mixed-valence species with electronic coupling comparable to that in its biphenyl-bridged analogue, whereas its tolane-bridged analogue belongs to class II.

  E-4,4'-双[二(对茴香基)氨基]芪阳离子是III类混合价物质，其电子耦合与其联苯桥类似物相当，而其甲苯桥类似物属于第二类。
• Highly Substituted Azulene Dyes as Multifunctional NLO and Electron-Transfer Compounds
  作者：Christoph Lambert、Gilbert Nöll、Manfred Zabel、Frank Hampel、Elmar Schmälzlin、Christoph Bräuchle、Klaus Meerholz

  DOI：10.1002/chem.200304923

  日期：2003.9.5

  substituted azulene derivatives were synthesised by Pd-mediated dimerisation from the corresponding tolan species. One azulene derivative (2) has donor functionalities (dianisylaminophenyl and dianisylamino) in the 1-, 2-, 3- and 6-positions, while the other (1) has donors (dianisylaminophenyl) in the 2- and 6-positions and acceptors (nitrophenyl) in the 1- and 3-positions. Each azulene derivative shows

  通过Pd介导的二聚作用，从相应的tolan物种合成了两个高度取代的azulene衍生物。一种a菁衍生物（2）在1、2、3和6位上具有供体官能团（dianisylaminophenyl和dianisylamino），而另一种（1）在2和6位上具有供体（dianisylaminophenyl）和受体（硝基苯基）位于1和3位。每种a唑衍生物在固态下均表现出很强的键长变化，这是通过X射线晶体分析确定的，并且在其UV / Vis光谱中大约在450-500 nm处具有很强的CT带。1和2的一阶超极化率是通过超瑞利散射测量的，大约是分散红DR1的一阶。两种a烯衍生物均显示出多种氧化过程。通过UV / Vis / NIR光谱电化学研究了1和2的混合价自由基阳离子的分子内绝热ET行为。可以通过广义Mulliken-Hush理论分析1（+）的间隔-CT谱带，该谱带产生光耦合绝热空穴转移的电子耦合V = 1140
• Reaching the 5% theoretical limit of fluorescent OLEDs with push–pull benzophospholes
  作者：Nicolas Ledos、Denis Tondelier、Bernard Geffroy、Denis Jacquemin、Pierre-Antoine Bouit、Muriel Hissler

  DOI：10.1039/d3tc00245d

  日期：——

  thus, the optical properties. Considering the intense fluorescence in the solid state (powder or thin film) and the favorable redox and thermal properties, these compounds were introduced in multilayered organic light emitting devices. All compounds display high efficiency and one compound even exhibits an external quantum efficiency (EQE) of 5%, which represents the theoretical limit of the EQE of

  我们报告了苯并膦氧化物的合成和表征，其特点是 P 原子上有乙氧基取代基，侧苯基上有供电氨基。这些化合物的光学和氧化还原特性通过实验和计算 (TD-DFT) 进行了研究。特别是，我们展示了供体的性质如何允许微调内部电荷转移 (ICT)，从而微调光学特性。考虑到固态（粉末或薄膜）的强烈荧光以及有利的氧化还原和热性能，这些化合物被引入多层有机发光器件中。所有化合物都表现出高效率，一种化合物甚至表现出 5% 的外量子效率 (EQE)，这代表了纯荧光发射体 EQE 的理论极限。
• One- and Two-Dimensional Electron Transfer Processes in Triarylamines with Multiple Redox Centers
  作者：Christoph Lambert、Gilbert Nöll

  DOI：10.1002/(sici)1521-3773(19980817)37:15<2107::aid-anie2107>3.0.co;2-h

  日期：1998.8.17
• Optically and Thermally Induced Electron Transfer Pathways in Hexakis[4-(N,N-diarylamino)phenyl]benzene Derivatives
  作者：Christoph Lambert、Gilbert Nöll

  DOI：10.1002/1521-3765(20020802)8:15<3467::aid-chem3467>3.0.co;2-1

  日期：2002.8.2

  The optically and thermally induced electron transfer pathways of highly symmetrical (D-3) hexaarylbenzene systems with six triarylamine redox sites have been investigated. Owing to slightly different local redox potentials, the radical trication could be selectively generated by electrochemical methods. This trication shows a strong intervalence charge-transfer band in the near infrared (NIR) that was measured by spectroelectrochemistry and analysed using multi-dimensional Mulliken-Hush theory. Quantum chemical AM1 CI calculations indicate that there is no optically induced concerted three-electron transfer that transforms the ground state into a state in which all three positively charged triarylamine moieties change place with their neutral neighbours. The potential energy surface of the ground state was constructed by using quadratic potentials. From this potential surface it is apparent that there is also no thermally allowed concerted three-electron transfer pathway. Instead, three consecutive one-electron transfer steps are necessary for this process.