1,4-bis(N,N-di(4-methoxyphenyl)amino)naphthalene

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,4-bis(N,N-di(4-methoxyphenyl)amino)naphthalene
• 英文别名: 1-N,1-N,4-N,4-N-tetrakis(4-methoxyphenyl)naphthalene-1,4-diamine
• 化学式: C₃₈H₃₄N₂O₄
• 分子量: 582.699
• InChiKey: VQFXMUKYQCKNGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  1,4-bis(N,N-di(4-methoxyphenyl)amino)naphthalene 、 silver tetrakis([2,2,2-trifluoro-1,1-bis(trifluoromethyl)ethyl]oxy)aluminate 以 二氯甲烷 为溶剂， 以77.4%的产率得到
  参考文献：
  名称：

  锡勒碳氢化合物的氮类似物

  摘要：

  合成并表征了一系列的双[ N，N-二（4-甲氧基苯基）氨基]芳烃指示剂1 2+ – 3 2+。在理论计算的辅助下，通过各种实验研究了它们的电子结构。发现它们是基态的单线态，并且它们的双自由基特性取决于桥连部分。3 2+具有较小的单重态-三重态能隙，并且其热激发的三重态很容易获得。该作品提供了具有明显双自由基特征的锡尔碳氢化合物的氮类似物。

  DOI：

  10.1002/anie.201410256
• 作为产物：
  描述：

  1,4-二溴代萘 、 4,4'-二甲氧基二苯胺 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三叔丁基膦 、 sodium t-butanolate 作用下， 以 正己烷 、 甲苯 为溶剂， 以71%的产率得到1,4-bis(N,N-di(4-methoxyphenyl)amino)naphthalene
  参考文献：
  名称：

  Electronic Coupling in Tetraanisylarylenediamine Mixed-Valence Systems:  The Interplay between Bridge Energy and Geometric Factors

  摘要：

  We have investigated three organic mixed-valence systems that possess nearly identical inter-redox site distances and differ by the nature of the bridging units benzene, naphthalene, and anthracene: the N,N,N',N'-tetra(4-methoxyphenyl)-1,4-phenylenene-diamine radical cation (1(+)), the 1,4-bis(N,N-di(4-methoxyphenyl)-amino)naphthalene radical cation (2(+)), and the 9,10-bis(N,N-di(4-methoxyphenyl)amino)anthracene radical cation (3(+)). The electronic interactions in these systems have been studied by means of gas-phase ultraviolet photoelectron spectroscopy, vis/NIR spectroscopy, and electronic-structure calculations. The experimental and theoretical results concur to indicate that the strength of electronic interaction decreases in the following order of bridging units: benzene > naphthalene > anthracene. This finding contradicts the usual expectation that anthracene is superior to benzene as a driving force for electronic communication. We explain these results in terms of a super-exchange mechanism and its strong dependence on steric interactions.

  DOI：

  10.1021/ja0512172
• 作为试剂：
  描述：

  S-difluoromethyl-S-phenyl-2,4,6-trimethoxyphenylsulfonium tetrafluoroborate 、 在 1,4-bis(N,N-di(4-methoxyphenyl)amino)naphthalene 、 lithium hydroxide 作用下， 以 乙酸乙酯 为溶剂， 以22 %的产率得到4-benzyl-3-(difluoromethyl)-5-fluoro-3,4-dihydroquinoxalin-2(1H)-one
  参考文献：
  名称：

  CN114685384

  摘要：

  公开号：

文献信息

• Nitrogen Analogues of Thiele’s Hydrocarbon
  作者：Yuanting Su、Xingyong Wang、Yuantao Li、You Song、Yunxia Sui、Xinping Wang

  DOI：10.1002/anie.201410256

  日期：2015.1.26

  no]arene dications 12+–32+ have been synthesized and characterized. Their electronic structures were investigated by various experiments assisted by theoretical calculations. It was found that they are singlets in the ground state and that their diradical character is dependent on the bridging moiety. 32+ has a smaller singlet–triplet energy gap and its excited triplet state is thermally readily accessible

  合成并表征了一系列的双[ N，N-二（4-甲氧基苯基）氨基]芳烃指示剂1 2+ – 3 2+。在理论计算的辅助下，通过各种实验研究了它们的电子结构。发现它们是基态的单线态，并且它们的双自由基特性取决于桥连部分。3 2+具有较小的单重态-三重态能隙，并且其热激发的三重态很容易获得。该作品提供了具有明显双自由基特征的锡尔碳氢化合物的氮类似物。
• Electronic Coupling in Tetraanisylarylenediamine Mixed-Valence Systems:  The Interplay between Bridge Energy and Geometric Factors
  作者：Christoph Lambert、Chad Risko、Veaceslav Coropceanu、Jürgen Schelter、Stephan Amthor、Nadine E. Gruhn、Jason C. Durivage、Jean-Luc Brédas

  DOI：10.1021/ja0512172

  日期：2005.6.1

  We have investigated three organic mixed-valence systems that possess nearly identical inter-redox site distances and differ by the nature of the bridging units benzene, naphthalene, and anthracene: the N,N,N',N'-tetra(4-methoxyphenyl)-1,4-phenylenene-diamine radical cation (1(+)), the 1,4-bis(N,N-di(4-methoxyphenyl)-amino)naphthalene radical cation (2(+)), and the 9,10-bis(N,N-di(4-methoxyphenyl)amino)anthracene radical cation (3(+)). The electronic interactions in these systems have been studied by means of gas-phase ultraviolet photoelectron spectroscopy, vis/NIR spectroscopy, and electronic-structure calculations. The experimental and theoretical results concur to indicate that the strength of electronic interaction decreases in the following order of bridging units: benzene > naphthalene > anthracene. This finding contradicts the usual expectation that anthracene is superior to benzene as a driving force for electronic communication. We explain these results in terms of a super-exchange mechanism and its strong dependence on steric interactions.