N,N',N'',N'''-tetramethyl-1,5,12,16-tetraaza[5.5]paracyclophane

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N',N'',N'''-tetramethyl-1,5,12,16-tetraaza[5.5]paracyclophane
• 英文别名: 2,6,11,15-Tetramethyl-2,6,11,15-tetrazatricyclo[14.2.2.27,10]docosa-1(19),7,9,16(20),17,21-hexaene
• 化学式: C₂₂H₃₂N₄
• 分子量: 352.523
• InChiKey: AJNQTKOUDFQIGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  13
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N',N'',N'''-tetramethyl-1,5,12,16-tetraaza[5.5]paracyclophane 在 六氟锑酸亚硝 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Solution and Solid-State Studies of Doubly Trimethylene-Bridged Tetraalkyl p-Phenylenediamine Diradical Dication Conformations

  摘要：

  X-ray crystallographic structures are reported for 1(Me)(2+)(SbCl6-)(2)center dot 2CH(3)CN, 2(Et)(2+) (SbF6-)(2)center dot 2CH(3)CN center dot 2CH(2)Cl(2), and 1(iPr)(2+)(SbF6-)(2), which also contained unresolved solvent and is in a completely different conformation than the methyl- and ethyl-substituted compounds. A quite different structure of 1(Me)(2+)(SbF6-)(2) than that previously published was obtained upon crystallizing it from a mixture rich in monocation. It does not contain close intramolecular PD+,PD+ contacts but has close intermolecular ones. Low temperature NMR spectra of 1(Me)(2+) and 1(Et)(2+) in 2:1 CD3OD/CD3CN showed that both contain three conformations of all-gauche NCCC unit material with close intramolecular PD+,PD+ contacts. In addition to the both PD+ ring syn and anti material that had been seen in the crystal structure of 1(Me)(2+)(SbF6-)(2)center dot 2CH(3)CN published previously, an unsymmetrical conformation having one PD+ ring syn and the other anti (abbreviated uns) was seen, and the relative amounts of these conformations were significantly different for 1(Me)(2+) and 1(Et)(2+). Calculations that correctly obtain the relative amounts of both the methyl- and ethyl-substituted material as well as changes in the optical spectra between 1(Me)(2+) and 1(Et)(2+), which contains much less of the uns conformation, are reported.

  DOI：

  10.1021/ja100322k
• 作为产物：
  描述：

  聚合甲醛 、 1,5,12,16-tetraaza[5,5]paracyclophane 在 sodium tetrahydroborate 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 以40%的产率得到N,N',N'',N'''-tetramethyl-1,5,12,16-tetraaza[5.5]paracyclophane
  参考文献：
  名称：

  Wurster Blue Cyclophanes 的合成及氧化还原行为

  摘要：

  已经合成了由两个对苯二胺 (PPD) 单元组成的两个环芳烃，这些单元通过不同长度的亚甲基链 (1c, n = 3; 2c, n = 5) 连接。环芳 1c 的 PPD 单元通过双电子转移过程氧化，在第一氧化电位下得到 1c2+。相比之下，2c 通过单电子转移过程氧化得到 2c+，然后得到 2c2+。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  DOI：

  10.1002/ejoc.200400289

文献信息

• MULTI-ELECTRON REDOX ACTIVE MOLECULES FOR ENERGY STORAGE APPLICATIONS
  申请人：UChicago Argonne, LLC

  公开号：US20170062862A1

  公开（公告）日：2017-03-02

  A non-aqueous redox flow battery includes a catholyte including a compound of formula (I) or a compound of formula (II): Where X 1 is a moiety of formula I-A or I-B:

  一种非水性氧化还原流电池，包括阴极液，其中包括化合物(I)的化合物或化合物(II)的化合物：其中X1是公式I-A或I-B的基团：
• Multi-electron redox active molecules for energy storage applications
  申请人：UChicago Argonne, LLC

  公开号：US10026984B2

  公开（公告）日：2018-07-17

  A non-aqueous redox flow battery includes a catholyte including a compound of formula (I) or a compound of formula (II): Where X1 is a moiety of formula I-A or I-B:

  非水氧化还原液流电池包括一种阴溶液，其中包括式（I）化合物或式（II）化合物： 其中 X1 是式 I-A 或 I-B 的分子：
• Synthesis and Redox Behavior of Wurster Blue Cyclophanes
  作者：Hiroyuki Takemura、K� Takehara、Masafumi Ata

  DOI：10.1002/ejoc.200400289

  日期：2004.12

  Two cyclophanes composed of two p-phenylenediamine (PPD) units connected by methylene chains of different lengths (1c, n = 3; 2c, n = 5) have been synthesized. The PPD unit of cyclophane 1c was oxidized by a two-electron transfer process to give 1c2+ at the first oxidation potential. In contrast, 2c was oxidized by a one-electron transfer process to give 2c+ and then 2c2+. (© Wiley-VCH Verlag GmbH

  已经合成了由两个对苯二胺 (PPD) 单元组成的两个环芳烃，这些单元通过不同长度的亚甲基链 (1c, n = 3; 2c, n = 5) 连接。环芳 1c 的 PPD 单元通过双电子转移过程氧化，在第一氧化电位下得到 1c2+。相比之下，2c 通过单电子转移过程氧化得到 2c+，然后得到 2c2+。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Solution and Solid-State Studies of Doubly Trimethylene-Bridged Tetraalkyl <i>p</i>-Phenylenediamine Diradical Dication Conformations
  作者：Almaz S. Jalilov、Gaoquan Li、Stephen F. Nelsen、Ilia A. Guzei、Qin Wu

  DOI：10.1021/ja100322k

  日期：2010.5.5

  X-ray crystallographic structures are reported for 1(Me)(2+)(SbCl6-)(2)center dot 2CH(3)CN, 2(Et)(2+) (SbF6-)(2)center dot 2CH(3)CN center dot 2CH(2)Cl(2), and 1(iPr)(2+)(SbF6-)(2), which also contained unresolved solvent and is in a completely different conformation than the methyl- and ethyl-substituted compounds. A quite different structure of 1(Me)(2+)(SbF6-)(2) than that previously published was obtained upon crystallizing it from a mixture rich in monocation. It does not contain close intramolecular PD+,PD+ contacts but has close intermolecular ones. Low temperature NMR spectra of 1(Me)(2+) and 1(Et)(2+) in 2:1 CD3OD/CD3CN showed that both contain three conformations of all-gauche NCCC unit material with close intramolecular PD+,PD+ contacts. In addition to the both PD+ ring syn and anti material that had been seen in the crystal structure of 1(Me)(2+)(SbF6-)(2)center dot 2CH(3)CN published previously, an unsymmetrical conformation having one PD+ ring syn and the other anti (abbreviated uns) was seen, and the relative amounts of these conformations were significantly different for 1(Me)(2+) and 1(Et)(2+). Calculations that correctly obtain the relative amounts of both the methyl- and ethyl-substituted material as well as changes in the optical spectra between 1(Me)(2+) and 1(Et)(2+), which contains much less of the uns conformation, are reported.