bis(4-(imidazol-1-yl)phenyl)diazene | 1263305-79-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: bis(4-(imidazol-1-yl)phenyl)diazene
• 英文别名: bis(4-imidazol-1-yl-phenyl)diazene
• CAS: 1263305-79-8
• 化学式: C₁₈H₁₄N₆
• 分子量: 314.349
• InChiKey: WHGKHODHZDVSAA-QURGRASLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.36
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  bis(4-(imidazol-1-yl)phenyl)diazene 、 Mg(tn-OEP) 以 二氯甲烷 为溶剂， 反应 0.5h， 以82%的产率得到[Mg(meso-tetranitrooctaethylporphyrin(-2H))(NC₃H₃NC₆H₄NNC₆H₄NC₃H₃N)]
  参考文献：
  名称：

  通过双齿轴向配体自组装形成非常稳定的镁卟啉聚合物：合成，结构，表面形态和桥联配体的影响。

  摘要：

  由几个双齿轴向配体介导的一系列四硝基八乙基卟啉镁的超分子结构已经以优异的产率合成并进行了结构表征。在本研究中，使用了六个链长增加的共轭轴向配体，其中连续离子之间的Mg···Mg非键合距离也从0.73 nm增加到2.70 nm。据我们所知，这是第一个报道，其中很容易在一个锅中合成了具有如此长间隔基的稳定的金属卟啉聚合物。在六配位配合物的X射线结构中观察到线性一维（1D）聚合物链，其中卟啉单元彼此平行排列，具有所谓的“烤肉串”状结构，以保持错位堆积的重叠。然而，经过最佳的Mg···Mg非结合距离后，这些1D链不再继续，而是形成具有“轮轴”结构的五配位卟啉二聚体，然后通过π-π相互作用在垂直方向上自聚集。这种方式可以更有效地填充由大型桥联配体产生的空间，从而形成球形结构。还研究了溶液中分子的结构及其在高度有序热解石墨（HOPG）上的表面图案。相反，它们形成类似“轮轴”构架的五配位卟啉二聚体，然后

  DOI：

  10.1021/ic300826p
• 作为产物：
  描述：

  1-(4-硝基苯)-1H-咪唑 在 sodium hydroxide 、 锌 作用下， 以 水 、 异丙醇 为溶剂， 反应 24.0h， 以70%的产率得到bis(4-(imidazol-1-yl)phenyl)diazene
  参考文献：
  名称：

  A Dynamic Open Framework Exhibiting Guest- and/or Temperature-Induced Bicycle-Pedal Motion in Single-Crystal to Single-Crystal Transformation

  摘要：

  A ligand bis(4-imidazol-1-yl-phenyl)diazene (azim) incorporating an azo moiety at the center and two imidazole groups at the terminals forms two coordination polymers {[Co(azim)(2)(DMF)(2)]center dot(ClO4)(2)center dot 2DMF}(n) (1) and {[Cd(azim)(2)-(DMF2]center dot (ClO4)(2)center dot 2DMF}(n) (2) (DMF = NN'-dimethylformamide) at room temperature. Both 1 and 2 are isostructural with rhombic two-dimensional sheets stacking in ABAB... fashion resulting in large voids that contain DMF and ClO4- as guests. In 1, the azo groups and phenyl rings are disordered over two positions and as in usual cases, the pedal motion cannot be discerned. Upon heating, 1 turns amorphous. In the case of 2, however, heat treatment does not lead to loss of crystallinity. Thus, when a crystal of 2 (mother crystal) is heated slowly, it causes substantial movement or escape of both metal-bound and lattice DMF besides movement of ClO4- anions to give daughter crystals 2a, 2b, and 2c without losing crystallinity (single-crystal to single-crystal (SC-SC) transformation). Most interestingly, the X-ray structures of 2 and its daughter products reveal stepwise reversible bicycle-pedal or crankshaft motion of the azo group. When a crystal of 2c is kept in DMF for 10 h, crystal 2' is formed whose structure is similar to that of 2 with slight changes in the bond distances and angles. Also, crystals of 2 are converted to 3 and 4 upon being kept in acetone or DEF (DEF = N, N-diethylformamide), respectively, for 10 h at ambient temperature in SC-SC transformation. In 3, each lattice DMF molecule is replaced by an acetone molecule, leaving the two coordinated DMF molecules intact. However, in 4, all lattice and coordinated DMF molecules are replaced by equal number of DEF molecules. Both in 3 and 4, the azo moieties show bicycle-pedal motion. Thus, bicycle-pedal motion that normally cannot be observed is shown here to be triggered by heat as well as guest molecules in SC-SC fashion.

  DOI：

  10.1021/ic102305v

文献信息

• Helicity-induced two-layered Cd(II) coordination polymers built with different kinked dicarboxylates and an organodiimidazole
  作者：Subhadip Neogi、Manish K. Sharma、Madhab C. Das、Parimal K. Bharadwaj

  DOI：10.1016/j.poly.2009.09.005

  日期：2009.12

  A new ligand bis-(4-imidazol-1-yl-phenyl)-diazene (azim), incorporating an azo moiety at the center and two imidazole groups at the terminals has been designed and synthesized. Under solvothermal conditions, this ligand reacts with Cd(NO3)(2)center dot 6H(2)O and different angular aromatic dicarboxylates to form layered coordination polymers: [Cd(azim)(bcp)](n) (1) and [Cd(azim)(oba)](H2O)}(n) (2) [bcpH(2) = 1,3-bis-(4'-carboxy phenoxy)benzene; oba = 4,4'-oxybis(benzoate)]. Both 1 and 2 have been characterized by single-crystal X-ray diffraction technique, elemental analysis, PXRD and IR spectroscopy. The structure of each polymer looks like 2D grid where two layers are interpenetrated in a "cloth-like" topology. Both the structures contain single- and double-stranded helical coils where the pitches as well as the width are controlled by the carboxylate co-ligands. The hydrogen-bonding interactions between adjacent layers extend these structures to overall 3D supramolecular architectures. (C) 2009 Elsevier Ltd. All rights reserved.