2-phenylpyrimidine-4,6-dicarbaldehyde bis[N-methyl-N-(pyridin-2-yl)hydrazone] | 915135-35-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-phenylpyrimidine-4,6-dicarbaldehyde bis[N-methyl-N-(pyridin-2-yl)hydrazone]
• CAS: 915135-35-2
• 化学式: C₂₄H₂₂N₈
• 分子量: 422.492
• InChiKey: QICFMEQVAGOTBO-UHFFFAOYSA-N

物化性质

• 沸点：
  560.9±60.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  82.76
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-phenylpyrimidine-4,6-dicarbaldehyde bis[N-methyl-N-(pyridin-2-yl)hydrazone] 、 zinc trifluoromethanesulfonate 以 乙腈 为溶剂， 反应 2.0h， 以100%的产率得到
  参考文献：
  名称：

  Electronic absorption and emission properties of bishydrazone [2 × 2] metallosupramolecular grid-type architectures

  摘要：

  Several ditopic ligands containing two tridentate bishydrazone coordination subunits and their Zn(II) and Cd(II) [2 x 2] grid-type complexes were prepared and their photoluminescent properties studied. A special attention was devoted to the influence of the orientation of the hydrazone group N-N=in the core of the ligands and their complexes. Its reversal from [pyridine=N-N-pyrimidine] (L1) to [pyridinee-N-N=pyrimidine] (L2) has a strong impact on the observed absorption and emission behaviour of particular ligands (L1 and L2) as well as of their [2 x 2] grid assemblies. The further lateral functionalization of the ligands led to different emission quantum yields of the resulting grids, while their emission and absorption spectra varied very little. The simplest derivative L1 turned out to have the best performance with, for its Zn(II) complex, relatively high quantum yield 60%.

  DOI：

  10.1016/j.ica.2019.05.017
• 作为产物：
  描述：

  2-溴吡啶 以 乙醇 为溶剂， 反应 8.0h， 生成 2-phenylpyrimidine-4,6-dicarbaldehyde bis[N-methyl-N-(pyridin-2-yl)hydrazone]
  参考文献：
  名称：

  Electronic absorption and emission properties of bishydrazone [2 × 2] metallosupramolecular grid-type architectures

  摘要：

  Several ditopic ligands containing two tridentate bishydrazone coordination subunits and their Zn(II) and Cd(II) [2 x 2] grid-type complexes were prepared and their photoluminescent properties studied. A special attention was devoted to the influence of the orientation of the hydrazone group N-N=in the core of the ligands and their complexes. Its reversal from [pyridine=N-N-pyrimidine] (L1) to [pyridinee-N-N=pyrimidine] (L2) has a strong impact on the observed absorption and emission behaviour of particular ligands (L1 and L2) as well as of their [2 x 2] grid assemblies. The further lateral functionalization of the ligands led to different emission quantum yields of the resulting grids, while their emission and absorption spectra varied very little. The simplest derivative L1 turned out to have the best performance with, for its Zn(II) complex, relatively high quantum yield 60%.

  DOI：

  10.1016/j.ica.2019.05.017

文献信息

• Self‐Assembly, Structure and Solution Dynamics of Tetranuclear Zn ²⁺ Hydrazone [2×2] Grid‐Type Complexes
  作者：Mihail Barboiu、Mario Ruben、Georges Blasen、Nathalie Kyritsakas、Elizabeth Chacko、Manisha Dutta、Olga Radekovich、Kimberly Lenton、David J. R. Brook、Jean‐Marie Lehn

  DOI：10.1002/ejic.200500963

  日期：2006.2

  π–π stacking between the phenyl ring and the hydrazone units of the perpendicular ligands in the complexes induces a perfect orthogonal arrangement suitable for applications in self-organized metallosupramolecular systems. Zinc complexes provide an opportunity to study the acid–base chemistry without the added effects due to paramagnetism or redox chemistry. The intermediate protonated grids undergo

  我们描述了基于双（腙）嘧啶络合亚基和八面体配位的 [2×2]Zn2+4 网格络合物的自组装过程以及结构和物理化学性质，其中涉及双三齿配体 7-12 Zn2+ 离子。NMR 光谱数据和 X 射线晶体结构结果表明，在溶液和固态中，配合物 13-18 采用非常紧凑的排列，提供稳定的 [2×2] 腙网格阵列。苯环和配合物中垂直配体的腙单元之间的 π-π 堆积诱导了完美的正交排列，适用于自组织金属超分子系统中的应用。锌配合物提供了研究酸碱化学的机会，而不会因顺磁性或氧化还原化学而产生额外影响。中间质子化网格在 NMR 时间尺度上经历相对快速的质子交换，尖锐的嘧啶质子共振的存在表明负电荷沿配体骨架存在显着离域。观察到苯环的旋转。它可能涉及一种机制，其中一个配体部分解离，允许最初插入的苯基在末端吡啶重新配位之前旋转。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim
• DOSY NMR Experiments as a Tool for the Analysis of Constitutional and Motional Dynamic Processes: Implementation for the Driven Evolution of Dynamic Combinatorial Libraries of Helical Strands
  作者：Nicolas Giuseppone、Jean-Louis Schmitt、Lionel Allouche、Jean-Marie Lehn

  DOI：10.1002/anie.200703168

  日期：2008.3.7