4,5-bis(trimethylsilyl)pyridazine

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 4,5-bis(trimethylsilyl)pyridazine
• 英文别名: 4,5-(Me3Si)2pyridazine；Trimethyl-(5-trimethylsilylpyridazin-4-yl)silane
• 化学式: C₁₀H₂₀N₂Si₂
• 分子量: 224.453
• InChiKey: XQFOVXJHQXPDRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.57
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  五羰基氯铼(I) 、 4,5-bis(trimethylsilyl)pyridazine 以 not given 为溶剂， 生成 Re2(μ-Cl)2(CO)6(μ-4,5-(Me3Si)2pyridazine)
  参考文献：
  名称：

  Highly Emitting Concomitant Polymorphic Crystals of a Dinuclear Rhenium Complex

  摘要：

  The dinuclear complex [Re-2(mu-Cl)(2)(CO)(6)(mu-4,5-(Me3Si)(2)-pyridazine)] gives in the solid state two polymorphs (yellow, 1Y, and orange, 10), which can be either concomitantly or separately obtained on varying the crystallization rate. Both crystal phases exhibit intense photoluminescence from the lowest lying triplet metal-to-ligand charge transfer state, much stronger than in solution (quantum yields 0.56 and 0.52, for 10 and 1Y respectively, vs 0.06 in toluene), likely due to the restricted rotation of the Me3Si groups in the solid state. A clean, irreversible 10 -> 1Y single-crystal-to-single-crystal phase transition occurs at 443 K, as revealed by variable temperature X-ray diffraction analysis. In spite of the absence of any strong intermolecular interactions in both forms, 10 and 1Y show very different absorption and emission maxima (lambda(abs) 370 and 393 nm, lambda(em) 534 and 570 nm, for 1Y and 10, respectively). This behavior highlights the importance of the local organization of molecular dipoles in perturbing the photophysical properties of the molecule in the crystal.

  DOI：

  10.1021/ja106772v
• 作为产物：
  描述：

  1,2,4,5-四嗪 、 二(三甲基甲硅烷基)乙炔 以 1,4-二氧六环 为溶剂， 反应 12.0h， 生成 4,5-bis(trimethylsilyl)pyridazine
  参考文献：
  名称：

  Highly Emitting Concomitant Polymorphic Crystals of a Dinuclear Rhenium Complex

  摘要：

  The dinuclear complex [Re-2(mu-Cl)(2)(CO)(6)(mu-4,5-(Me3Si)(2)-pyridazine)] gives in the solid state two polymorphs (yellow, 1Y, and orange, 10), which can be either concomitantly or separately obtained on varying the crystallization rate. Both crystal phases exhibit intense photoluminescence from the lowest lying triplet metal-to-ligand charge transfer state, much stronger than in solution (quantum yields 0.56 and 0.52, for 10 and 1Y respectively, vs 0.06 in toluene), likely due to the restricted rotation of the Me3Si groups in the solid state. A clean, irreversible 10 -> 1Y single-crystal-to-single-crystal phase transition occurs at 443 K, as revealed by variable temperature X-ray diffraction analysis. In spite of the absence of any strong intermolecular interactions in both forms, 10 and 1Y show very different absorption and emission maxima (lambda(abs) 370 and 393 nm, lambda(em) 534 and 570 nm, for 1Y and 10, respectively). This behavior highlights the importance of the local organization of molecular dipoles in perturbing the photophysical properties of the molecule in the crystal.

  DOI：

  10.1021/ja106772v

文献信息

• Steric and electronic effects on the ¹ H hyperpolarisation of substituted pyridazines by signal amplification by reversible exchange
  作者：Peter J. Rayner、Michael J. Burns、Elizabeth J. Fear、Simon B. Duckett

  DOI：10.1002/mrc.5152

  日期：2021.12

  rapid and cost-effective hyperpolarisation of substituted pyridazines. The 33 substrates investigated cover a range of steric and electronic properties and their capacity to perform highly effective SABRE is assessed. We find the method to be tolerant to a broad range of electron donating and withdrawing groups; however, good sensitivity is evident when steric bulk is added to the 3- and 6-positions of

  哒嗪基序作为药物和农用化学品的用途越来越受欢迎。因此，此类材料的检测和结构表征对于新产品的成功开发至关重要。可逆交换信号放大（SABRE）提供了一种显着提高磁共振方法灵敏度的途径，我们将其应用于取代哒嗪的快速且经济有效的超极化。研究的 33 种基材涵盖了一系列空间和电子特性，并评估了它们执行高效 SABRE 的能力。我们发现该方法能够耐受广泛的给电子基团和吸电子基团；然而，当空间体积添加到哒嗪环的 3 位和 6 位时，明显具有良好的灵敏度。我们通过参考二取代酯来优化该方法，该二取代酯在 9.4 T 下产生 > 9000 倍的信号增益（> 28% 自旋极化）。
• Synthesis of metallated (metal = Si, Ge, Sn) pyridazines by cycloaddition of metal substituted alkynes to 1,2,4,5-tetrazine
  作者：Dieter K Heldmann、Jürgen Sauer

  DOI：10.1016/s0040-4039(97)01279-3

  日期：1997.8

  MR3-substituted alkynes 2 and 3 (M = Si, Ge, Sn; R = alkyl) show high reactivity in inverse-type Diels-Alder reactions with the R-electron-deficient 1,2,4,5-tetrazine 1 in strict contrast to the corresponding carbon compounds. Kinetic data prove the huge accelerating effect of the trialkyltin substituent, offering a simple access to new heteroaromatic organotin derivatives, which can be easily transformed by standard methods of organotin chemistry. (C) 1997 Elsevier Science Ltd.
• Highly Emitting Concomitant Polymorphic Crystals of a Dinuclear Rhenium Complex
  作者：Elsa Quartapelle Procopio、Matteo Mauro、Monica Panigati、Daniela Donghi、Pierluigi Mercandelli、Angelo Sironi、Giuseppe D’Alfonso、Luisa De Cola

  DOI：10.1021/ja106772v

  日期：2010.10.20

  The dinuclear complex [Re-2(mu-Cl)(2)(CO)(6)(mu-4,5-(Me3Si)(2)-pyridazine)] gives in the solid state two polymorphs (yellow, 1Y, and orange, 10), which can be either concomitantly or separately obtained on varying the crystallization rate. Both crystal phases exhibit intense photoluminescence from the lowest lying triplet metal-to-ligand charge transfer state, much stronger than in solution (quantum yields 0.56 and 0.52, for 10 and 1Y respectively, vs 0.06 in toluene), likely due to the restricted rotation of the Me3Si groups in the solid state. A clean, irreversible 10 -> 1Y single-crystal-to-single-crystal phase transition occurs at 443 K, as revealed by variable temperature X-ray diffraction analysis. In spite of the absence of any strong intermolecular interactions in both forms, 10 and 1Y show very different absorption and emission maxima (lambda(abs) 370 and 393 nm, lambda(em) 534 and 570 nm, for 1Y and 10, respectively). This behavior highlights the importance of the local organization of molecular dipoles in perturbing the photophysical properties of the molecule in the crystal.