1,6-di-(diphenylphosphine)-pyrene | 1093075-84-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,6-di-(diphenylphosphine)-pyrene
• 英文别名: 1,6-bis(diphenylphosphino)pyrene；(6-Diphenylphosphanylpyren-1-yl)-diphenylphosphane
• CAS: 1093075-84-3
• 化学式: C₄₀H₂₈P₂
• 分子量: 570.61
• InChiKey: BDKHOZKUYFPYJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  42
• 可旋转键数：
  6
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,6-di-(diphenylphosphine)-pyrene 在 双氧水 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以85%的产率得到pyrene-1,6-diylbis(diphenylphosphine oxide)
  参考文献：
  名称：

  Metallacyclophanes of 1,6-Bis(diphenylphosphino)pyrene: Excimeric Emission and Effect of Oxygen on Stability of the Rings

  摘要：

  1,6-Bis(diphenylphosphino)pyrene (L) was reacted with Ag(I) and Cu(I) ions to form metallacyclophanes [Ag2L2(OTf)(2)] (1), [Cu2L2(MeCN)(4)](2+) (2), and [Cu2L2I2] (3) which consisted of two cofacial pyrenyl rings. 1 and 2 exhibited intramolecular excimeric emissions which along with the UV-vis absorption were invoked in understanding the solution dynamics of the metallocyclophanes. The metallacyclophanes were stable toward ring-opening dissociation at concentration as low as 10(-7) M. However, air oxidation of the dangling PPh2 groups arising from metal-ligand bond dissociation drove the equilibrium toward dissociation and produced the oxidized phosphine 1,6-bis(diphenylphosphine oxide)pyrene.

  DOI：

  10.1021/ic102441b

文献信息

• Multi‐Stage Redox Systems Based on Dicationic P‐Containing Polycyclic Aromatic Hydrocarbons
  作者：Thomas Delouche、Antoine Vacher、Elsa Caytan、Thierry Roisnel、Boris Le Guennic、Denis Jacquemin、Muriel Hissler、Pierre‐Antoine Bouit

  DOI：10.1002/chem.202001213

  日期：2020.7.2

  based on dicationic P‐containing PAHs (Polycyclic Aromatic Hydrocarbons) based on copper mediated radical approach. In these systems, two phosphoniums are connected through various PAHs backbones. The impact of π‐extension on both the optical and redox properties is investigated using a joint experimental (UV/Vis absorption, fluorescence and cyclic voltammetry) and theoretical approach (TD‐DFT calculations)

  我们报道了基于铜介导的自由基方法，基于含P的指示性PHs（多环芳烃）直接合成了前所未有的电子受体。在这些系统中，两个phospho通过各种PAH骨架连接。使用联合实验（UV / Vis吸收，荧光和循环伏安法）和理论方法（TD-DFT计算）研究了π扩展对光学和氧化还原特性的影响。最后，（光谱）电化学研究证明这些化合物具有三种氧化还原状态，EPR研究证实了在PAH主链上离域的有机自由基的原位形成。
• Switching on the Phosphorescence of Pyrene by Cycloplatination
  作者：Jian Hu、John H. K. Yip、Dik-Lung Ma、Kwok-Yin Wong、Wai-Hong Chung

  DOI：10.1021/om800410m

  日期：2009.1.12

  1-Diphenylphosphinopyrene (1-PyP) and 1,6-bis(diphenylphosphino)pyrene (1,6-PyP) can be metalated at C5 and C10 to give cyclometalated complexes [M(L)(1-PyP-H)](+) and [M-2(L)(2)(1,6-PyP)](2+) (M = Pd or Pt, L = diphosphines). The pi -> pi* transitions of the pyrenyl ring are strongly perturbed by the PPh2, groups at C1/6, while the perturbation of the metal ions at C5/10 is weak. The phosphorescence of the pyrenyl ring is strongly enhanced by the heavy atom effect of the Pt ion up to a quantum yield of 1.5 x 10(-2). Direct coordination of the Pt ion to the pyrenyl ring is needed for enhancement of the phosphorescence.
• Metallacyclophanes of 1,6-Bis(diphenylphosphino)pyrene: Excimeric Emission and Effect of Oxygen on Stability of the Rings
  作者：Jian Hu、Minh-Hai Nguyen、John H. K. Yip

  DOI：10.1021/ic102441b

  日期：2011.8.15

  1,6-Bis(diphenylphosphino)pyrene (L) was reacted with Ag(I) and Cu(I) ions to form metallacyclophanes [Ag2L2(OTf)(2)] (1), [Cu2L2(MeCN)(4)](2+) (2), and [Cu2L2I2] (3) which consisted of two cofacial pyrenyl rings. 1 and 2 exhibited intramolecular excimeric emissions which along with the UV-vis absorption were invoked in understanding the solution dynamics of the metallocyclophanes. The metallacyclophanes were stable toward ring-opening dissociation at concentration as low as 10(-7) M. However, air oxidation of the dangling PPh2 groups arising from metal-ligand bond dissociation drove the equilibrium toward dissociation and produced the oxidized phosphine 1,6-bis(diphenylphosphine oxide)pyrene.