5,6-bis(2-cyanoethylsulfanyl)-1,10-phenanthroline | 1111633-06-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 5,6-bis(2-cyanoethylsulfanyl)-1,10-phenanthroline
• 英文别名: 3-[[6-(2-Cyanoethylsulfanyl)-1,10-phenanthrolin-5-yl]sulfanyl]propanenitrile；3-[[6-(2-cyanoethylsulfanyl)-1,10-phenanthrolin-5-yl]sulfanyl]propanenitrile
• CAS: 1111633-06-7
• 化学式: C₁₈H₁₄N₄S₂
• 分子量: 350.468
• InChiKey: HPWYRTGYGMWXNG-UHFFFAOYSA-N

物化性质

• 熔点：
  169 °C(Solv: toluene (108-88-3))
• 沸点：
  636.1±55.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二氯二茂钛 、 5,6-bis(2-cyanoethylsulfanyl)-1,10-phenanthroline 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以56%的产率得到cyclopenta-1,3-diene;1,10-phenanthroline-5,6-dithiolate;titanium(4+)
  参考文献：
  名称：

  Dinuclear Ru/Ni, Ir/Ni, and Ir/Pt Complexes with Bridging Phenanthroline-5,6-dithiolate: Synthesis, Structure, and Electrochemical and Photophysical Behavior

  摘要：

  We report the synthesis and full characterization of dinuclear complexes with the bridging ligand phenanthroline-5,6-dithiolate (phendt(2-)) featuring the [Ru(bpy)(2)](2+) or Ir(ppy)(2)](+) fragment at the diimine donor center and the [Ni(dppe)](2+) or [Pt(phen)](2+) complex moiety at the dithiolate group. The molecular structures of the mononuclear complexes [(C5H5)(2)Ti(S,S'-phendt)] and [(ppy)(2)Ir{N,N'-phendt-(C2H4CN)(2)}](PF6) as well as the dinuclear complex [(C5H5)(PPh3)Ru(phendt)Ni(dppe)](PF6) determined by X-ray diffraction (XRD) studies are compared. Photophysical studies with mononuclear [(bpy)(2)Ru{phendt-(C2H4CN)(2)}](2+) and [(ppy)(2)Ir{phendt(C2H4CN)(2)}](+) as well as dinudear [(bpy)(2)Ru(phendt)Ni(dppe)](2+) and [(ppy)(2)Ir(phendt)Ni(dppe)r uncovered an effective luminescence quenching in the dinuclear complexes. Lifetime measurements at room temperature, steady-state measurements at low temperature, electrochemical investigations, and DFT calculations provide evidence for a very efficient energy transfer from the Ru/Ir to the Ni complex moiety with a rate constant k > 5 x 10(9) s(-1). In comparison, the [Ru]phendt[Ni] complex displays a higher quenching efficiency with reduced excited state lifetime, whereas the [Ir]phendt[Ni] complex is characterized by an unaltered lifetime of the thermally equilibrated excited state.

  DOI：

  10.1021/ic4031206
• 作为产物：
  描述：

  2-氰基乙硫醇 、 5,6-二溴-1,10-菲罗啉 在 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以41%的产率得到5,6-bis(2-cyanoethylsulfanyl)-1,10-phenanthroline
  参考文献：
  名称：

  Dinuclear Ru/Ni, Ir/Ni, and Ir/Pt Complexes with Bridging Phenanthroline-5,6-dithiolate: Synthesis, Structure, and Electrochemical and Photophysical Behavior

  摘要：

  We report the synthesis and full characterization of dinuclear complexes with the bridging ligand phenanthroline-5,6-dithiolate (phendt(2-)) featuring the [Ru(bpy)(2)](2+) or Ir(ppy)(2)](+) fragment at the diimine donor center and the [Ni(dppe)](2+) or [Pt(phen)](2+) complex moiety at the dithiolate group. The molecular structures of the mononuclear complexes [(C5H5)(2)Ti(S,S'-phendt)] and [(ppy)(2)Ir{N,N'-phendt-(C2H4CN)(2)}](PF6) as well as the dinuclear complex [(C5H5)(PPh3)Ru(phendt)Ni(dppe)](PF6) determined by X-ray diffraction (XRD) studies are compared. Photophysical studies with mononuclear [(bpy)(2)Ru{phendt-(C2H4CN)(2)}](2+) and [(ppy)(2)Ir{phendt(C2H4CN)(2)}](+) as well as dinudear [(bpy)(2)Ru(phendt)Ni(dppe)](2+) and [(ppy)(2)Ir(phendt)Ni(dppe)r uncovered an effective luminescence quenching in the dinuclear complexes. Lifetime measurements at room temperature, steady-state measurements at low temperature, electrochemical investigations, and DFT calculations provide evidence for a very efficient energy transfer from the Ru/Ir to the Ni complex moiety with a rate constant k > 5 x 10(9) s(-1). In comparison, the [Ru]phendt[Ni] complex displays a higher quenching efficiency with reduced excited state lifetime, whereas the [Ir]phendt[Ni] complex is characterized by an unaltered lifetime of the thermally equilibrated excited state.

  DOI：

  10.1021/ic4031206

文献信息

• Efficient Access to a Versatile 5,6-Dithio-1,10-phenanthroline Building Block and Corresponding Organometallic Complexes
  作者：Bertrand Chesneau、Angélique Passelande、Piétrick Hudhomme

  DOI：10.1021/ol802756w

  日期：2009.2.5

  A facile access to 5,6-bis(2-cyanoethylsulfanyl)-1,10-phenanthroline 1 and its ruthenium(II) bipyridil complex 2, as versatile building blocks for the straightforward synthesis of 5,6-dithio functionalized 1,10-phenanthroline based systems, is described.
• Dinuclear Ru/Ni, Ir/Ni, and Ir/Pt Complexes with Bridging Phenanthroline-5,6-dithiolate: Synthesis, Structure, and Electrochemical and Photophysical Behavior
  作者：David Schallenberg、Antje Neubauer、Elisa Erdmann、Marco Tänzler、Alexander Villinger、Stefan Lochbrunner、Wolfram W. Seidel

  DOI：10.1021/ic4031206

  日期：2014.9.2

  We report the synthesis and full characterization of dinuclear complexes with the bridging ligand phenanthroline-5,6-dithiolate (phendt(2-)) featuring the [Ru(bpy)(2)](2+) or Ir(ppy)(2)](+) fragment at the diimine donor center and the [Ni(dppe)](2+) or [Pt(phen)](2+) complex moiety at the dithiolate group. The molecular structures of the mononuclear complexes [(C5H5)(2)Ti(S,S'-phendt)] and [(ppy)(2)IrN,N'-phendt-(C2H4CN)(2)}](PF6) as well as the dinuclear complex [(C5H5)(PPh3)Ru(phendt)Ni(dppe)](PF6) determined by X-ray diffraction (XRD) studies are compared. Photophysical studies with mononuclear [(bpy)(2)Ruphendt-(C2H4CN)(2)}](2+) and [(ppy)(2)Irphendt(C2H4CN)(2)}](+) as well as dinudear [(bpy)(2)Ru(phendt)Ni(dppe)](2+) and [(ppy)(2)Ir(phendt)Ni(dppe)r uncovered an effective luminescence quenching in the dinuclear complexes. Lifetime measurements at room temperature, steady-state measurements at low temperature, electrochemical investigations, and DFT calculations provide evidence for a very efficient energy transfer from the Ru/Ir to the Ni complex moiety with a rate constant k > 5 x 10(9) s(-1). In comparison, the [Ru]phendt[Ni] complex displays a higher quenching efficiency with reduced excited state lifetime, whereas the [Ir]phendt[Ni] complex is characterized by an unaltered lifetime of the thermally equilibrated excited state.