5,6-dibenzylthiol-1,10-phenanthroline | 1041480-39-0

• 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-dibenzylthiol-1,10-phenanthroline
• 英文别名: 5,6-bis(benzylthio)-1,10-phenanthroline；5,6-Bis(benzylsulfanyl)-1,10-phenanthroline
• CAS: 1041480-39-0
• 化学式: C₂₆H₂₀N₂S₂
• 分子量: 424.59
• InChiKey: HEJUFSBAPXMTGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,6-dibenzylthiol-1,10-phenanthroline 在 aluminum (III) chloride 、 盐酸 作用下， 以 甲苯 、 水 为溶剂， 生成 1,10-phenanthroline-5,6-dithiol
  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：

  5,6-二溴-1,10-菲罗啉 、 苄硫醇 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以65%的产率得到5,6-dibenzylthiol-1,10-phenanthroline
  参考文献：
  名称：

  TTF-Annulated Phenanthroline and Unexpected Oxidative Cleavage of the C═C Bond in Its Ruthenium(II) Complex

  摘要：

  Tetrathiafulvalene (TTF) and 1,10-phenanthroline have been fused together via a simple and efficient synthetic procedure that provides a new bidentate ligand, 4',5'-ethylenedithiotetrathiafulvenyl[4,5-f]-[1,10]phenanthroline (EDT-TTF-phen, 1). Its ruthenium(II) complex exhibits a unique packing of TTF subunits in the solid state. In an acetonitrile solution, [Ru(bpy)(2)(1)](PF6)(2) undergoes facile oxidative cleavage of the C=C double bond, which cannot be observed in the dark or under anaerobic conditions. This points to the photocatalytic role played by the ruthenium(II) chromophore in this conversion.

  DOI：

  10.1021/ic902230f

文献信息

• Thio-azo proligands based on 5,6-derivatives-1,10-phenanthroline and their use for iron(II) complexes: Synthesis, characterization and crystal structures
  作者：Sandra Rabaça、Maria Carolina Duarte、Isabel C. Santos、Laura C.J. Pereira、Marc Fourmigué、Rui T. Henriques、Manuel Almeida

  DOI：10.1016/j.poly.2008.03.016

  日期：2008.6

  The preparation and characterization of 5,6-substituted-1,10-phenanthrolines, phdtos = 5,6-bistosyl-1,10-phenanthroline (1) and phdbt = 5,6-dibenzyltiol-1,10-phenanthroline (2) are described. The synthesis of (1) was achieved in good yield via the corresponding dihydroxide and 2 was obtained by cross-coupling reaction of 5,6-dibromo-1,10-phenanthroline and benzylthiol mediated by a palladium catalytic system in refluxing toluene (120 degrees C). These phenanthroline derivatives were used as ligands to afford [Fe-II(phdtos)(3)](PF6)(2) (5) and [Fe-II(phdbt)(3)](PF6)(2) (6) complexes. (C) 2008 Elsevier Ltd. All rights reserved.
• 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.
• TTF-Annulated Phenanthroline and Unexpected Oxidative Cleavage of the C═C Bond in Its Ruthenium(II) Complex
  作者：Lawrence K. Keniley、Lipika Ray、Kirill Kovnir、Logan A. Dellinger、Jordan M. Hoyt、Michael Shatruk

  DOI：10.1021/ic902230f

  日期：2010.2.15

  Tetrathiafulvalene (TTF) and 1,10-phenanthroline have been fused together via a simple and efficient synthetic procedure that provides a new bidentate ligand, 4',5'-ethylenedithiotetrathiafulvenyl[4,5-f]-[1,10]phenanthroline (EDT-TTF-phen, 1). Its ruthenium(II) complex exhibits a unique packing of TTF subunits in the solid state. In an acetonitrile solution, [Ru(bpy)(2)(1)](PF6)(2) undergoes facile oxidative cleavage of the C=C double bond, which cannot be observed in the dark or under anaerobic conditions. This points to the photocatalytic role played by the ruthenium(II) chromophore in this conversion.