5,6-bis(pyren-1-ylethynyl)-1,10-phenanthroline | 1141507-82-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 5,6-bis(pyren-1-ylethynyl)-1,10-phenanthroline
• 英文别名: 5,6-Bis(2-pyren-1-ylethynyl)-1,10-phenanthroline
• CAS: 1141507-82-5
• 化学式: C₄₈H₂₄N₂
• 分子量: 628.732
• InChiKey: WUCRIOJKECXFML-UHFFFAOYSA-N

物化性质

• 密度：
  1.43±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.7
• 重原子数：
  50
• 可旋转键数：
  4
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5,6-二溴-1,10-菲罗啉 、 1-乙炔基芘 在 四(三苯基膦)钯 、 二异丙胺 作用下， 以 苯 为溶剂， 以75%的产率得到5,6-bis(pyren-1-ylethynyl)-1,10-phenanthroline
  参考文献：
  名称：

  Synthesis, Electrochemical and Optical Properties of Ru ^II –Diphenylphenanthroline–Ethynylpyrenephenanthroline Systems

  摘要：

  AbstractThe synthesis, electrochemical and optical spectroscopic properties of a RuII–diphenylphenanthroline complex decorated with ethynylpyrene (EP) appendages, 1, and those of its parent bromo‐substituted complex, 2, are reported; complex 1 is [Ru(dpp)2(phen–EP2)](PF6)2 and 2 is [Ru(dpp)2(phen–Br2)](PF6)2, where dpp is 4,7‐diphenyl‐1,10‐phenanthroline, phen–EP is 5,6‐(1‐ethynylpyrene)‐1,10‐phenanthroline and phen–Br2 is 5,6‐dibromo‐1,10‐phenanthroline. In CH3CN solvent, both bromo‐ and EP‐substituted complexes are redox active and metal‐centred and ligand‐centred processes are assigned with reference to the analogous steps for [Ru(phen)3]2+ and to steps for the EP appendages. The complexes exhibit strong absorption bands in the near‐UV and visible regions due to ligand‐centred (LC) and metal‐to‐ligand charge‐transfer (MLCT) transition, respectively. For 1, the lowest‐lying absorption band is slightly redshifted due to better delocalisation at the phen–EP ligand. At room temperature and in O2‐free solvent, complex 1 appeared to be practically nonluminescent, whereas 2 exhibited intense 3MLCT emission; quantum yields of fem = 9 × 10–4 and 6.1 × 10–2 were found for 1 and 2, respectively and λexc = 462 nm in both cases. The lowest‐lying excited states of 1 were assigned as 3LC states, which were localised on the EP moiety. These states are nonluminescent, which thus explains the weak room‐temperature luminescence for this complex. At 77 K, 2 is emissive, as expected for 3MLCT levels; however, a moderately intense 3MLCT emission was also observed for 1 at this temperature. For the latter case, this outcome is tentatively explained in terms of local trapping of 3MLCT states at the 4,7‐diphenylphenanthroline ligands free of EP appendages.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  DOI：

  10.1002/ejic.200701097