1,10-亚铁试剂(邻二氮杂菲),3,8-二[(4-甲氧苯基)乙炔基]- | 168003-71-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 中文名称: 1,10-亚铁试剂(邻二氮杂菲),3,8-二[(4-甲氧苯基)乙炔基]-
• 英文名称: 3,8-di(4-methoxyphenylethynyl)-1,10-phenanthroline
• 英文别名: 3,8-Bis[(4-methoxyphenyl)ethynyl]-1,10-phenanthroline；3,8-bis[2-(4-methoxyphenyl)ethynyl]-1,10-phenanthroline
• CAS: 168003-71-2
• 化学式: C₃₀H₂₀N₂O₂
• 分子量: 440.501
• InChiKey: RKCGKSMXDAEOKI-UHFFFAOYSA-N

物化性质

• 沸点：
  679.4±55.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  锇二(2,2'-联吡啶)氯化物 、 氟硼酸铵 、 1,10-亚铁试剂(邻二氮杂菲),3,8-二[(4-甲氧苯基)乙炔基]- 以 乙二醇 为溶剂， 以79%的产率得到osmium(II) bis(2,2'-bipyridine) (3,8-di(4-methoxyphenylethynyl)-1,10-phenanthroline) bistetrafluoroborate
  参考文献：
  名称：

  Synthesis and near IR photoluminescence of Os(II) bis(2,2′-bipyridine) (3,8-diarylethynyl-1,10-phenanthroline) complexes: anomalous behavior in the 3,8-dinitrophenylethynyl-substituted homologue

  摘要：

  A large bathochromic shift (greater than or equal to50 nm) and emission in the near infrared is observed by attaching arylethynyl groups at the 3,8-positions of the 1,10-phenanthroline ligand (phen) of [Os(bipy)(2)(phen)](2+) (where bipy = 2,2'-bipyridine). Thus [Os(bipy)(2)(3,8-di-4-methoxyphenylethynyl-1,10-phenathroline)](2+) emits at 795 nm, while [Os(bipy)(2)(3,8-diphenylethynyl-1,10-phenanthroline)](2+) emits at 815 nm. According to this trend it would have been expected that [Os(bipy)2(3,8-di-4-nitrophenylethynyl-1,10-phenathroline)](2+) emits farther in the near infrared. Nevertheless, this complex is not photoluminescent because of intramolecular electron transfer quenching of the MLCT excited state by the nitroaromatic group. These results set structural and redox potential standards in the design of near infrared emitters based on [Os(bipy)(2)(phen)](2+) type complexes. Published by Elsevier B.V.

  DOI：

  10.1016/j.ica.2004.08.012
• 作为产物：
  描述：

  3,8-二溴菲罗啉 、 4-乙炔基苯甲醚 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以89%的产率得到1,10-亚铁试剂(邻二氮杂菲),3,8-二[(4-甲氧苯基)乙炔基]-
  参考文献：
  名称：

  Tuning the electronic properties of phenanthroline ligands: 3,8-bis(arylethynyl)-1,10-phenanthrolines and their Ru(II) complexes

  摘要：

  Palladium-catalyzed cross-coupling reactions between 3,8-dibromo-1,10-phenanthroline and substituted phenylacetylenes provide a navel family of highly conjugated metal chelators. The electronic transitions of the ligands and their Ru(II) complexes are affected by the nature of the substituents on the conjugated phenyl rings.

  DOI：

  10.1016/0040-4039(95)01190-s

文献信息

• Synthesis and near IR photoluminescence of Os(II) bis(2,2′-bipyridine) (3,8-diarylethynyl-1,10-phenanthroline) complexes: anomalous behavior in the 3,8-dinitrophenylethynyl-substituted homologue
  作者：Jinhua Yang、Amala Dass、Chariklia Sotiriou-Leventis、Daniel S. Tyson、Nicholas Leventis

  DOI：10.1016/j.ica.2004.08.012

  日期：2005.1

  A large bathochromic shift (greater than or equal to50 nm) and emission in the near infrared is observed by attaching arylethynyl groups at the 3,8-positions of the 1,10-phenanthroline ligand (phen) of [Os(bipy)(2)(phen)](2+) (where bipy = 2,2'-bipyridine). Thus [Os(bipy)(2)(3,8-di-4-methoxyphenylethynyl-1,10-phenathroline)](2+) emits at 795 nm, while [Os(bipy)(2)(3,8-diphenylethynyl-1,10-phenanthroline)](2+) emits at 815 nm. According to this trend it would have been expected that [Os(bipy)2(3,8-di-4-nitrophenylethynyl-1,10-phenathroline)](2+) emits farther in the near infrared. Nevertheless, this complex is not photoluminescent because of intramolecular electron transfer quenching of the MLCT excited state by the nitroaromatic group. These results set structural and redox potential standards in the design of near infrared emitters based on [Os(bipy)(2)(phen)](2+) type complexes. Published by Elsevier B.V.
• Tuning the electronic properties of phenanthroline ligands: 3,8-bis(arylethynyl)-1,10-phenanthrolines and their Ru(II) complexes
  作者：Dimitrios Tzalis、Yitzhak Tor

  DOI：10.1016/0040-4039(95)01190-s

  日期：1995.8

  Palladium-catalyzed cross-coupling reactions between 3,8-dibromo-1,10-phenanthroline and substituted phenylacetylenes provide a navel family of highly conjugated metal chelators. The electronic transitions of the ligands and their Ru(II) complexes are affected by the nature of the substituents on the conjugated phenyl rings.