2,3-dimethyl-pyrido[2,3-f]quinoxaline | 126987-85-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2,3-dimethyl-pyrido[2,3-f]quinoxaline
• 英文别名: 2,3-Dimethylpyrido[2,3-f]quinoxaline
• CAS: 126987-85-7
• 化学式: C₁₃H₁₁N₃
• 分子量: 209.25
• InChiKey: OWIWEYZIKQYCKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  顺-双(2,2'-二吡啶基)二氯化钌(II)二水合物 、 2,3-dimethyl-pyrido[2,3-f]quinoxaline 、 水 以 乙醇 为溶剂， 反应 5.0h， 以92%的产率得到[Ru(2,2′-bipyridine)2(2,3-dimethyl-pyrido[2,3-f]quinoxaline)]Cl2*4H2O
  参考文献：
  名称：

  Controlling Ground and Excited State Properties through Ligand Changes in Ruthenium Polypyridyl Complexes

  摘要：

  The capture and storage of solar energy requires chromophores that absorb light throughout the solar spectrum. We report here the synthesis, characterization, electrochemical, and photophysical properties of a series of Ru(II) polypyridyl complexes of the type [Ru(bpy)(2)(N-N)](2+) (bpy = 2,2'-bipyridine; N-N is a bidentate polypyridyl ligand). In this series, the nature of the N-N ligand was altered, either through increased conjugation or incorporation of noncoordinating heteroatoms, as a way to use ligand electronic properties to tune redox potentials, absorption spectra, emission spectra, and excited state energies and lifetimes. Electrochemical measurements show that lowering the pi* orbitals on the N-N ligand results in more positive Ru3+/2+ redox potentials and more positive first ligand-based reduction potentials. The metal-to-ligand charge transfer absorptions of all of the new complexes are mostly red-shifted compared to Ru(bpy)(3)(2+) (lambda(max) = 449 nm) with the lowest energy MLCT absorption appearing at lambda(max) = 564 nm. Emission energies decrease from lambda(max) = 650 nm to 885 nm across the series. One-mode Franck-Condon analysis of room-temperature emission spectra are used to calculate key excited state properties, including excited state redox potentials. The impacts of ligand changes on visible light absorption, excited state reduction potentials, and Ru3+/2+ potentials are assessed in the context of preparing low energy light absorbers for application in dye-sensitized photoelectrosynthesis cells.

  DOI：

  10.1021/ic500408j
• 作为产物：
  描述：

  7-硝基喹啉 在 盐酸羟胺 、 肼 作用下， 以 乙醇 为溶剂， 生成 2,3-dimethyl-pyrido[2,3-f]quinoxaline
  参考文献：
  名称：

  Controlling Ground and Excited State Properties through Ligand Changes in Ruthenium Polypyridyl Complexes

  摘要：

  The capture and storage of solar energy requires chromophores that absorb light throughout the solar spectrum. We report here the synthesis, characterization, electrochemical, and photophysical properties of a series of Ru(II) polypyridyl complexes of the type [Ru(bpy)(2)(N-N)](2+) (bpy = 2,2'-bipyridine; N-N is a bidentate polypyridyl ligand). In this series, the nature of the N-N ligand was altered, either through increased conjugation or incorporation of noncoordinating heteroatoms, as a way to use ligand electronic properties to tune redox potentials, absorption spectra, emission spectra, and excited state energies and lifetimes. Electrochemical measurements show that lowering the pi* orbitals on the N-N ligand results in more positive Ru3+/2+ redox potentials and more positive first ligand-based reduction potentials. The metal-to-ligand charge transfer absorptions of all of the new complexes are mostly red-shifted compared to Ru(bpy)(3)(2+) (lambda(max) = 449 nm) with the lowest energy MLCT absorption appearing at lambda(max) = 564 nm. Emission energies decrease from lambda(max) = 650 nm to 885 nm across the series. One-mode Franck-Condon analysis of room-temperature emission spectra are used to calculate key excited state properties, including excited state redox potentials. The impacts of ligand changes on visible light absorption, excited state reduction potentials, and Ru3+/2+ potentials are assessed in the context of preparing low energy light absorbers for application in dye-sensitized photoelectrosynthesis cells.

  DOI：

  10.1021/ic500408j

文献信息

• 4-Aza-1, 10-phenanthrolin-Derivate
  申请人：BAYER AG

  公开号：EP0341476A2

  公开（公告）日：1989-11-15

  Neue 4-Aza-1,10-phenanthrolin-Derivate der Formel (I) in welcher R¹ bis R⁶ die in der Beschreibung gegebenen Bedeutungen haben, deren Säureadditionssalze und Metallsalz-Komplexe und ihre Verwendung zur Bekämpfung von Schädlingen. Die neuen 4-Aza-1,10-phenanthrolin-Derivate sind durch die Formel (I) allgemein definiert. Man kann sie nach Analogieverfahren herstellung, z. B. indem man geeignete 5-Aminochinoxaline mit geeigneten Aldehyden umsetzt oder indem man geeignete 7,8-Diaminochinoline mit geeigneten 1,2-Diketonen umsetzt.

  式 (I) 的新型 4-氮杂-1,10-菲罗啉衍生物 其中 R¹至 R⁶具有描述中给出的含义，它们的酸加成盐和金属盐络合物及其在防治害虫中的用途。 新的 4-氮杂-1,10-菲罗啉衍生物一般由式（I）定义。它们可以通过类似的方法制备，例如将合适的 5-氨基喹喔啉与合适的醛反应，或将合适的 7,8-二氨基喹啉与合适的 1,2-二酮反应。
• HEINEMANN, ULRICH;BRANDES, WILHELM;DUTZMANN, STEFAN;HANSS. LER, GERD
  作者：HEINEMANN, ULRICH、BRANDES, WILHELM、DUTZMANN, STEFAN、HANSS. LER, GERD

  DOI：——

  日期：——
• US4965265A
  申请人：——

  公开号：US4965265A

  公开（公告）日：1990-10-23
• Controlling Ground and Excited State Properties through Ligand Changes in Ruthenium Polypyridyl Complexes
  作者：Dennis L. Ashford、Christopher R. K. Glasson、Michael R. Norris、Javier J. Concepcion、Shahar Keinan、M. Kyle Brennaman、Joseph L. Templeton、Thomas J. Meyer

  DOI：10.1021/ic500408j

  日期：2014.6.2

  The capture and storage of solar energy requires chromophores that absorb light throughout the solar spectrum. We report here the synthesis, characterization, electrochemical, and photophysical properties of a series of Ru(II) polypyridyl complexes of the type [Ru(bpy)(2)(N-N)](2+) (bpy = 2,2'-bipyridine; N-N is a bidentate polypyridyl ligand). In this series, the nature of the N-N ligand was altered, either through increased conjugation or incorporation of noncoordinating heteroatoms, as a way to use ligand electronic properties to tune redox potentials, absorption spectra, emission spectra, and excited state energies and lifetimes. Electrochemical measurements show that lowering the pi* orbitals on the N-N ligand results in more positive Ru3+/2+ redox potentials and more positive first ligand-based reduction potentials. The metal-to-ligand charge transfer absorptions of all of the new complexes are mostly red-shifted compared to Ru(bpy)(3)(2+) (lambda(max) = 449 nm) with the lowest energy MLCT absorption appearing at lambda(max) = 564 nm. Emission energies decrease from lambda(max) = 650 nm to 885 nm across the series. One-mode Franck-Condon analysis of room-temperature emission spectra are used to calculate key excited state properties, including excited state redox potentials. The impacts of ligand changes on visible light absorption, excited state reduction potentials, and Ru3+/2+ potentials are assessed in the context of preparing low energy light absorbers for application in dye-sensitized photoelectrosynthesis cells.