3,3'-Dimethylene-2-(2'-pyridyl)benzoquinoline | 154845-28-0

• 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: 3,3'-Dimethylene-2-(2'-pyridyl)benzoquinoline
• 英文别名: 3,3'-dimethylene-2-(2'-pyridyl)benzo[g]quinoline；5,6-Dihydronaphtho[2,3-b][1,10]phenanthroline
• CAS: 154845-28-0
• 化学式: C₂₀H₁₄N₂
• 分子量: 282.345
• InChiKey: NSIQEZCNUZHGOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ammonium hexafluorophosphate 、 顺-双(2,2-二吡啶)二氯化钌(II) 水合物 、 3,3'-Dimethylene-2-(2'-pyridyl)benzoquinoline 以 乙醇 、 水 为溶剂， 以48%的产率得到[Ru(3,3'-dimethylene-2-(2'-pyridyl)benzo[g]quinoline)(2,2'-bipyridine)](PF6)2
  参考文献：
  名称：

  Coexistence of Ligand Localized and MLCT Excited States in a 2-(2‘-Pyridyl)benzo[g]quinoline Complex of Ruthenium(II)

  摘要：

  The photophysical behavior of complexes of the type [(bpy)(2)Ru(L)](PF6)(2), where L is a 2-(2'-pyridyl)quinoline or 2-(2'-pyridyl)benzo[g]quinoline derivative, was investigated in acetonitrile solutions and ethanol-methanol glasses. The luminescence from each complex originates from a metal-to-ligand charge transfer excited state and the energy of the emission maxima correlate with other reported quinoline complexes of Ru(II). The 2-(2'-pyridyl)benzo[g]quinoline complex has a unique transient absorption spectrum with a decay rate constant approximately 30 times less than the luminescence decay rate constant, indicating the existence of two nonequilibrated excited states in the complex. Comparison with other related complexes suggests the long-lived transient absorption may be due to a ligand localized (pi --> pi*) excited state. The pyridylquinoline complex exhibits behavior characteristic of a single MLCT excited state.

  DOI：

  10.1021/ic9412973
• 作为产物：
  描述：

  2-羟基-3-萘甲酸 在 盐酸 、 manganese(IV) oxide 、 氢氧化钾 、 ammonium hydroxide 、 lithium aluminium tetrahydride 、 硫酸 、 三乙胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 为溶剂， 反应 93.0h， 生成 3,3'-Dimethylene-2-(2'-pyridyl)benzoquinoline
  参考文献：
  名称：

  Synthesis and Properties of Ligands Based on Benzo[g]quinoline

  摘要：

  The preparation of 3-amino-2-naphthaldehyde is described. Ammonolysis of 3-hydroxy-8-naphthoic acid affords the corresponding amino acid which can be esterified and then reduced with LAH. Protection of the amino group, MnO2 oxidation of the primary alcohol to an aldehyde, and deprotection gave the amino aldehyde which is an excellent Friedlander synthon for benzo[g]quinolines. Dimethylene-bridged analogues of 2,2'-bipyridine and 2,2';6,2''-terpyridine were prepared as well as orthocyclophanes derived from tetracyclo[6.3.0.0(4,11).0(5,9)]undecane-2,7-dione (TCU-2,7-dione). The absorption and emission spectra of these species are consistent with the parent benzo[g]quinoline where bathochromic shifts result from increased delocalization. The TCU derivative evidences exciplex formation so that its benzo[g]quinoline emission is almost completely quenched and an exciplex emission appears at 525 nm. Electrochemical analysis indicates that both reduction and UV absorption involve the same pi(*) orbital.

  DOI：

  10.1021/jo00083a024