3,6-di(pyrid-2'-yl)-dipyrido[3,2-a:2',3'-c]phenazine | 1008098-09-6

• 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: 3,6-di(pyrid-2'-yl)-dipyrido[3,2-a:2',3'-c]phenazine
• 英文别名: 3,6-Dipyridin-2-ylquinoxalino[2,3-f][1,10]phenanthroline；3,6-dipyridin-2-ylquinoxalino[2,3-f][1,10]phenanthroline
• CAS: 1008098-09-6
• 化学式: C₂₈H₁₆N₆
• 分子量: 436.475
• InChiKey: ZPJDJWNSBILWOY-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 沸点：
  744.2±55.0 °C(Predicted)
• 密度：
  1.382±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,6-di(pyrid-2'-yl)-dipyrido[3,2-a:2',3'-c]phenazine 、 europium(III) trifluoromethanesulfonate 以 甲醇 为溶剂， 以81%的产率得到
  参考文献：
  名称：

  Eu(III) Complexes of Tetradentate Ligands Related to 2,9-Di(pyrid-2′-yl)-1,10-phenanthroline and 2,2′-Bi-1,10-phenanthroline

  摘要：

  A series of six tetradentate polypyridine-type ligands (L) have been used to prepare the corresponding Eu(III) complexes [Eu(L)(2)(S)(n+) (n = 2, 3) where S = H2O or CF3SO3-. Two of the ligands, 2,9-di(pyrid-2'-yl)-1,10-phenanthroline (4) and its dipyridophenazine analogue (6) are symmetrical around a central phenanthroline ring. The other four ligands are 2,2'-bi-1,10-phenanthroline and its 3,3'-di-, tri-, and tetramethylene-bridged analogues (5a-d) whose conformations are governed by the length of the polymethylene bridge. H-1 NMR and X-ray analysis indicate that all of the complexes have a C-2v symmetry. The biphenanthroline series shows a strong correlation of the conjugation between the two halves of the ligand, as governed by the bridge, with the absorption and emission properties of the Eu(III) complex. The complex having the most distorted, tetramethylene-bridged ligand exhibits a weak, high energy pi-pi* absorption and low sensitization efficiency. The luminescence decays are monoexponential for complexes of 4 and either monoexponential or biexponential for the complexes of 5 depending on its solution concentration and the length of the bridge. The complexes of 4 exhibit much longer lifetime, higher overall quantum yield, and higher sensitization efficiency than complexes of 5 while the complex of 6 emits very weakly. The Eu(D-5(0)) lifetime for [Eu(4)(2)(H2O)](ClO4)(3) is shorter than for [Eu(4)(2)(CF3SO3)](CF3SO3)(2), reflecting the effect of the coordinated water. The complexes are examined for stability in the presence of water and found to retain most of their luminescent properties even in the presence of a large excess of water.

  DOI：

  10.1021/ic100338t

文献信息

• Ru(II) Complexes of Tetradentate Ligands Related to 2,9-Di(pyrid-2‘-yl)-1,10-phenanthroline
  作者：Gang Zhang、Ruifa Zong、Huan-Wei Tseng、Randolph P. Thummel

  DOI：10.1021/ic701798v

  日期：2008.2.1

  diimidazoyl system indicates considerable distortion from square planar geometry in the equatorial plane. Previously reported variations in the axial ligand for such complexes appear to have a stronger effect on the electronic absorption and redox properties of the system than similar changes in the equatorial ligand. In the presence of excess Ce(IV) as a sacrificial oxidant at pH 1, all the systems examined

  制备了一系列的1,10-菲咯啉，在2,9-位具有额外的连接取代基。这些取代基是4-取代的吡啶-2-基，喹啉-2-基，1,8-萘啶-2-基，N-甲基咪唑-2-基或N-甲基苯并咪唑-2-基。另外，制备了3,6-二-（吡啶-2'-基）-二吡啶并[3,2-a：2'，3'-c]吩嗪。这些配体中除两个以外的所有配体都以四齿赤道的方式配位Ru（II），在轴向位点结合了两个4-甲基吡啶。对二咪唑基系统的X射线结构分析表明，赤道平面中的方形平面几何结构存在相当大的畸变。先前报道的这类配合物的轴向配体变化似乎比赤道配体的类似变化对系统的电子吸收和氧化还原特性具有更强的影响。在pH为1的过量Ce（IV）作为牺牲氧化剂的情况下，所有检查的系统都催化水分解产生氧气。周转数字适中，范围从146到416。
• Eu(III) Complexes of Tetradentate Ligands Related to 2,9-Di(pyrid-2′-yl)-1,10-phenanthroline and 2,2′-Bi-1,10-phenanthroline
  作者：Ruifa Zong、Gang Zhang、Svetlana V. Eliseeva、Jean-Claude G. Bünzli、Randolph P. Thummel

  DOI：10.1021/ic100338t

  日期：2010.5.17

  A series of six tetradentate polypyridine-type ligands (L) have been used to prepare the corresponding Eu(III) complexes [Eu(L)(2)(S)(n+) (n = 2, 3) where S = H2O or CF3SO3-. Two of the ligands, 2,9-di(pyrid-2'-yl)-1,10-phenanthroline (4) and its dipyridophenazine analogue (6) are symmetrical around a central phenanthroline ring. The other four ligands are 2,2'-bi-1,10-phenanthroline and its 3,3'-di-, tri-, and tetramethylene-bridged analogues (5a-d) whose conformations are governed by the length of the polymethylene bridge. H-1 NMR and X-ray analysis indicate that all of the complexes have a C-2v symmetry. The biphenanthroline series shows a strong correlation of the conjugation between the two halves of the ligand, as governed by the bridge, with the absorption and emission properties of the Eu(III) complex. The complex having the most distorted, tetramethylene-bridged ligand exhibits a weak, high energy pi-pi* absorption and low sensitization efficiency. The luminescence decays are monoexponential for complexes of 4 and either monoexponential or biexponential for the complexes of 5 depending on its solution concentration and the length of the bridge. The complexes of 4 exhibit much longer lifetime, higher overall quantum yield, and higher sensitization efficiency than complexes of 5 while the complex of 6 emits very weakly. The Eu(D-5(0)) lifetime for [Eu(4)(2)(H2O)](ClO4)(3) is shorter than for [Eu(4)(2)(CF3SO3)](CF3SO3)(2), reflecting the effect of the coordinated water. The complexes are examined for stability in the presence of water and found to retain most of their luminescent properties even in the presence of a large excess of water.