3,8-bis-(2-pyridyl)-4,7-phenanthroline | 322400-45-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3,8-bis-(2-pyridyl)-4,7-phenanthroline
• 英文别名: 3,8-Bis(2-pyridyl)-4,7-phenanthroline；3,8-Dipyridin-2-yl-4,7-phenanthroline；3,8-dipyridin-2-yl-4,7-phenanthroline
• CAS: 322400-45-3
• 化学式: C₂₂H₁₄N₄
• 分子量: 334.38
• InChiKey: QTCFCKJFQWWEJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  六氟磷酸钾 、 [iridium(III)(μ-chloro)(2-phenylpyridine)2]2 、 水 、 3,8-bis-(2-pyridyl)-4,7-phenanthroline 以 甲醇 、 水 为溶剂， 以94%的产率得到[Ir2(2-phenylpyridine-C2,N')4(3,8-bis-(2-pyridyl)-4,7-phenanthroline)](PF6)2*water
  参考文献：
  名称：

  由Ir（ppy）（2）单元（ppy = 2-苯基吡啶）和两个侧向连接的N / N螯合物组成的双金属铱（III）配合物：合成，分离和光物理性质。

  摘要：

  前体络合物Ir2（ppy）4Cl2（ppy = 2-苯基吡啶）与桥联配体3,8-二吡啶基-4,7-菲咯啉（L）的反应以94％的收率提供了环金属化铱双核络合物[（ppy ）2Ir（mu-L）Ir（ppy）2] 2+（12+）作为三种立体异构体的混合物。该混合物由内消旋形式的Delta，Lambda和外消旋形式（对映体对Delta，Delta和Lambda，Lambda）以1：1.5的比例组成。内消旋体形式的高氯酸盐的单晶X射线表征揭示了（i）桥接配体因平面度而发生的变形以及（ii）两个铱亚基在桥接配体中平面上方和下方的位置。用Delta-TRISPHAT阴离子（TRISPHAT =三（四氯苯并二羟基氨基甲酸）磷酸（V））作为离子对的离子对色谱可分离三种立体异构体。每个部分的1 H NMR光谱分析表明非对映异构体纯度高。电子圆二色性和与文献数据的比较建立了它们的绝对构型。三种立体异构体的吸收和

  DOI：

  10.1021/ic700494e
• 作为产物：
  描述：

  4,7-Dimethyl-4,7-phenanthrolinium diiodide 在 四(三苯基膦)钯 sodium hydroxide 、 三溴化磷 、 potassium hexacyanoferrate(III) 、 三溴氧磷 作用下， 以 甲苯 为溶剂， 反应 85.5h， 生成 3,8-bis-(2-pyridyl)-4,7-phenanthroline
  参考文献：
  名称：

  Adaptive Self-Assembly: Environment-Induced Formation and Reversible Switching of Polynuclear Metallocyclophanes

  摘要：

  Ligand 3 has been shown to self-assemble under coordination of copper(II) cations in a 1:1 ratio in acetonitrile to give equilibrating mixtures of a [2 x 2] grid-type tetranuclear structure 1 and a hexanuclear achitecture of hexagonal shape 2. The latter was confirmed by determination of the crystal structure which further indicated that 2 contained acetonitrile molecules and hydroxo groups bound to the copper(II) centers, which are therefore five-coordinate. The structures assigned to 1 and 2 were further supported by the spectral (mass, UV/Vis) data. The self-assembly process is strongly dependent on the conditions of the medium. An increase in concentration in acetronitrile increases the relative amount of hexamer 2, which appears to be the favored entity at the highest concentrations that can be reached before precipitation occurs. On the other hand, in nitromethane only the tetranuclear complex 1 was detected by mass spectrometry. Replacement of nitromethane by acetonitrile and vice versa indicated the reversible switching between a solution containing either 1 alone or an equilibrium mixture of 1 and 2, respectively. In conclusion, the system described presents several remarkable features: 1) self-assembly with substrate binding, 2) dynamic combinatorial structure generation, and 3) environment-induced structural switching amounting in effect to a process of adaptive self-assembly.

  DOI：

  10.1002/1521-3765(20001117)6:22<4140::aid-chem4140>3.0.co;2-5

文献信息

• Adaptive Self-Assembly: Environment-Induced Formation and Reversible Switching of Polynuclear Metallocyclophanes
  作者：Paul N. W. Baxter、Richard G. Khoury、Jean-Marie Lehn、Gerhard Baum、Dieter Fenske

  DOI：10.1002/1521-3765(20001117)6:22<4140::aid-chem4140>3.0.co;2-5

  日期：2000.11.17

  Ligand 3 has been shown to self-assemble under coordination of copper(II) cations in a 1:1 ratio in acetonitrile to give equilibrating mixtures of a [2 x 2] grid-type tetranuclear structure 1 and a hexanuclear achitecture of hexagonal shape 2. The latter was confirmed by determination of the crystal structure which further indicated that 2 contained acetonitrile molecules and hydroxo groups bound to the copper(II) centers, which are therefore five-coordinate. The structures assigned to 1 and 2 were further supported by the spectral (mass, UV/Vis) data. The self-assembly process is strongly dependent on the conditions of the medium. An increase in concentration in acetronitrile increases the relative amount of hexamer 2, which appears to be the favored entity at the highest concentrations that can be reached before precipitation occurs. On the other hand, in nitromethane only the tetranuclear complex 1 was detected by mass spectrometry. Replacement of nitromethane by acetonitrile and vice versa indicated the reversible switching between a solution containing either 1 alone or an equilibrium mixture of 1 and 2, respectively. In conclusion, the system described presents several remarkable features: 1) self-assembly with substrate binding, 2) dynamic combinatorial structure generation, and 3) environment-induced structural switching amounting in effect to a process of adaptive self-assembly.
• Bimetallic Iridium(III) Complexes Consisting of Ir(ppy)₂ Units (ppy = 2-Phenylpyridine) and Two Laterally Connected N^∧N Chelates as Bridge:  Synthesis, Separation, and Photophysical Properties
  作者：Audrey Auffrant、Andrea Barbieri、Francesco Barigelletti、Jérôme Lacour、Pierre Mobian、Jean-Paul Collin、Jean-Pierre Sauvage、Barbara Ventura

  DOI：10.1021/ic700494e

  日期：2007.8.1

  analysis of each fraction indicates high diastereomeric purity. Electronic circular dichroism properties and comparison with literature data establish their absolute configuration. The absorption and emission properties of the three stereoisomers show only very small variations. The anisotropic properties can be interpreted as distinct interactions of the isomers with the chiral resolving Delta-TRISPHAT

  前体络合物Ir2（ppy）4Cl2（ppy = 2-苯基吡啶）与桥联配体3,8-二吡啶基-4,7-菲咯啉（L）的反应以94％的收率提供了环金属化铱双核络合物[（ppy ）2Ir（mu-L）Ir（ppy）2] 2+（12+）作为三种立体异构体的混合物。该混合物由内消旋形式的Delta，Lambda和外消旋形式（对映体对Delta，Delta和Lambda，Lambda）以1：1.5的比例组成。内消旋体形式的高氯酸盐的单晶X射线表征揭示了（i）桥接配体因平面度而发生的变形以及（ii）两个铱亚基在桥接配体中平面上方和下方的位置。用Delta-TRISPHAT阴离子（TRISPHAT =三（四氯苯并二羟基氨基甲酸）磷酸（V））作为离子对的离子对色谱可分离三种立体异构体。每个部分的1 H NMR光谱分析表明非对映异构体纯度高。电子圆二色性和与文献数据的比较建立了它们的绝对构型。三种立体异构体的吸收和