2,9-bis[p-(2-iodoethoxy)phenyl]-1,10-phenanthroline | 219794-85-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2,9-bis[p-(2-iodoethoxy)phenyl]-1,10-phenanthroline
• 英文别名: 2,9-Bis[4-(2-iodoethoxy)phenyl]-1,10-phenanthroline
• CAS: 219794-85-1
• 化学式: C₂₈H₂₂I₂N₂O₂
• 分子量: 672.304
• InChiKey: ZNDFDZKRNINTIM-UHFFFAOYSA-N

物化性质

• 沸点：
  733.5±60.0 °C(Predicted)
• 密度：
  1.709±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  2,9-bis[p-(2-iodoethoxy)phenyl]-1,10-phenanthroline 、 gold(III) 15,20-bis(3,5-di-tert-butylphenyl)-5,10-bis(4-hydroxyphenyl)porphyrinate hexafluorophosphate 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 以31%的产率得到
  参考文献：
  名称：

  Multiporphyrinic Rotaxanes: Control of Intramolecular Electron Transfer Rate by Steering the Mutual Arrangement of the Chromophores

  摘要：

  A [2]-rotaxane Zn-2-Au+ made from a dumbbell component ended by Zn(II) porphyrin stoppers and a ring component incorporating a Au(III) porphyrin has been assembled in 13% yield using the transition metal templating route. H-1 NMR studies show that its:conformation in solution is very different from those of its complexes with Cu+, Ag+, and Li+. In particular, removal of the templating metal resulted in a changeover of the molecule, the threaded macrocycle undergoing a pirouetting motion placing the Au(III) porphyrin in the deft formed by the two Zn(II) porphyrin stoppers. At room temperature, the changeover could be either complete or partial, depending on the solvent used. Photoinduced electron transfer from one of the Zn(II) porphyrins to the Au(III) porphyrin of the macrocycle was evidenced in the case of the free rotaxane and its Cu(I) complex, Zn2Cu+Au+. In the former case, the photoinduced electron transfer process could be clearly resolved for an extended conformation that is characterized by the Zn(II) porphyrins pointing far from the Au(III) porphyrin electron acceptor, and accounting for 30% of the total in acetonitrile at room temperature. In both Zn2Cu+Au+ and Zn-2-Au+ rotaxanes, the charge-separated state, in which the Zn(II) porphyrin is a cation radical and the Au(III) porphyrin a neutral radical, was generated at a rate of 5 x 10(9) s(-1) and disappeared at a rate of 2 x 10(8) s(-1). In the case of Zn2Cu+Au+, the primary step is very Likely energy transfer from the Zn(II) porphyrin singlet excited state to the MLCT state of the central Cu(I) complex, followed by an electron transfer from the excited Cu(I) unit to the Au(III) porphyrin and a successive charge shift from the Zn(ll) porphyrin to the oxidized Cu(Ll) complex. [2]-rotaxane Zn-2-Au+, in which no bond pathway can be identified between the donor and the, acceptor, is a typical case of electron transfer involving molecular fragments connected by mechanical bonds.

  DOI：

  10.1021/ja002018f
• 作为产物：
  描述：

  2-[4-[9-[4-[2-(4-Methylphenyl)sulfonyloxyethoxy]phenyl]-1,10-phenanthrolin-2-yl]phenoxy]ethyl 4-methylbenzenesulfonate 在 sodium iodide 作用下， 以 丙酮 为溶剂， 生成 2,9-bis[p-(2-iodoethoxy)phenyl]-1,10-phenanthroline
  参考文献：
  名称：

  Complete rearrangement of a multi-porphyrinic rotaxane by metallation–demetallation of the central coordination site

  摘要：

  A new multiporphyrinic [2]rotaxane has been made in which a gold(III) porphyrin is part of the ring; rotation of the stringlike fragment within the ring between two diametrically opposed positions is triggered by metallation-demetallation of the central coordination site.

  DOI：

  10.1039/a805746j

文献信息

• Photoinduced Electron Transfer in Multiporphyrinic Interlocked Structures: The Effect of Copper(I) Coordination in the Central Site
  作者：Lucia Flamigni、Anna Maria Talarico、Jean-Claude Chambron、Valérie Heitz、Myriam Linke、Norifumi Fujita、Jean-Pierre Sauvage

  DOI：10.1002/chem.200305655

  日期：2004.6.7

  Zn-Cu(+)-Au(+), the zinc-porphyrin excited state initially transfers energy to the Cu(I)-phenantholine unit, producing a metal-to-ligand charge-transfer (MLCT) excited state localized on the copper complex with a rate k = 1.4x10(9) s(-1). From this excited state the transfer of an electron to the gold-porphyrin unit takes place, producing the CS state Zn-Cu(2+)-Au(.), which decays with a lifetime of 10 ns. The

  在包含锌（II）卟啉，金（III）卟啉和两个自由菲咯啉结合位点Zn-Au（+）的相应[2]联烷中以及相应的铜（I）菲咯啉络合物中确定了光诱导过程。 ，Zn-Cu（+）-Au（+）。在乙腈溶液中，Zn-Au（+）以两种不同的构型存在：一个扩展的构型L占总数的40％，和一个紧凑的构型S。在L构型中，电子从激发态转移将Zn卟啉与金-卟啉单元（k = 1.3x10（9）s（-1））结合，然后缓慢重组（k = 8.3x10（7）s（-1））还原为基态。S构型的过程无法清楚地解析，但电荷分离（CS）状态迅速形成，并且衰变的寿命约为五十皮秒。在连系的Zn-Cu（+）-Au（+）中，锌卟啉激发态最初将能量转移到Cu（I）-菲咯啉单元，从而产生了以k = 1.4x10（9）s的速率存在于铜配合物中的金属-配体电荷转移（MLCT）激发态。 （-1）。从该激发态开始发生电子向金卟啉单元的转移，产生CS态Zn-Cu（2
• Dramatic effect of the porphyrinic metal on the conformation of a two-ring threaded system
  作者：Myriam Linke、Jean-Claude Chambron、Valérie Heitz、Jean-Pierre Sauvage

  DOI：10.1039/a907284e

  日期：——

  Porphyrin homodimers have been assembled by transition-metal-directed threading of porphyrin-incorporating macrocycles onto a rigid-rod bis-chelate, and the relative orientations of the porphyrins shown to be controlled by the nature of the metal that they contain.

  卟啉同型二聚体是通过过渡金属引导将卟啉大环化合物连接到刚性棒双螯合物上而组装的，并且卟啉的相对方向显示出由它们所含金属的性质控制。
• A [2]-catenane whose rings incorporate two differently metallated porphyrins
  作者：Myriam Linke、Norifumi Fujita、Jean-Claude Chambron、Vale´rie Heitz、Jean-Pierre Sauvage

  DOI：10.1039/b100275a

  日期：——

  A [2]-catenane made with Zn(II) and Au(III) porphyrin-incorporating marcrocycles has been synthesized using the transition metal templated technique, starting from either preformed Au or Zn porphyrin-containing macrocycles. The highest yield (11.5%) was obtained in the latter case. Removal of the copper(I) template metal afforded the free [2]-catenane, whose 1H-NMR properties differ dramatically from those of the parent Cu(I) complex, suggesting a changeover in the molecular structure upon demetallation.

  使用过渡合成了由 Zn(II) 和 Au(III) 卟啉结合大环制成的 [2]-链烯 金属模板技术，从预先形成的含金或锌卟啉大环化合物开始。最高的 在后一种情况下获得了产率（11.5%）。去除铜(I)模板金属得到游离的[2]-链烯， 其 1H-NMR 性质与 母体 Cu(I) 络合物，表明脱金属后分子结构发生了变化。