N,N'-dioctyl-1-pyrrolidinyl-6-(dipyridophenazinoxy)perylene-3,4,9,10-tetracarboxy diimide | 1450646-70-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N,N'-dioctyl-1-pyrrolidinyl-6-(dipyridophenazinoxy)perylene-3,4,9,10-tetracarboxy diimide
• 英文别名: 7,18-Dioctyl-11-pyrrolidin-1-yl-26-quinoxalino[3,2-f][1,10]phenanthrolin-10-yloxy-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2(26),3,5(25),9,11,13(23),14,16(24),20-decaene-6,8,17,19-tetrone
• CAS: 1450646-70-4
• 化学式: C₆₂H₅₇N₇O₅
• 分子量: 980.178
• InChiKey: GQDIOWOFKKGIAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.9
• 重原子数：
  74
• 可旋转键数：
  17
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  139
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  顺-双(2,2-二吡啶)二氯化钌(II) 水合物 、 ammonium hexafluorophosphate 、 N,N'-dioctyl-1-pyrrolidinyl-6-(dipyridophenazinoxy)perylene-3,4,9,10-tetracarboxy diimide 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以49%的产率得到[Ru(bpy)₂(N,N'-dioctyl-1-pyrrolidinyl-6-(dipyridophenazinoxy)perylene-3,4,9,10-tetracarboxy diimide)](PF6)₂
  参考文献：
  名称：

  Excited-State Interaction of Red and Green Perylene Diimides with Luminescent Ru(II) Polypyridine Complex

  摘要：

  Three new perylene diimide (PDI)-based ligands have been synthesized by the covalent attachment of dipyrido[a,c]phenazine moiety to one of the bay positions of PDI, while the second position has been substituted with either a 4-tert-butylphenoxy or a 7 ET pyrrolidinyl group to obtain two types of chromophores, Ph-PDI and Py-PDI, respectively, with distinct properties. In the case of Py-PDI, the resultant 1,7- and 1,6-regioisoMers have been successfully separated. by column chromatography and characterized by H-1 NMR spectroscopy. The ligands have been employed to prepare donor acceptor-based ensembles incorporating the covalently linked PDI and Ru(II) polypyridine complex as the acting chromophores. A comprehensive study of excited state photodynamics.of the ensembles has been performed by means, of electrochemical and steady state and time, resolved spectroscopic methods. Although, in all the three ensembles, the photoexcitation of either chromophore resulted in a long-lived triplet excited state of PDI ((PDI)-P-3) as the final excited state, the photochemical reactions leading to the triplet states were found to be essentially different for the two types of the ensembles. In the case of the Ph-PDI-based ensemble, the excitation of either chromophore leads to the electron transfer from the Ru(II) complex to Ph-PDI, whereas for the Py-PDI-based ensembles, the electron transfer is observed in the opposite direction and only when the Ru(II) complex is excited. The difference in the behavior was rationalized based on electrochemical study of the compounds, which has shown that the Ph-PDI chromophore is a better electron acceptor and the Py-PDI chromophores are relatively better electron donors. This study shows a chemical approach to control the photoreactions in PDI-based dichromophoric ensembles including the possibility to switch the direction of the photoinduced electron transfer.

  DOI：

  10.1021/ic400474b