N-hydroxy-N-(3-pyren-1-ylpropyl)acetamide | 163455-80-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: N-hydroxy-N-(3-pyren-1-ylpropyl)acetamide
• CAS: 163455-80-9
• 化学式: C₂₁H₁₉NO₂
• 分子量: 317.387
• InChiKey: DRQSFIZFGJLKJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ferric nitrate 、 N-hydroxy-N-(3-pyren-1-ylpropyl)acetamide 以 四氢呋喃 、 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Metal-Induced Self-Assembly of a Pyrene-Tethered Hydroxamate Ligand for the Generation of Multichromophoric Supramolecular Systems. The Pyrene Excimer as Switch for Iron(III)-Driven Intramolecular Fluorescence Quenching

  摘要：

  We report the first example of intramolecular excimer formation in supramolecular trichromophoric systems resulting from the metal-directed self-assembly of chromophore-labeled ligand molecules. The trichromophoric gallium(III) chelate, (1)(3)Ga, shows an intense pyrene excimer fluorescence emission in acetonitrile, while the iron(III) analogue, (1)(3)Fe, exhibits a fluorescence of very low intensity compared to that of the free hydroxamate ligand 1. The trivalent gallium metal cation is demonstrated to play the role of an inert and transparent linker, whereas the ferric center acts additionally as an extra chromophore that quenches the pyrene singlet state. On the basis of low-temperature fluorescence measurements, the mechanism of quenching within (l)(3)Fe is attributed to a pyrene-to-iron electronic energy transfer process. (1)H NMR and electronic absorption spectroscopies show that intramolecular interactions between pyrene chromophores prevail in the ground state, which leads to the formation of preassociated excimers for both chelates. From the dependence of the solvent on the photophysical properties of (1)3Ga and (1)3Fe, it is inferred that the Fe(III)-induced quenching process is triggered by the ground-state and excited-state intramolecular dimerization of the pyrene moieties, with the pyrene-to-iron energy transfer taking place more readily from the excimer singlet state as donor than from the locally excited state.

  DOI：

  10.1021/ja980368k
• 作为产物：
  描述：

  N-Benzyloxy-N-(3-pyren-1-yl-propyl)-acetamide 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以28%的产率得到N-hydroxy-N-(3-pyren-1-ylpropyl)acetamide
  参考文献：
  名称：

  -系异羟肟酸配体的合成，金属键合和荧光研究

  摘要：

  描述了a共轭异羟肟酸衍生物及其Fe（III）和Ga（III）配合物的合成和表征。该络合物是三色性组装体，其表现出强烈依赖于金属原子的性质的荧光发射特征。

  DOI：

  10.1016/0040-4039(95)00028-b