bis(N-propyl-1,8-naphthalimidyl)amine | 500192-01-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: bis(N-propyl-1,8-naphthalimidyl)amine
• 英文别名: 1,7-Bis(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-4-aza-heptane；2-[3-[3-(1,3-dioxobenzo[de]isoquinolin-2-yl)propylamino]propyl]benzo[de]isoquinoline-1,3-dione
• CAS: 500192-01-8
• 化学式: C₃₀H₂₅N₃O₄
• 分子量: 491.546
• InChiKey: XLNFZBPVGJXYBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  86.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,3'-二氨基二丙基胺 、 1,8-萘二甲酸酐 以 乙醇 为溶剂， 反应 4.0h， 生成 bis(N-propyl-1,8-naphthalimidyl)amine
  参考文献：
  名称：

  Photophysical Study of Bis(naphthalimide)−Amine Conjugates: Toward Molecular Design of Excimer Emission Switching

  摘要：

  The fluorescence properties of two bis(1,8-naphthalimides) with amino-containing spacers are investigated, giving special emphasis to the observation of excimer emission. It is found that a minor elongation of the spacer by two methylene units gives rise to a quantitative shut down of the broad and red-shifted excimer emission. Furthermore, a switching of this emission is established through manipulation of a photoinduced electron transfer process, which involves the amino spacer. Protons as well as protic solvents lead to substantial excimer emission with lifetimes of 12 to 27 ns. The excimer quantum yield takes a maximum value of Phi(f) = 0.07 (acetonitrile with 1 equiv trifluoroacetic acid). The increased virtual Stokes shifts (ca. 150 nm) as compared to the fluorescence of monomeric 1,8-naphthalimides are an alternative approach to obtain colored, significant, and long-lived fluorescence from these chromophores. As an additional excited state pathway, the occurrence of homo-Forster resonance energy transfer (homo-FRET) is established by fluorescence polarization measurements and calculation of the corresponding critical Forster radius (R-0 ca. 13 angstrom). The average interchromophore distance between the naphthalimides is estimated as 7.5 angstrom and 9.5 angstrom for the dyad with the shorter and the longer spacer, respectively. These observations and the absence of a rise time component for excimer emission are in agreement with the formation of a "loose" ground state dimer, which upon excitation undergoes a fast geometrical adjustment to the excimer structure where the chromophores are at contact distance.

  DOI：

  10.1021/jp110470h