3-benzylidenephthalimidine | 740741-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3-benzylidenephthalimidine
• 英文别名: 3-Benzylideneisoindol-1-amine；3-benzylideneisoindol-1-amine
• CAS: 740741-68-8
• 化学式: C₁₅H₁₂N₂
• 分子量: 220.274
• InChiKey: PHOILJKYFSTXLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-benzylidenephthalimidine 、 zinc diacetate 以 not given 为溶剂， 生成 meso-diphenyltetrabenzoporphyrin zinc
  参考文献：
  名称：

  Optical and redox properties of meso-diphenyltetrabenzoporphyrins

  摘要：

  The meso-diphenyltetrabenzoporphyrin zinc complex (1b, ZnP2TBP) having two phenyl substituents at the neighboring meso-positions was isolated by the careful purification of the reaction product of 3-benzylidenephthalimidine (3-BPI) with zinc acetate. The treatment of 1b with trifluoroacetic acid led to the successful demetalation of 1b to its metal free compound (1e, H2P2TBP). Hence, the other divalent metallic complexes such as magnesium (1a), cadmium (1c) and palladium (1d) were readily prepared by metal insertion into 1e with the appropriate metal sources. The well-defined structural elucidation of these meso-diphenyltetrabenzoporphyrins (P2TBP) has enabled us to determine their electrochemical and optical properties. Among the metallo P2TBPs discussed here, the Mg complex possesses both the lowest oxidation and reduction potentials whilst the Pd complex has the highest oxidation and reduction potentials. This result was explained on the basis of the induction effect on the porphyrin ring current by the central metal ion. The absorption maxima of these metallo P2TBPs were also affected by the central metal ions. Since these TBPs reasonably fluoresce at room temperature and phosphoresce at 77 K as in the case of the corresponding metallotetraphenylporphyrins (TPP), their excited state energies were measurable. Their fluorescence quantum yields (PHI-f)and lifetimes (tau-f) obeyed the heavy atom effect by the central metal ions. Finally, we also discussed their redox properties in the excited states.

  DOI：

  10.1016/s0020-1693(00)81674-6

文献信息

• Optical and redox properties of meso-diphenyltetrabenzoporphyrins
  作者：Madoka Yasuike、Tsuguo Yamaoka、Osamu Ohno、Kunihiro Ichimura、Hisayuki Morii、Masako Sakuragi

  DOI：10.1016/s0020-1693(00)81674-6

  日期：1991.7

  The meso-diphenyltetrabenzoporphyrin zinc complex (1b, ZnP2TBP) having two phenyl substituents at the neighboring meso-positions was isolated by the careful purification of the reaction product of 3-benzylidenephthalimidine (3-BPI) with zinc acetate. The treatment of 1b with trifluoroacetic acid led to the successful demetalation of 1b to its metal free compound (1e, H2P2TBP). Hence, the other divalent metallic complexes such as magnesium (1a), cadmium (1c) and palladium (1d) were readily prepared by metal insertion into 1e with the appropriate metal sources. The well-defined structural elucidation of these meso-diphenyltetrabenzoporphyrins (P2TBP) has enabled us to determine their electrochemical and optical properties. Among the metallo P2TBPs discussed here, the Mg complex possesses both the lowest oxidation and reduction potentials whilst the Pd complex has the highest oxidation and reduction potentials. This result was explained on the basis of the induction effect on the porphyrin ring current by the central metal ion. The absorption maxima of these metallo P2TBPs were also affected by the central metal ions. Since these TBPs reasonably fluoresce at room temperature and phosphoresce at 77 K as in the case of the corresponding metallotetraphenylporphyrins (TPP), their excited state energies were measurable. Their fluorescence quantum yields (PHI-f)and lifetimes (tau-f) obeyed the heavy atom effect by the central metal ions. Finally, we also discussed their redox properties in the excited states.