6-Octyl-2-[4-[tris[4-(2-pyridin-4-ylethynyl)phenyl]methyl]phenyl]pyrrolo[3,4-f]isoindole-1,3,5,7-tetrone | 1335154-42-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 6-Octyl-2-[4-[tris[4-(2-pyridin-4-ylethynyl)phenyl]methyl]phenyl]pyrrolo[3,4-f]isoindole-1,3,5,7-tetrone
• 英文别名: 6-octyl-2-[4-[tris[4-(2-pyridin-4-ylethynyl)phenyl]methyl]phenyl]pyrrolo[3,4-f]isoindole-1,3,5,7-tetrone
• CAS: 1335154-42-1
• 化学式: C₆₄H₄₇N₅O₄
• 分子量: 950.108
• InChiKey: ADJITELCVKXXSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.7
• 重原子数：
  73
• 可旋转键数：
  18
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-乙炔基吡啶 、 N-[4-{tris(4-bromophenyl)methyl}phenyl]-N'-(n-octyl)pyromellitdiimide 在 copper(l) iodide 、 二(氰基苯)二氯化钯 、 二异丙胺 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 1,4-二氧六环 为溶剂， 反应 11.0h， 以44%的产率得到6-Octyl-2-[4-[tris[4-(2-pyridin-4-ylethynyl)phenyl]methyl]phenyl]pyrrolo[3,4-f]isoindole-1,3,5,7-tetrone
  参考文献：
  名称：

  Fullerene- and Pyromellitdiimide-Appended Tripodal Ligands Embedded in Light-Harvesting Porphyrin Macrorings

  摘要：

  Three new tripyridyl tripodal ligands appended with either fullerene or pyromellitdiimide moieties, named C(60)-s-Tripod, C(60)-l-Tripod, and PI Tripod, were synthesized and introduced into a porphyrin macroring N-(1-Zn)(3) (where 1-Zn = trisporphyrinatozinc(II)). From UV-vis absorption and fluorescence titration data, the bindin constants of C(60)-s-Tripod, C(60)-l-Tripod, and PI-Tripod with N-(1-Zn)(3) in benzonitrile were estimated to be 3 X 10(8), 1 X 10(7), and 2 x 10(7) M(-1), respectively. These large binding constants denote multiple interactions of the ligands to N-(1-Zn)(3). The binding constants of the longer ligand (C(60)-l-Tripod) and the pyromellitdiimide ligand (PI-Tripod) are almost the same as those without the fullerene or pyromellitdiimide groups, indicating that they interact via three pyridyl groups to the porphyrinatozinc(II) coordination. In contrast, the larger binding constants and the almost complete fluorescence quenching in the case of the shorter ligand (C(60)-s-Tripod) indicate that the interaction with N-(1-Zn)(3) is via two pyridyl groups to the porphyrinatozinc(II) coordination and a pi-pi interaction of the fullerene to the porphyrin(s). The fluorescence of N-(1-Zn)(3) was quenched by up to 80% by the interaction of C(60)-l-Tripod. The nanosecond transient absorption spectra showed only the excited triplet peak of the fullerene on selective excitation of the macrocyclic porphyrins, indicating that energy transfer from the excited N-(1-Zn)(3) group to the fullerenyl moiety occurs in the C(60)-l-Tripod/N-(1-Zn)(3) composite. In the case of PI-Tripod, the fluorescence of N-(1-Zn)(3) was quenched by 45%. It seems that the fluorescence quenching probably originates from electron transfer from the excited N-(1-Zn)(3) group to the pyromellitdiimide moiety.

  DOI：

  10.1021/ic201250q