9-(4-(6-bromo-3,8-dioctylpyren-1-yl)phenyl)-5,12-bis(3,5-di-tert-butylphenoxy)-1H-isochromeno[6',5',4':10,5,6]anthra[2,1,9-def]isoquinoline-1,3,8,10(9H)-tetraone | 1185354-53-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 9-(4-(6-bromo-3,8-dioctylpyren-1-yl)phenyl)-5,12-bis(3,5-di-tert-butylphenoxy)-1H-isochromeno[6',5',4':10,5,6]anthra[2,1,9-def]isoquinoline-1,3,8,10(9H)-tetraone
• CAS: 1185354-53-3
• 化学式: C₉₀H₉₂BrNO₇
• 分子量: 1379.63
• InChiKey: LRQXTTOBSRXCRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  25.76
• 重原子数：
  99.0
• 可旋转键数：
  20.0
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  99.21
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-乙基己胺 、 9-(4-(6-bromo-3,8-dioctylpyren-1-yl)phenyl)-5,12-bis(3,5-di-tert-butylphenoxy)-1H-isochromeno[6',5',4':10,5,6]anthra[2,1,9-def]isoquinoline-1,3,8,10(9H)-tetraone 在 吡啶 作用下， 以87%的产率得到N-(2-ethylhexyl)-1,7-bis(3,5-di-t-butylphenoxy)perylene(3,4:9,10)dicarboximidedicarboxyanhydride
  参考文献：
  名称：

  Photoinitiated Charge Transport through π-Stacked Electron Conduits in Supramolecular Ordered Assemblies of Donor−Acceptor Triads

  摘要：

  Photochemical electron donor-acceptor triads having an aminopyrene primary donor (APy) and a p-diaminobenzene secondary donor (DAB) attached to either one or both imide nitrogen atoms of a perylene-3,4:9,10-bis(dicarboximide) (PDI) electron acceptor were prepared to give DAB-APy-PDI and DAB-APy-PDI-APy-DAB. In toluene, both triads are monomeric, but in methylcyclohexane, they self-assemble into ordered helical heptamers and hexamers, respectively, in which the PDI molecules are pi-stacked in a columnar fashion, as evidenced by small- and wide-angle X-ray scattering. Photoexcitation of these supramolecular assemblies results in rapid formation of DAB(+center dot)-PDI-center dot spin-polarized radical ion pairs having spin-spin dipolar interactions, which show that the average distance between the two radical ions is much larger in the assemblies (31 angstrom) than it is in their monomeric building blocks (23 angstrom). This work demonstrates that electron hopping through the pi-stacked PDI molecules is fast enough to compete effectively with charge recombination (40 ns) in these systems, making these materials of interest as photoactive assemblies for artificial photosynthesis and organic photovoltaics.

  DOI：

  10.1021/ja903903q
• 作为产物：
  描述：

  4-(6-bromo-3,8-dioctylpyren-1-yl)aniline 、 1,7-(3',5'-di-t-butylphenoxy)perylene-3,4:9,10-tetracarboxyanhydride 在 吡啶 作用下， 反应 72.0h， 以19%的产率得到9-(4-(6-bromo-3,8-dioctylpyren-1-yl)phenyl)-5,12-bis(3,5-di-tert-butylphenoxy)-1H-isochromeno[6',5',4':10,5,6]anthra[2,1,9-def]isoquinoline-1,3,8,10(9H)-tetraone
  参考文献：
  名称：

  Photoinitiated Charge Transport through π-Stacked Electron Conduits in Supramolecular Ordered Assemblies of Donor−Acceptor Triads

  摘要：

  Photochemical electron donor-acceptor triads having an aminopyrene primary donor (APy) and a p-diaminobenzene secondary donor (DAB) attached to either one or both imide nitrogen atoms of a perylene-3,4:9,10-bis(dicarboximide) (PDI) electron acceptor were prepared to give DAB-APy-PDI and DAB-APy-PDI-APy-DAB. In toluene, both triads are monomeric, but in methylcyclohexane, they self-assemble into ordered helical heptamers and hexamers, respectively, in which the PDI molecules are pi-stacked in a columnar fashion, as evidenced by small- and wide-angle X-ray scattering. Photoexcitation of these supramolecular assemblies results in rapid formation of DAB(+center dot)-PDI-center dot spin-polarized radical ion pairs having spin-spin dipolar interactions, which show that the average distance between the two radical ions is much larger in the assemblies (31 angstrom) than it is in their monomeric building blocks (23 angstrom). This work demonstrates that electron hopping through the pi-stacked PDI molecules is fast enough to compete effectively with charge recombination (40 ns) in these systems, making these materials of interest as photoactive assemblies for artificial photosynthesis and organic photovoltaics.

  DOI：

  10.1021/ja903903q