6,11-Dihexoxy-3-methoxytriphenylen-2-ol | 1133161-16-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 6,11-Dihexoxy-3-methoxytriphenylen-2-ol
• 英文别名: 6,11-dihexoxy-3-methoxytriphenylen-2-ol
• CAS: 1133161-16-6
• 化学式: C₃₁H₃₈O₄
• 分子量: 474.64
• InChiKey: HZGMGVAOQFZBEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,11-Dihexoxy-3-methoxytriphenylen-2-ol 、 1,7-二溴代苝二酰亚胺 在 18-冠醚-6 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以42%的产率得到POG0
  参考文献：
  名称：

  Synthesis and Optical Properties of Triphenylene-Based Dendritic Donor Perylene Diimide Acceptor Systems

  摘要：

  A donor-acceptor charge transfer system based on two discotic mesogens has been synthesized. The donor is either a triphenylene (POG0) or a triphenylene-based conjugated dendron (POG1), while the acceptor is a perylene diimide (PDI) core. The donors are covalently linked to the bay positions of the PDI core through an ether linkage. In chloroform, due to the short donor-acceptor distance and the matching frontier orbital levels, photoinduced charge transfer from either the donor excitation or the acceptor excitation are both thermodynamically and kinetically favored, resulting in efficient quenching of both donor and acceptor fluorescence. In a less polar solvent, hexane, while charge transfer is still the dominant mechanism for decay of the excited electronic state of POG1, photo induced charge transfer is no longer energetically favorable for POG0 when the acceptor PDI core is excited, making the PDI core of POG0 weakly fluorescent in chloroform but strongly so in hexane. In solid film, POGO is highly aggregated through both PDI-PDI and triphenylene-triphenylene homotopic stacking. POG1, on the other hand, aggregates through triphenylene dendrons with limited PDI-PDI core stacking, presumably due to the steric hindrance caused by bulky triphenylene moieties which block the access to the PDI core. The efficient photoinduced charge transfer, coupled with the homotopic stacking that forms separated electron-transporting PDI-stacked columns and hole transporting triphenylene-stacked columns, suggests that the reported donor-acceptor systems based on dual-discotic mesogens are potentially new efficient photovoltaic materials.

  DOI：

  10.1021/jp1085334

文献信息

• Synthesis and optical properties of triphenylene-based conjugated dendrons
  作者：Mahuya Bagui、Joseph S. Melinger、Sanjiban Chakraborty、J. Andrew Keightley、Zhonghua Peng

  DOI：10.1016/j.tet.2008.12.017

  日期：2009.2

  Conjugated dendrons based on triphenylene building blocks have been synthesized. Such dendrons exhibit broader absorption wavelength range and higher absorption coefficients than their phenyl analogs. They also possess extended excited state lifetimes and high fluorescence quantum yields in dilute Solutions. In the solid state, these dendrons are highly aggregated, resulting in significantly broadened and red-shifted emissions, whose decay transients depend strongly on the detection wavelength. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and Optical Properties of Triphenylene-Based Dendritic Donor Perylene Diimide Acceptor Systems
  作者：Mahuya Bagui、Tanmoy Dutta、Sanjiban Chakraborty、Joseph S. Melinger、Haizhen Zhong、Andrew Keightley、Zhonghua Peng

  DOI：10.1021/jp1085334

  日期：2011.3.10

  A donor-acceptor charge transfer system based on two discotic mesogens has been synthesized. The donor is either a triphenylene (POG0) or a triphenylene-based conjugated dendron (POG1), while the acceptor is a perylene diimide (PDI) core. The donors are covalently linked to the bay positions of the PDI core through an ether linkage. In chloroform, due to the short donor-acceptor distance and the matching frontier orbital levels, photoinduced charge transfer from either the donor excitation or the acceptor excitation are both thermodynamically and kinetically favored, resulting in efficient quenching of both donor and acceptor fluorescence. In a less polar solvent, hexane, while charge transfer is still the dominant mechanism for decay of the excited electronic state of POG1, photo induced charge transfer is no longer energetically favorable for POG0 when the acceptor PDI core is excited, making the PDI core of POG0 weakly fluorescent in chloroform but strongly so in hexane. In solid film, POGO is highly aggregated through both PDI-PDI and triphenylene-triphenylene homotopic stacking. POG1, on the other hand, aggregates through triphenylene dendrons with limited PDI-PDI core stacking, presumably due to the steric hindrance caused by bulky triphenylene moieties which block the access to the PDI core. The efficient photoinduced charge transfer, coupled with the homotopic stacking that forms separated electron-transporting PDI-stacked columns and hole transporting triphenylene-stacked columns, suggests that the reported donor-acceptor systems based on dual-discotic mesogens are potentially new efficient photovoltaic materials.