1-(6-nitro-2-methyl-1-benzothiophen-3-yl)-2-(6'-iodo-2'-methyl-1'-benzothiophen-3'-yl)hexafluorocyclopentene | 905583-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 1-(6-nitro-2-methyl-1-benzothiophen-3-yl)-2-(6'-iodo-2'-methyl-1'-benzothiophen-3'-yl)hexafluorocyclopentene
• 英文别名: 3-[3,3,4,4,5,5-Hexafluoro-2-(6-iodo-2-methyl-1-benzothiophen-3-yl)cyclopenten-1-yl]-2-methyl-6-nitro-1-benzothiophene
• CAS: 905583-68-8
• 化学式: C₂₃H₁₂F₆INO₂S₂
• 分子量: 639.381
• InChiKey: JIUABYDSGHZYMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-(6-nitro-2-methyl-1-benzothiophen-3-yl)-2-(6'-iodo-2'-methyl-1'-benzothiophen-3'-yl)hexafluorocyclopentene 、 3,4-乙烯二氧噻吩 在 bis-triphenylphosphine-palladium(II) chloride 正丁基锂 、 四甲基乙二胺 、 三丁基氯化锡 作用下， 以 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 24.17h， 生成 1-[6-(3',4'-ethylenedioxy)thienyl]-2-methyl-1-benzothiophen-3-yl-2-[6'-nitro-2'-methyl-1'-benzothiophen-3'-yl]hexafluorocyclopentene
  参考文献：
  名称：

  Diarylethenes with intramolecular donor–acceptor structures for photo-induced electrochemical change

  摘要：

  Diarylethenes with donor-acceptor groups were synthesized to induce electrochemical switching by light. Photoisomerization was induced by 1,2-bis(2-methyl-1-benzo[b]thiophen-3-yl)perfluorocyclopentene (BTF, 1) unit, while the 3,4-ethylenedioxythiophene (T) and nitro (N) groups were directly connected to BTF, to extend pi-electron delocalization. Spectral change to a longer wavelength through photochromism was significant in the donor-acceptor structures (6), accompanied by an increase in the molar absorption coefficients, than those of the unsubstituted BTF (1) or the BTF substituted with only acceptor group (2c and 3c). A significant peak shift toward lower redox energy was observed when the molecules were converted from an open isomer to a closed isomer. The plot of the reduction potentials (E-1/2(red), V vs Ag/AgCl) vs LUMO energy eV) for the diarylethenes indicates that the reduction potential is strongly dependent on the nature of the substituents around the diarylethene unit. When 6 was applied to a photocell of Au/PC/ITO glass, in which PC is the polystyrene containing 6, it became possible to switch the conductivity of the cell through the film by UV-vis irradiation, as estimated by the I-V plot on a photocell. The conductivity of the cell exposed to UV light was three times larger than that of the cell exposed to visible light, and 10 times larger than that of the cell containing 3, indicating the importance of the push-pull structure for pi-electron connectivity through the donor-BTF-acceptor. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.089
• 作为产物：
  描述：

  1-[6-nitro-2-methyl-1-benzothiophen-3-yl]-2-(2'-methyl-1'-benzothiophen-3'-yl)hexafluorocyclopentene 在 硫酸 、 碘 、 高碘酸 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 以85%的产率得到1-(6-nitro-2-methyl-1-benzothiophen-3-yl)-2-(6'-iodo-2'-methyl-1'-benzothiophen-3'-yl)hexafluorocyclopentene
  参考文献：
  名称：

  Diarylethenes with intramolecular donor–acceptor structures for photo-induced electrochemical change

  摘要：

  Diarylethenes with donor-acceptor groups were synthesized to induce electrochemical switching by light. Photoisomerization was induced by 1,2-bis(2-methyl-1-benzo[b]thiophen-3-yl)perfluorocyclopentene (BTF, 1) unit, while the 3,4-ethylenedioxythiophene (T) and nitro (N) groups were directly connected to BTF, to extend pi-electron delocalization. Spectral change to a longer wavelength through photochromism was significant in the donor-acceptor structures (6), accompanied by an increase in the molar absorption coefficients, than those of the unsubstituted BTF (1) or the BTF substituted with only acceptor group (2c and 3c). A significant peak shift toward lower redox energy was observed when the molecules were converted from an open isomer to a closed isomer. The plot of the reduction potentials (E-1/2(red), V vs Ag/AgCl) vs LUMO energy eV) for the diarylethenes indicates that the reduction potential is strongly dependent on the nature of the substituents around the diarylethene unit. When 6 was applied to a photocell of Au/PC/ITO glass, in which PC is the polystyrene containing 6, it became possible to switch the conductivity of the cell through the film by UV-vis irradiation, as estimated by the I-V plot on a photocell. The conductivity of the cell exposed to UV light was three times larger than that of the cell exposed to visible light, and 10 times larger than that of the cell containing 3, indicating the importance of the push-pull structure for pi-electron connectivity through the donor-BTF-acceptor. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.089