1,4-diiodo-2,3,5,6-tetramethoxybenzene | 54812-45-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,4-diiodo-2,3,5,6-tetramethoxybenzene
• 英文别名: 1,4-diiodo-2,3,5,6-tetramethoxy-benzene；1,4-Dijod-2,3,5,6-tetramethoxy-benzol；3,6-Diiod-1,2,4,5-tetramethoxybenzol；1,4-Diiodo-2,3,5,6-tetramethoxybenzene
• CAS: 54812-45-2
• 化学式: C₁₀H₁₂I₂O₄
• 分子量: 450.012
• InChiKey: IHJQZTLDSJPWKT-UHFFFAOYSA-N

物化性质

• 熔点：
  136-137 °C(Solv: methanol (67-56-1))
• 沸点：
  451.9±45.0 °C(Predicted)
• 密度：
  1.960±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-diiodo-2,3,5,6-tetramethoxybenzene 在 氢溴酸 、 铜 、 溶剂黄146 作用下， 生成 7,14-dimethoxy-benz[c]isochromeno[3,4-g]chromene-5,12-dione
  参考文献：
  名称：

  Nilson, Acta Chemica Scandinavica (1947), 1956, vol. 10, p. 1377,1379

  摘要：

  DOI：
• 作为产物：
  描述：

  2,5-二羟基-1,4-苯喹酮 在 sodium tetrahydroborate 、 正丁基锂 、 四甲基乙二胺 、 碘 、 sodium hydrogensulfite 、 potassium hydroxide 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 生成 1,4-diiodo-2,3,5,6-tetramethoxybenzene
  参考文献：
  名称：

  Tetramethoxybenzene is a Good Building Block for Molecular Wires: Insights from Photoinduced Electron Transfer

  摘要：

  Two donor bridge-acceptor molecules with terminal triarylamine and Ru(bpy)(3)(2+) (bpy = 2,2'-bipyridine) redox partners were synthesized and investigated by cyclic voltammetry, optical absorption, luminescence, and transient absorption spectroscopy. The two dyads differ only by the central bridging unit, which was tetramethoxybenzene (tmb) in one case and unsubstituted phenylene (ph) in the other case. Photoirradiation of the Ru(bpy)(3)(2+) complex of the two dyads triggers intramolecular electron transfer from the triarylamine to the (MLCT)-M-3-excited metal complex, and this process occurs with time constants of 1.5 and 6.8 ns for the tmb- and ph-bridged dyads, respectively. Thermal electron transfer in the reverse direction then leads to disappearance of the photoproduct with a time constant of 10 ns in both dyads. The faster rate of photoinduced charge transfer in the tmb-bridged dyad can be understood in the framework of a hole-tunneling model in which the electron-rich tmb bridge imposes a more shallow barrier than the less electron-rich ph spacer. Until now tmb-based molecular wires have received very little attention, and alkoxy substituents have been mostly used for improving the solubility of oligo-p-phenylene vinylene (OPV) and oligo-p-phenylene ethynylene (OPE) wires. Our study illustrates how four alkoxy-substituents on a phenylene backbone can have a significant influence on the charge-transfer properties of a molecular wire, and this is relevant in the greater context of a future molecular electronics technology.

  DOI：

  10.1021/acs.jpca.5b03649

文献信息

• Staab, Heinz A.; Weiser, Juergen; Futscher, Michael, Chemische Berichte, 1992, vol. 125, # 10, p. 2285 - 2302
  作者：Staab, Heinz A.、Weiser, Juergen、Futscher, Michael、Voit, Guido、Rueckemann, Andreas、Anders, Christine

  DOI：——

  日期：——
• Transition metal free coupling of highly fluorinated and non-fluorinated pi-electron systems
  申请人：Watson Mark D.

  公开号：US20080042127A1

  公开（公告）日：2008-02-21

  A method for making an organic conjugated monomer, oligomer, polymer or small molecule includes reacting a silyl substituted pi-system compound with a highly fluorinated pi-system compound.
• Tetramethoxybenzene is a Good Building Block for Molecular Wires: Insights from Photoinduced Electron Transfer
  作者：Luisa G. Heinz、Oleksandr Yushchenko、Markus Neuburger、Eric Vauthey、Oliver S. Wenger

  DOI：10.1021/acs.jpca.5b03649

  日期：2015.6.4

  Two donor bridge-acceptor molecules with terminal triarylamine and Ru(bpy)(3)(2+) (bpy = 2,2'-bipyridine) redox partners were synthesized and investigated by cyclic voltammetry, optical absorption, luminescence, and transient absorption spectroscopy. The two dyads differ only by the central bridging unit, which was tetramethoxybenzene (tmb) in one case and unsubstituted phenylene (ph) in the other case. Photoirradiation of the Ru(bpy)(3)(2+) complex of the two dyads triggers intramolecular electron transfer from the triarylamine to the (MLCT)-M-3-excited metal complex, and this process occurs with time constants of 1.5 and 6.8 ns for the tmb- and ph-bridged dyads, respectively. Thermal electron transfer in the reverse direction then leads to disappearance of the photoproduct with a time constant of 10 ns in both dyads. The faster rate of photoinduced charge transfer in the tmb-bridged dyad can be understood in the framework of a hole-tunneling model in which the electron-rich tmb bridge imposes a more shallow barrier than the less electron-rich ph spacer. Until now tmb-based molecular wires have received very little attention, and alkoxy substituents have been mostly used for improving the solubility of oligo-p-phenylene vinylene (OPV) and oligo-p-phenylene ethynylene (OPE) wires. Our study illustrates how four alkoxy-substituents on a phenylene backbone can have a significant influence on the charge-transfer properties of a molecular wire, and this is relevant in the greater context of a future molecular electronics technology.
• Nilson, Acta Chemica Scandinavica (1947), 1956, vol. 10, p. 1377,1379
  作者：Nilson

  DOI：——

  日期：——