2,5-diacetoxymercuro-3,4-ethylenedioxythiophene | 640737-73-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-diacetoxymercuro-3,4-ethylenedioxythiophene
• CAS: 640737-73-1
• 化学式: C₁₀H₁₀Hg₂O₆S
• 分子量: 659.432
• InChiKey: DWDXLPYXRRJZDT-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -0.11
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2,5-diacetoxymercuro-3,4-ethylenedioxythiophene 在 碘 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以55%的产率得到2,5-diiodo-3,4-ethylenedioxythiophene
  参考文献：
  名称：

  Solid-State Synthesis of a Conducting Polythiophene via an Unprecedented Heterocyclic Coupling Reaction

  摘要：

  Prolonged storage (similar to2 years) or gentle heating (50-80 degreesC) of crystalline 2,5-dibromo-3,4-ethylenedioxythiophene (DBEDOT) affords a highly conducting, bromine-doped poly(3,4-ethylenedioxythiophene) (PEDOT), as confirmed by solid-state NMR, FTIR, CV, and vis-NIR spectroscopies. The novel solid-state polymerization (SSP) does not occur for 2,5-dichloro-3,4-ethylenedioxythiophene (DCEDOT), and requires a much higher temperature (>130 degreesC) for 2,5-diiodo-3,4-ethylenedioxythiophene (DIEDOT). X-ray structural analysis of the above dihalothiophenes reveals short Hal...Hal distances between adjacent molecules in DBEDOT and DIEDOT, but not in DCEDOT. The polymerization may also occur in the melt but is significantly slower and leads to poorly conductive material. Detailed studies of the reaction were performed using ESR, DSC, microscopy, and gravimetric analyses. SSP starts on crystal defect sites; it is exothermic by 14 kcal/mol and requires activation energy of similar to26 kcal/mol (for DBEDOT). The temperature dependence of the conductivity of SSP-PEDOT (sigma(rt) = 20-80 S/cm) reveals a slight thermal activation. It can be further increased by a factor of 2 by doping with iodine. Using this approach, thin films of PEDOT with conductivity as high as 20 S/cm were fabricated on insulating flexible plastic surfaces.

  DOI：

  10.1021/ja037115y
• 作为产物：
  描述：

  mercury(II) diacetate 、 3,4-乙烯二氧噻吩 以 溶剂黄146 为溶剂， 以95%的产率得到2,5-diacetoxymercuro-3,4-ethylenedioxythiophene
  参考文献：
  名称：

  Solid-State Synthesis of a Conducting Polythiophene via an Unprecedented Heterocyclic Coupling Reaction

  摘要：

  Prolonged storage (similar to2 years) or gentle heating (50-80 degreesC) of crystalline 2,5-dibromo-3,4-ethylenedioxythiophene (DBEDOT) affords a highly conducting, bromine-doped poly(3,4-ethylenedioxythiophene) (PEDOT), as confirmed by solid-state NMR, FTIR, CV, and vis-NIR spectroscopies. The novel solid-state polymerization (SSP) does not occur for 2,5-dichloro-3,4-ethylenedioxythiophene (DCEDOT), and requires a much higher temperature (>130 degreesC) for 2,5-diiodo-3,4-ethylenedioxythiophene (DIEDOT). X-ray structural analysis of the above dihalothiophenes reveals short Hal...Hal distances between adjacent molecules in DBEDOT and DIEDOT, but not in DCEDOT. The polymerization may also occur in the melt but is significantly slower and leads to poorly conductive material. Detailed studies of the reaction were performed using ESR, DSC, microscopy, and gravimetric analyses. SSP starts on crystal defect sites; it is exothermic by 14 kcal/mol and requires activation energy of similar to26 kcal/mol (for DBEDOT). The temperature dependence of the conductivity of SSP-PEDOT (sigma(rt) = 20-80 S/cm) reveals a slight thermal activation. It can be further increased by a factor of 2 by doping with iodine. Using this approach, thin films of PEDOT with conductivity as high as 20 S/cm were fabricated on insulating flexible plastic surfaces.

  DOI：

  10.1021/ja037115y