5,5'-di(4-[diethoxyphosphorylmethyl]phenyl)-2,2'-[p-(2,5-bis{hexyloxy}phenylene)]-bis(1,3,4-oxadiazole) | 611610-39-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,5'-di(4-[diethoxyphosphorylmethyl]phenyl)-2,2'-[p-(2,5-bis{hexyloxy}phenylene)]-bis(1,3,4-oxadiazole)
• 英文别名: 2-[4-[[Diethoxy(oxido)phosphaniumyl]methyl]phenyl]-5-[4-[5-[4-[[diethoxy(oxido)phosphaniumyl]methyl]phenyl]-1,3,4-oxadiazol-2-yl]-2,5-dihexoxyphenyl]-1,3,4-oxadiazole；2-[4-[[diethoxy(oxido)phosphaniumyl]methyl]phenyl]-5-[4-[5-[4-[[diethoxy(oxido)phosphaniumyl]methyl]phenyl]-1,3,4-oxadiazol-2-yl]-2,5-dihexoxyphenyl]-1,3,4-oxadiazole
• CAS: 611610-39-0
• 化学式: C₄₄H₆₀N₄O₁₀P₂
• 分子量: 866.929
• InChiKey: VFCDVNJQIXVWLC-UHFFFAOYSA-N

物化性质

• 沸点：
  918.9±75.0 °C(predicted)
• 密度：
  1.170±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  60
• 可旋转键数：
  28
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  179
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  2,5-二羟基对苯二甲酸乙酯 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 一水合肼 、 potassium iodide 、 三氯氧磷 作用下， 以 N-甲基吡咯烷酮 、 乙醇 、 环己酮 、 苯 为溶剂， 反应 57.5h， 生成 5,5'-di(4-[diethoxyphosphorylmethyl]phenyl)-2,2'-[p-(2,5-bis{hexyloxy}phenylene)]-bis(1,3,4-oxadiazole)
  参考文献：
  名称：

  Synthesis and Optically Acid-Sensory and Electrochemical Properties of Novel Polyoxadiazole Derivatives

  摘要：

  A series of PPV-based polyoxadiazoles have been synthesized by Homer and Suzuki coupling polymerization to investigate their structure-property relationship. These copolymers exhibit good thermal stability (decomposition temperature around 352-413 degreesC). Excimer formation in P4-P9 was confirmed by their absorption and PL spectral peak transition in solution at different concentrations and in thin films. Unusual absorption and fluorescence were observed in acid media and have been related to photoinduced charge transfer in alternating donor-acceptor architecture. The photoinduced charge transfer led to a blue shift in iminodibenzyl-containing copolymers (P1-P3) and a red shift in fluorene-containing copolymers (P9), reflecting the fact that iminodibenzyl is a stronger electron-donating unit. The electrochemical properties of the copolymers were evaluated by cyclic voltammetry and their highest occupied molecular orbital and the lowest unoccupied molecular orbit energy levels were estimated. The optical band gaps of the dioxadiazole-containing copolymers show great discrepancy with the electrochemical band gap energy due to the donor-acceptor feature of the dioxadiazole unit.

  DOI：

  10.1021/ma035576y

文献信息

• Synthesis and Optically Acid-Sensory and Electrochemical Properties of Novel Polyoxadiazole Derivatives
  作者：Tzi-Yi Wu、Rong-Bin Sheu、Yun Chen

  DOI：10.1021/ma035576y

  日期：2004.2.1

  A series of PPV-based polyoxadiazoles have been synthesized by Homer and Suzuki coupling polymerization to investigate their structure-property relationship. These copolymers exhibit good thermal stability (decomposition temperature around 352-413 degreesC). Excimer formation in P4-P9 was confirmed by their absorption and PL spectral peak transition in solution at different concentrations and in thin films. Unusual absorption and fluorescence were observed in acid media and have been related to photoinduced charge transfer in alternating donor-acceptor architecture. The photoinduced charge transfer led to a blue shift in iminodibenzyl-containing copolymers (P1-P3) and a red shift in fluorene-containing copolymers (P9), reflecting the fact that iminodibenzyl is a stronger electron-donating unit. The electrochemical properties of the copolymers were evaluated by cyclic voltammetry and their highest occupied molecular orbital and the lowest unoccupied molecular orbit energy levels were estimated. The optical band gaps of the dioxadiazole-containing copolymers show great discrepancy with the electrochemical band gap energy due to the donor-acceptor feature of the dioxadiazole unit.