tetraethyl 2,5-bis(methanephosphonate)pyridine | 1254709-20-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: tetraethyl 2,5-bis(methanephosphonate)pyridine
• 英文别名: 2,5-Bis[[diethoxy(oxido)phosphaniumyl]methyl]pyridine；2,5-bis[[diethoxy(oxido)phosphaniumyl]methyl]pyridine
• CAS: 1254709-20-0
• 化学式: C₁₅H₂₇NO₆P₂
• 分子量: 379.33
• InChiKey: UOJMMCRTRJBVRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  95.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tetraethyl 2,5-bis(methanephosphonate)pyridine 、 3,4-乙撑基二氧甲醛噻吩 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 2,5-bis[2-(3,4-ethylenedioxythien-2-yl)-ethen-1-yl]pyridine
  参考文献：
  名称：

  Pyridine−EDOT Heteroarylene−Vinylene Donor−Acceptor Polymers

  摘要：

  Two heteroarylene-vinylene donor acceptor polymers, P(2,6-Py-V-EDOT) and P(2,5-Py-V-EDOT), containing vinylene-spaced simple donor (EDOT) and acceptor (pyridine) moieties, are presented. The central pyridine ring of the repeating unit is either 2,6- or 2,5-substituted, leading to different structural and electronic properties of the monomers. Polymers were obtained by either oxidative electropolymerization or Yamamoto coupling and fully characterized by NMR, UV-vis absorption, GPC, TGA, DSC, electrochemistry, and spectroelectrochemistry. Detailed ab initio computations have been performed for the monomers and model oligomers for analyzing their optical and electronic properties. GPC showed that isolated polymers obtained via Yamamoto poly coupling have low molecular weights, likely due to solubility issues. The electrochemical polymerizations led to p- and n-dopable polymers, with 2,5-Py-V-EDOT yielding more reversible n-doped process. The energetic positions revealed HOMO (-5.1 and -5.0 eV), LUMO (-3.4 eV), and narrow bandgap (1.6 and 1.7 eV) energies closely matching materials-design rules for optimized organic photovoltaic devices. Preliminary investigation in photovoltaic devices in combination with C-71-PCBM afforded relatively modest power conversion efficiencies of similar to 0.5% (AM 1.5G, 100 mW/cm(2)), which were attributed to the low molecular-weight of the polymers accessible via the chemical route.

  DOI：

  10.1021/ma1017132
• 作为产物：
  描述：

  2,5-二(溴甲基)吡啶 、 亚磷酸三乙酯 反应 3.0h， 以91%的产率得到tetraethyl 2,5-bis(methanephosphonate)pyridine
  参考文献：
  名称：

  Pyridine−EDOT Heteroarylene−Vinylene Donor−Acceptor Polymers

  摘要：

  Two heteroarylene-vinylene donor acceptor polymers, P(2,6-Py-V-EDOT) and P(2,5-Py-V-EDOT), containing vinylene-spaced simple donor (EDOT) and acceptor (pyridine) moieties, are presented. The central pyridine ring of the repeating unit is either 2,6- or 2,5-substituted, leading to different structural and electronic properties of the monomers. Polymers were obtained by either oxidative electropolymerization or Yamamoto coupling and fully characterized by NMR, UV-vis absorption, GPC, TGA, DSC, electrochemistry, and spectroelectrochemistry. Detailed ab initio computations have been performed for the monomers and model oligomers for analyzing their optical and electronic properties. GPC showed that isolated polymers obtained via Yamamoto poly coupling have low molecular weights, likely due to solubility issues. The electrochemical polymerizations led to p- and n-dopable polymers, with 2,5-Py-V-EDOT yielding more reversible n-doped process. The energetic positions revealed HOMO (-5.1 and -5.0 eV), LUMO (-3.4 eV), and narrow bandgap (1.6 and 1.7 eV) energies closely matching materials-design rules for optimized organic photovoltaic devices. Preliminary investigation in photovoltaic devices in combination with C-71-PCBM afforded relatively modest power conversion efficiencies of similar to 0.5% (AM 1.5G, 100 mW/cm(2)), which were attributed to the low molecular-weight of the polymers accessible via the chemical route.

  DOI：

  10.1021/ma1017132

文献信息

• Pyridine−EDOT Heteroarylene−Vinylene Donor−Acceptor Polymers
  作者：Alessandro Abbotto、Erika Herrera Calderon、Milind S. Dangate、Filippo De Angelis、Norberto Manfredi、Claudio Maria Mari、Chiara Marinzi、Edoardo Mosconi、Michele Muccini、Riccardo Ruffo、Mirko Seri

  DOI：10.1021/ma1017132

  日期：2010.12.14

  Two heteroarylene-vinylene donor acceptor polymers, P(2,6-Py-V-EDOT) and P(2,5-Py-V-EDOT), containing vinylene-spaced simple donor (EDOT) and acceptor (pyridine) moieties, are presented. The central pyridine ring of the repeating unit is either 2,6- or 2,5-substituted, leading to different structural and electronic properties of the monomers. Polymers were obtained by either oxidative electropolymerization or Yamamoto coupling and fully characterized by NMR, UV-vis absorption, GPC, TGA, DSC, electrochemistry, and spectroelectrochemistry. Detailed ab initio computations have been performed for the monomers and model oligomers for analyzing their optical and electronic properties. GPC showed that isolated polymers obtained via Yamamoto poly coupling have low molecular weights, likely due to solubility issues. The electrochemical polymerizations led to p- and n-dopable polymers, with 2,5-Py-V-EDOT yielding more reversible n-doped process. The energetic positions revealed HOMO (-5.1 and -5.0 eV), LUMO (-3.4 eV), and narrow bandgap (1.6 and 1.7 eV) energies closely matching materials-design rules for optimized organic photovoltaic devices. Preliminary investigation in photovoltaic devices in combination with C-71-PCBM afforded relatively modest power conversion efficiencies of similar to 0.5% (AM 1.5G, 100 mW/cm(2)), which were attributed to the low molecular-weight of the polymers accessible via the chemical route.