(5-{2-[4-(5,5-dimethyl-[1,3]dioxan-2-yl)-2,5-dipropoxy-phenyl]-vinyl}-thiophen-2-ylmethyl)-phosphonic acid diethyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (5-{2-[4-(5,5-dimethyl-[1,3]dioxan-2-yl)-2,5-dipropoxy-phenyl]-vinyl}-thiophen-2-ylmethyl)-phosphonic acid diethyl ester
• 英文别名: (5-{2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropoxy-phenyl]vinyl}thiophen-2-ylmethyl)phosphonic acid diethyl ester；2-[4-[(E)-2-[5-(diethoxyphosphorylmethyl)thiophen-2-yl]ethenyl]-2,5-dipropoxyphenyl]-5,5-dimethyl-1,3-dioxane
• 化学式: C₂₉H₄₃O₇PS
• 分子量: 566.696
• InChiKey: BIPVPRATJALUNF-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (5-{2-[4-(5,5-dimethyl-[1,3]dioxan-2-yl)-2,5-dipropoxy-phenyl]-vinyl}-thiophen-2-ylmethyl)-phosphonic acid diethyl ester 在 盐酸 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 4-(2-{5-[2-(4-methoxyphenyl)vinyl]thiophen-2-yl}vinyl)-2,5-dipropoxybenzaldehyde
  参考文献：
  名称：

  Stepwise Unidirectional Synthesis of Oligo Phenylene Vinylenes with a Series of Monomers. Use in Plastic Solar Cells

  摘要：

  Four new monomers for directional stepwise synthesis of oligophenylenevinylenes (OPVs) (4-{2[4-(5,5-dimethyl [1,31 dioxan-2-yl)-2,5-dipropoxyphenyl] vinyl }benzyl)phosphonic acid diethyl ester, (5-{2- [4-(5,5-dimethyl [1,31 dioxan-2-yl)-2,5-dipropylphenyl] vinyl }thiophene-2-yl-methyl)phosphonic acid diethyl ester, (5-{2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropoxyphenyl]vinyl}thiophene-2-yl-methyl)phosphonic acid diethyl ester, and (7-{2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropylphenyl]-vinyl}benzo[1,2,5]thiadiazol-4-ylmethyl)phosphonic acid diethyl ester have been prepared. Trimeric OPVs were then synthesized and tested as active materials in photovoltaic cells. Conversion efficiencies in the range of 0.5-1% were obtained in blends with the soluble C-60 derivative PCBM. A terpyridine end-functionalized trimer and a heterotrimer with a mixed composition of monomers were also prepared.

  DOI：

  10.1021/jo0506783
• 作为产物：
  描述：

  2-(噻吩甲基)膦酸二乙酯 在 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (5-{2-[4-(5,5-dimethyl-[1,3]dioxan-2-yl)-2,5-dipropoxy-phenyl]-vinyl}-thiophen-2-ylmethyl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  Stepwise Unidirectional Synthesis of Oligo Phenylene Vinylenes with a Series of Monomers. Use in Plastic Solar Cells

  摘要：

  Four new monomers for directional stepwise synthesis of oligophenylenevinylenes (OPVs) (4-{2[4-(5,5-dimethyl [1,31 dioxan-2-yl)-2,5-dipropoxyphenyl] vinyl }benzyl)phosphonic acid diethyl ester, (5-{2- [4-(5,5-dimethyl [1,31 dioxan-2-yl)-2,5-dipropylphenyl] vinyl }thiophene-2-yl-methyl)phosphonic acid diethyl ester, (5-{2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropoxyphenyl]vinyl}thiophene-2-yl-methyl)phosphonic acid diethyl ester, and (7-{2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropylphenyl]-vinyl}benzo[1,2,5]thiadiazol-4-ylmethyl)phosphonic acid diethyl ester have been prepared. Trimeric OPVs were then synthesized and tested as active materials in photovoltaic cells. Conversion efficiencies in the range of 0.5-1% were obtained in blends with the soluble C-60 derivative PCBM. A terpyridine end-functionalized trimer and a heterotrimer with a mixed composition of monomers were also prepared.

  DOI：

  10.1021/jo0506783

文献信息

• Synthesis of an All-in-One Molecule (for Organic Solar Cells)
  作者：Ole Hagemann、Mikkel Jørgensen、Frederik C. Krebs

  DOI：10.1021/jo060491r

  日期：2006.7.1

  functionalities needed for solar cell action from light harvesting, carrier generation, and separation, to transport and contact to external electrodes. A convergent synthetic strategy with some 60 steps involving preparation of regioregular oligothiophenes, a zinc porphyrin, a bisterpyridine ruthenium(II) complex, a hetero oligo phenylenevinylene and functional end groups is described. Preliminary

  已经制备了在有机太阳能电池领域中具有应用的多域化合物。这种多合一的分子化合物集成了太阳能电池从光收集，载流子生成和分离到传输和与外部电极接触所需的所有功能。描述了一种具有约60个步骤的会聚合成策略，涉及制备区域规则的低聚噻吩，卟啉锌，双吡啶吡啶（II）络合物，杂亚苯基亚乙烯基和功能性端基。基于目标分子上的光伏器件的初步调查，得到0.18 V，0.0044毫安厘米的值- 2，29％，对于开路电压（0.000081％V OC），短路电流（我SC），填充系数（FF）和效率（η）。这些差值进行比较，以与这给了0.7 V，0.046毫安厘米的值的低聚-3-己基噻吩得到的那些- 2，24.6％，而对于开路电压（0.0081％V OC），短路电流（我SC），填充系数（FF）和效率（η）。这后一种化合物也进行了研究与PCBM（1:1掺合物）的本体异质结装置，其得到0.43 V，0.45毫安厘米的值- 2，33
• Stepwise Unidirectional Synthesis of Oligo Phenylene Vinylenes with a Series of Monomers. Use in Plastic Solar Cells
  作者：Mikkel Jørgensen、Frederik C. Krebs

  DOI：10.1021/jo0506783

  日期：2005.7.1

  Four new monomers for directional stepwise synthesis of oligophenylenevinylenes (OPVs) (4-2[4-(5,5-dimethyl [1,31 dioxan-2-yl)-2,5-dipropoxyphenyl] vinyl }benzyl)phosphonic acid diethyl ester, (5-2- [4-(5,5-dimethyl [1,31 dioxan-2-yl)-2,5-dipropylphenyl] vinyl }thiophene-2-yl-methyl)phosphonic acid diethyl ester, (5-2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropoxyphenyl]vinyl}thiophene-2-yl-methyl)phosphonic acid diethyl ester, and (7-2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropylphenyl]-vinyl}benzo[1,2,5]thiadiazol-4-ylmethyl)phosphonic acid diethyl ester have been prepared. Trimeric OPVs were then synthesized and tested as active materials in photovoltaic cells. Conversion efficiencies in the range of 0.5-1% were obtained in blends with the soluble C-60 derivative PCBM. A terpyridine end-functionalized trimer and a heterotrimer with a mixed composition of monomers were also prepared.