5''-hydroxymethyl-5-(diphenyloxophosphino)-2,2':5',2''-terthiophene | 1271740-56-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5''-hydroxymethyl-5-(diphenyloxophosphino)-2,2':5',2''-terthiophene
• 英文别名: [5-[5-(5-Diphenylphosphorylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]methanol；[5-[5-(5-diphenylphosphorylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]methanol
• CAS: 1271740-56-7
• 化学式: C₂₅H₁₉O₂PS₃
• 分子量: 478.596
• InChiKey: URUUBRWRMLFROE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  94.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5''-hydroxymethyl-5-(diphenyloxophosphino)-2,2':5',2''-terthiophene 在 sodium hydroxide 、 silver(l) oxide 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.5h， 以58%的产率得到5-(diphenyloxophosphino)-2,2':5',2''-terthiophene-5''-carboxylic acid
  参考文献：
  名称：

  Syntheses, and Optical, Fluorescence, and Nonlinear Optical Characterization of Phosphine-Substituted Terthiophenes

  摘要：

  Earlier studies of phosphine-substituted terthiophenes have demonstrated that some of these materials exhibit nonlinear absorption at 532 nm. However, this wavelength is significantly removed from the linear absorption maxima of the complexes, suggesting that better nonlinear absorption might be observed at wavelengths closer to the linear absorption maxima. To investigate this possibility, a library of compounds has been prepared either by varying the group attached to the nonbonding pair of electrons on the phosphorus atoms of 5,5 ''-bis(diphenylphosphino)2,2':5',2 ''-terthiophene (PT3P), or by introducing additional substituents on the 5 ''-position of 5-(diphenylphosphino)2,2':5',2 ''-terthiophene (PT3). All these compounds have been characterized using multinuclear NMR, UV-vis, and fluorescence spectroscopy. The compounds are strongly fluorescent, and both the fluorescence wavelength and the intensity depend upon the thiophene substituents. The nonlinear optical properties have also been evaluated at various wavelengths in the blue region. Each compound exhibits reverse saturable absorption, and the intensity of the reverse saturable absorption at a particular wavelength depends on the chemical structure of the compound.

  DOI：

  10.1021/ic101624y
• 作为产物：
  描述：

  5-(diphenyloxophosphino)-2,2':5',2''-terthiophene-5''-carbaldehyde 在 sodium tetrahydroborate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以90%的产率得到5''-hydroxymethyl-5-(diphenyloxophosphino)-2,2':5',2''-terthiophene
  参考文献：
  名称：

  Syntheses, and Optical, Fluorescence, and Nonlinear Optical Characterization of Phosphine-Substituted Terthiophenes

  摘要：

  Earlier studies of phosphine-substituted terthiophenes have demonstrated that some of these materials exhibit nonlinear absorption at 532 nm. However, this wavelength is significantly removed from the linear absorption maxima of the complexes, suggesting that better nonlinear absorption might be observed at wavelengths closer to the linear absorption maxima. To investigate this possibility, a library of compounds has been prepared either by varying the group attached to the nonbonding pair of electrons on the phosphorus atoms of 5,5 ''-bis(diphenylphosphino)2,2':5',2 ''-terthiophene (PT3P), or by introducing additional substituents on the 5 ''-position of 5-(diphenylphosphino)2,2':5',2 ''-terthiophene (PT3). All these compounds have been characterized using multinuclear NMR, UV-vis, and fluorescence spectroscopy. The compounds are strongly fluorescent, and both the fluorescence wavelength and the intensity depend upon the thiophene substituents. The nonlinear optical properties have also been evaluated at various wavelengths in the blue region. Each compound exhibits reverse saturable absorption, and the intensity of the reverse saturable absorption at a particular wavelength depends on the chemical structure of the compound.

  DOI：

  10.1021/ic101624y