5'-(2,2'-bipyridin-4-yl)-2,2'-bithien-5-ylphosphonic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5'-(2,2'-bipyridin-4-yl)-2,2'-bithien-5-ylphosphonic acid
• 英文别名: [5-[5-(2-Pyridin-2-ylpyridin-4-yl)thiophen-2-yl]thiophen-2-yl]phosphonic acid
• 化学式: C₁₈H₁₃N₂O₃PS₂
• 分子量: 400.419
• InChiKey: PLDQXSIKNBOYRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  140
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,2′-二吡啶基 N-氧化物 在 四(三苯基膦)钯 乙酰溴 、 三甲基溴硅烷 、 硫酸 、 硝酸 、 三溴化磷 作用下， 以 甲苯 为溶剂， 反应 79.0h， 生成 5'-(2,2'-bipyridin-4-yl)-2,2'-bithien-5-ylphosphonic acid
  参考文献：
  名称：

  Synthesis and Optical Properties of Bifunctional Thiophene Molecules Coordinated to Ruthenium

  摘要：

  A series of unsymmetrical bi- and tetrathiophenes have been synthesized with bipyridine and phosphonic acid functional groups. To do this, phosphonic esters were bonded to thiophenes and the thiophenes coupled to bipyridine. After synthesis of the thienylbipyridines, bis(bipyridine) ruthenium was coordinated to them through the bipyridines. The thienylbipyridines absorb visible light and fluoresce; however, on attachment to ruthenium, both their fluorescence and that of ruthenium are quenched. An additional effect of coordinating ruthenium to the thiophenes is a new absorption band around 470 nm. Variation in oligothiophene length and bipyridine substitution position allowed comparison of the effect of these variables on electronic properties. The longer oligothiophenes display lower-energy absorptions and emissions than that of the shorter thiophenes. In contrast, the position of the bipyridine attachment does not have a large effect on the absorbance or emission wavelength, or on the fluorescence quantum yield.

  DOI：

  10.1021/jo070377o

文献信息

• Synthesis and Optical Properties of Bifunctional Thiophene Molecules Coordinated to Ruthenium
  作者：Joseph S. Bair、Roger G. Harrison

  DOI：10.1021/jo070377o

  日期：2007.8.31

  A series of unsymmetrical bi- and tetrathiophenes have been synthesized with bipyridine and phosphonic acid functional groups. To do this, phosphonic esters were bonded to thiophenes and the thiophenes coupled to bipyridine. After synthesis of the thienylbipyridines, bis(bipyridine) ruthenium was coordinated to them through the bipyridines. The thienylbipyridines absorb visible light and fluoresce; however, on attachment to ruthenium, both their fluorescence and that of ruthenium are quenched. An additional effect of coordinating ruthenium to the thiophenes is a new absorption band around 470 nm. Variation in oligothiophene length and bipyridine substitution position allowed comparison of the effect of these variables on electronic properties. The longer oligothiophenes display lower-energy absorptions and emissions than that of the shorter thiophenes. In contrast, the position of the bipyridine attachment does not have a large effect on the absorbance or emission wavelength, or on the fluorescence quantum yield.