diethyl 2,2'-bithien-5-ylphosphonate | 214695-88-2

• 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: diethyl 2,2'-bithien-5-ylphosphonate
• 英文别名: 2-diethoxyphosphoryl-5-thiophen-2-ylthiophene
• CAS: 214695-88-2
• 化学式: C₁₂H₁₅O₃PS₂
• 分子量: 302.355
• InChiKey: KMZKXNJPBSZSGT-UHFFFAOYSA-N

物化性质

• 沸点：
  407.910±35.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.292±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  diethyl 2,2'-bithien-5-ylphosphonate 、 nonane-1,9-diyl bis(5'-(7-bromo-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-[2,2'-bithiophene]-5-carboxylate) 在 正丁基锂 、 二异丙胺 、 三甲基氯化锡 、 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 73.0h， 以57%的产率得到9-[5-[5-[5-[5-[5-[Diethoxy(oxido)phosphaniumyl]thiophen-2-yl]thiophen-2-yl]-2,3-dihydrothieno[3,4-b][1,4]dioxin-7-yl]thiophen-2-yl]thiophene-2-carbonyl]oxynonyl 5-[5-[5-[5-[5-[diethoxy(oxido)phosphaniumyl]thiophen-2-yl]thiophen-2-yl]-2,3-dihydrothieno[3,4-b][1,4]dioxin-7-yl]thiophen-2-yl]thiophene-2-carboxylate
  参考文献：
  名称：

  Synthesis of Bridged Oligothiophenes:  Toward a New Class of Thiophene-Based Electroactive Surfactants

  摘要：

  A series of bridged oligothiophenes have been synthesized. Their novel molecular architecture, comprising two oligothiophenes linked together by a bridge at one a-extremity and one binding group at the other a-extremity, is expected to improve their utility as electroactive surfactants for semiconducting nanoparticles or organic electronics.

  DOI：

  10.1021/ol034398q
• 作为产物：
  描述：

  2,2'-联二噻吩 、 氯磷酸二乙酯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以86%的产率得到diethyl 2,2'-bithien-5-ylphosphonate
  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