(E,E)-5,5'-bis[2-(2-thienyl)-1-ethenyl]-2,2'-bithiophene | 38260-92-3

• 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: (E,E)-5,5'-bis[2-(2-thienyl)-1-ethenyl]-2,2'-bithiophene
• 英文别名: 2-[(E)-2-thiophen-2-ylethenyl]-5-[5-[(E)-2-thiophen-2-ylethenyl]thiophen-2-yl]thiophene
• CAS: 38260-92-3
• 化学式: C₂₀H₁₄S₄
• 分子量: 382.595
• InChiKey: OGDGPBORZJRNEK-KQQUZDAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  [2,2’]-双噻吩-5,5‘-二甲醛 、 2-(噻吩甲基)膦酸二乙酯 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以87%的产率得到(E,E)-5,5'-bis[2-(2-thienyl)-1-ethenyl]-2,2'-bithiophene
  参考文献：
  名称：

  Effect of Local Molecular Structure on the Chain-Length Dependence of the Electronic Properties of Thiophene-Based π-Conjugated Systems

  摘要：

  Three series of thiophene-based pi-conjugated oligomers built with different combinations of thiophene cycles and double bonds have been synthesized and characterized. The analysis of the chain length dependence of the electronic, electrochemical, and vibrational properties of the three series of oligomers has been carried out using cyclic voltammetry, UV-vis, IR, and Raman spectroscopies. These various investigations provide consistent results showing that incorporation of ethylenic linkages in an oligothiophene structure leads to a faster decrease of the HOMO-LUMO gap with chain extension due to the combined effects of enhanced planarity and lower overall aromatic character of the system. Although the incorporation of two consecutive double bonds in the system leads to a stabilization of the dicationic state, this structural modification does not produce the expected further decrease of the HOMO-LUMO gap at large chain extension. This phenomenon is discussed on the basis of an interplay between aromaticity and bond length alternation.

  DOI：

  10.1021/jo034319o

文献信息

• Effect of Local Molecular Structure on the Chain-Length Dependence of the Electronic Properties of Thiophene-Based π-Conjugated Systems
  作者：Pierre Frère、Jean-Manuel Raimundo、Philippe Blanchard、Jacques Delaunay、Pascal Richomme、Jean-Louis Sauvajol、Jesus Orduna、Javier Garin、Jean Roncali

  DOI：10.1021/jo034319o

  日期：2003.9.1

  Three series of thiophene-based pi-conjugated oligomers built with different combinations of thiophene cycles and double bonds have been synthesized and characterized. The analysis of the chain length dependence of the electronic, electrochemical, and vibrational properties of the three series of oligomers has been carried out using cyclic voltammetry, UV-vis, IR, and Raman spectroscopies. These various investigations provide consistent results showing that incorporation of ethylenic linkages in an oligothiophene structure leads to a faster decrease of the HOMO-LUMO gap with chain extension due to the combined effects of enhanced planarity and lower overall aromatic character of the system. Although the incorporation of two consecutive double bonds in the system leads to a stabilization of the dicationic state, this structural modification does not produce the expected further decrease of the HOMO-LUMO gap at large chain extension. This phenomenon is discussed on the basis of an interplay between aromaticity and bond length alternation.