(E)-3-[5-[(1E,3E)-4-[5-[(E)-3-oxoprop-1-enyl]thiophen-2-yl]buta-1,3-dienyl]thiophen-2-yl]prop-2-enal | 609369-41-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: (E)-3-[5-[(1E,3E)-4-[5-[(E)-3-oxoprop-1-enyl]thiophen-2-yl]buta-1,3-dienyl]thiophen-2-yl]prop-2-enal
• CAS: 609369-41-7
• 化学式: C₁₈H₁₄O₂S₂
• 分子量: 326.44
• InChiKey: FQKIKTDUSROZRW-VYUKIJHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(噻吩甲基)膦酸二乙酯 、 (E)-3-[5-[(1E,3E)-4-[5-[(E)-3-oxoprop-1-enyl]thiophen-2-yl]buta-1,3-dienyl]thiophen-2-yl]prop-2-enal 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以60%的产率得到(E,E,E,E,E,E)-1,4-bis[5-[1-(4-(2-thienyl))-1,3-butadienyl]-2-thienyl]buta-1,3-diene
  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
• 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 、 乙醚 、 正己烷 为溶剂， 反应 7.0h， 生成 (E)-3-[5-[(1E,3E)-4-[5-[(E)-3-oxoprop-1-enyl]thiophen-2-yl]buta-1,3-dienyl]thiophen-2-yl]prop-2-enal
  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