3'-fluoro-4'-hexyl-2,2':5',2''-terthiophene | 1421780-74-6

• 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: 3'-fluoro-4'-hexyl-2,2':5',2''-terthiophene
• 英文别名: 3-Fluoro-4-hexyl-2,5-dithiophen-2-ylthiophene；3-fluoro-4-hexyl-2,5-dithiophen-2-ylthiophene
• CAS: 1421780-74-6
• 化学式: C₁₈H₁₉FS₃
• 分子量: 350.545
• InChiKey: PLHHVWOELIXGQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-己基噻吩 在 四(三苯基膦)钯 、 正丁基锂 、 四丁基氟化铵 、 溴 、 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 环己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 3'-fluoro-4'-hexyl-2,2':5',2''-terthiophene
  参考文献：
  名称：

  3-Fluoro-4-hexylthiophene as a Building Block for Tuning the Electronic Properties of Conjugated Polythiophenes

  摘要：

  3-Fluoro-4-hexylthiophene has been prepared by a synthetic route involving perbromination of 3-hexylthiophene followed by protection of the 2- and 5-positions of thiophene by trimethylsilyl groups and bromine/fluorine exchange. As expected, 3-hexyl-4-fluorothiophene oxidizes at a higher potential than 3-hexylthiophene; however, all attempts to electropolymerize this new thiophenic monomer have remained unsuccessful. Three terthienyls containing 3-hexylthiophene, 3-fluoro-4-hexylthiophene, and 3-bromo-4-hexylthiophene as the median group have been synthesized and used as substrates for electropolymerization. The electronic properties of the starting terthienyls and the resulting polymers have been analyzed by cyclic voltammetry and UV-vis spectroscopy, and the effects of substitution of the median thiophene ring are discussed.

  DOI：

  10.1021/jo302571u

文献信息

• 3-Fluoro-4-hexylthiophene as a Building Block for Tuning the Electronic Properties of Conjugated Polythiophenes
  作者：Frédéric Gohier、Pierre Frère、Jean Roncali

  DOI：10.1021/jo302571u

  日期：2013.2.15

  3-Fluoro-4-hexylthiophene has been prepared by a synthetic route involving perbromination of 3-hexylthiophene followed by protection of the 2- and 5-positions of thiophene by trimethylsilyl groups and bromine/fluorine exchange. As expected, 3-hexyl-4-fluorothiophene oxidizes at a higher potential than 3-hexylthiophene; however, all attempts to electropolymerize this new thiophenic monomer have remained unsuccessful. Three terthienyls containing 3-hexylthiophene, 3-fluoro-4-hexylthiophene, and 3-bromo-4-hexylthiophene as the median group have been synthesized and used as substrates for electropolymerization. The electronic properties of the starting terthienyls and the resulting polymers have been analyzed by cyclic voltammetry and UV-vis spectroscopy, and the effects of substitution of the median thiophene ring are discussed.