S-(2,3-dihydrothieno[3,4-b][1,4]oxathiin-3-yl)-methyl 4,4,5,5,5-pentafluoropentanethioate | 1333236-78-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: S-(2,3-dihydrothieno[3,4-b][1,4]oxathiin-3-yl)-methyl 4,4,5,5,5-pentafluoropentanethioate
• 英文别名: S-(2,3-dihydrothieno[3,4-b][1,4]oxathiin-3-ylmethyl) 4,4,5,5,5-pentafluoropentanethioate
• CAS: 1333236-78-4
• 化学式: C₁₂H₁₁F₅O₂S₃
• 分子量: 378.408
• InChiKey: DWKQXSRUDGVLJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  (2,3-dihydrothieno[3,4-b][1,4]oxathiin-3-yl)methanethiol 、 4,4,5,5,5-五氟戊酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 以25%的产率得到S-(2,3-dihydrothieno[3,4-b][1,4]oxathiin-3-yl)-methyl 4,4,5,5,5-pentafluoropentanethioate
  参考文献：
  名称：

  Superhydrophobic Fiber Mats by Electrodeposition of Fluorinated Poly(3,4-ethyleneoxythiathiophene)

  摘要：

  The control of surface morphology and wettability is crucial in the development of superhydrophobic surfaces, which implies new strategy and molecular design. In this Article, we report the synthesis, characterization, and electrochemical properties of original 3,4-ethyleneoxythiathiophenes (EOTT) as platform molecules and its derivatives bearing a semifluorinated chain of various length (F-octyl, F-hexyl, F-butyl, and F-ethyl). We report the influence of the fluorinated chain length as well as the presence of sulfur atoms in the monomer on the surface construction and nonwetting properties of the corresponding electrodeposited polymer films. Surprisingly, these films exhibit the possibility to obtain extremely long polymer fibers with a possible control of their length by a careful choice in the monomer structure. We show that the presence of sulfur atoms in the monomer structure seems to be necessary to modulate the formation of extremely long polymer fibers by aggregation of smaller polymer fibrils. In this Article, the formation of superhydrophobic material (contact angle above 150 degrees) for four, six, and eight fluoromethylene units but also highly hydrophobic surfaces (contact angle above 125 degrees) from extremely short chains (two fluoromethylene units) is also demonstrated.

  DOI：

  10.1021/ja205283b

文献信息

• Superhydrophobic Fiber Mats by Electrodeposition of Fluorinated Poly(3,4-ethyleneoxythiathiophene)
  作者：Thierry Darmanin、Frédéric Guittard

  DOI：10.1021/ja205283b

  日期：2011.10.5

  The control of surface morphology and wettability is crucial in the development of superhydrophobic surfaces, which implies new strategy and molecular design. In this Article, we report the synthesis, characterization, and electrochemical properties of original 3,4-ethyleneoxythiathiophenes (EOTT) as platform molecules and its derivatives bearing a semifluorinated chain of various length (F-octyl, F-hexyl, F-butyl, and F-ethyl). We report the influence of the fluorinated chain length as well as the presence of sulfur atoms in the monomer on the surface construction and nonwetting properties of the corresponding electrodeposited polymer films. Surprisingly, these films exhibit the possibility to obtain extremely long polymer fibers with a possible control of their length by a careful choice in the monomer structure. We show that the presence of sulfur atoms in the monomer structure seems to be necessary to modulate the formation of extremely long polymer fibers by aggregation of smaller polymer fibrils. In this Article, the formation of superhydrophobic material (contact angle above 150 degrees) for four, six, and eight fluoromethylene units but also highly hydrophobic surfaces (contact angle above 125 degrees) from extremely short chains (two fluoromethylene units) is also demonstrated.