4,5-dihexyl-4'-iodotetrathiafulvalene | 1092717-91-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫醇
• 英文名称: 4,5-dihexyl-4'-iodotetrathiafulvalene
• 英文别名: 4,5-dihexyl-4'-iodo-TTF；4,5-Dihexyl-2-(4-iodo-1,3-dithiol-2-ylidene)-1,3-dithiole
• CAS: 1092717-91-3
• 化学式: C₁₈H₂₇IS₄
• 分子量: 498.581
• InChiKey: ZIFBWPNNHNRFCA-UHFFFAOYSA-N

物化性质

• 沸点：
  452.5±45.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  丙醛二乙基乙缩醛 、 4,5-dihexyl-4'-iodotetrathiafulvalene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 反应 3.0h， 以77%的产率得到4-(3,3-diethoxyprop-1-ynyl)-4',5'-dihexyltetrathiafulvalene
  参考文献：
  名称：

  Acetylenic tetrathiafulvalene-dicyanovinyl donor-acceptor chromophores

  摘要：

  通过高度不稳定的 TTF 连接丙炔醛或酮衍生物的 Knoevenagel 缩合反应，制备出了包含四噻富戊二烯（TTF）供体单元和一个或两个氰基乙炔勒烯（CEE）受体单元的化合物。由此制备的 TTF-CEE 是一种非常强的发色团，具有超过 900 纳米的低能末端吸收。这些分子经历了 TTF 单元的可逆氧化，并通过光谱电化学阐明了氧化物的光学特性。

  DOI：

  10.1039/b909886k
• 作为产物：
  描述：

  4,5-dihexyltetrathiafulvalene 在 lithium diisopropyl amide 、 1,2-二碘乙烷 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以78%的产率得到4,5-dihexyl-4'-iodotetrathiafulvalene
  参考文献：
  名称：

  Synthesis and Characterization of Tetrathiafulvalene-Substituted Di- and Tetraethynylethenes with p-Nitrophenyl Acceptors

  摘要：

  Novel di- and tetraethynylethene (DEE and TEE) compounds functionalized with tetrathiafulvalene (TTF) donor groups and p-nitrophenyl acceptor groups were synthesized by palladium-catalyzed cross-coupling reactions under various conditions. The molecules are strong chromophores and were investigated for their optical properties. Placement of two TTFs and two p-nitrophenyls about a central TEE core provides a molecule with a high third-order optical nonlinearity. The molecules experience reversible oxidations of the TTF units, and the optical properties of the oxidized species were elucidated by spectroelectrochemistry. The degree of quinoid character of the p-nitrophenyl in the molecules was determined by X-ray crystallography.

  DOI：

  10.1021/jo802190q

文献信息

• Synthesis and Characterization of Tetrathiafulvalene-Substituted Di- and Tetraethynylethenes with <i>p</i>-Nitrophenyl Acceptors
  作者：Asbjørn S. Andersson、Lasse Kerndrup、Anders Ø. Madsen、Kristine Kilså、Mogens Brøndsted Nielsen、Philip R. La Porta、Ivan Biaggio

  DOI：10.1021/jo802190q

  日期：2009.1.2

  Novel di- and tetraethynylethene (DEE and TEE) compounds functionalized with tetrathiafulvalene (TTF) donor groups and p-nitrophenyl acceptor groups were synthesized by palladium-catalyzed cross-coupling reactions under various conditions. The molecules are strong chromophores and were investigated for their optical properties. Placement of two TTFs and two p-nitrophenyls about a central TEE core provides a molecule with a high third-order optical nonlinearity. The molecules experience reversible oxidations of the TTF units, and the optical properties of the oxidized species were elucidated by spectroelectrochemistry. The degree of quinoid character of the p-nitrophenyl in the molecules was determined by X-ray crystallography.
• Acetylenic tetrathiafulvalene-dicyanovinyl donor-acceptor chromophores
  作者：Asbjørn Sune Andersson、François Diederich、Mogens Brøndsted Nielsen

  DOI：10.1039/b909886k

  日期：——

  Compounds incorporating the tetrathiafulvalene (TTF) donor unit and one or two cyanoethynylethene (CEE) acceptor units were prepared by Knoevenagel condensations of highly unstable, TTF-linked propargylic aldehyde or ketone derivatives. The resulting TTF-CEEs are very strong chromophores with low-energy end-absorptions beyond 900 nm. The molecules experience reversible oxidations of the TTF unit, and the optical properties of the oxidised species were elucidated by spectroelectrochemistry.

  通过高度不稳定的 TTF 连接丙炔醛或酮衍生物的 Knoevenagel 缩合反应，制备出了包含四噻富戊二烯（TTF）供体单元和一个或两个氰基乙炔勒烯（CEE）受体单元的化合物。由此制备的 TTF-CEE 是一种非常强的发色团，具有超过 900 纳米的低能末端吸收。这些分子经历了 TTF 单元的可逆氧化，并通过光谱电化学阐明了氧化物的光学特性。