4,5-bis(dodecylthio)tetrathiafulvalene | 208449-59-6

• 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-bis(dodecylthio)tetrathiafulvalene
• 英文别名: 2-(1,3-Dithiol-2-ylidene)-4,5-bis(dodecylsulfanyl)-1,3-dithiole
• CAS: 208449-59-6
• 化学式: C₃₀H₅₂S₆
• 分子量: 605.139
• InChiKey: GZQBPKYXPWSMNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.1
• 重原子数：
  36
• 可旋转键数：
  24
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,5-bis(dodecylthio)tetrathiafulvalene 在 正丁基锂 、 全氟己基碘烷 作用下， 以 四氢呋喃 为溶剂， 以72%的产率得到4,5-Bis(dodecylsulfanyl)-2-(4-iodo-1,3-dithiol-2-ylidene)-1,3-dithiole
  参考文献：
  名称：

  Synthesis and Electrochromic Properties of Bis(2-tetrathiafulvalenylethynylphenyl)ethynes

  摘要：

  Bis(2-tetrathiafulvalenylethynylphenyl)ethynes 1a and 1b have been synthesized by the Sonogashira coupling reaction of 4-iodotetrathiafulvalenes with bis(2-ethynylphenyl)ethyne. The dimeric TTFs 1a and 1b form an open-chain anti conformation in the neutral and tetracation states, whereas la and 1b form a helical syn conformation in the mono- and dication states owing to their face-to-face interaction between the two TTF units. Such conformational changes lead to unique electrochromic and on-off switching properties of 1a and 1b in UV-vis-NIR spectra.

  DOI：

  10.3987/com-08-s(f)106
• 作为产物：
  描述：

  4,5-bis(dodecylthio)-1,3-dithiole-2-thione 在 lithium bromide 作用下， 以 六甲基磷酰三胺 为溶剂， 生成 4,5-bis(dodecylthio)tetrathiafulvalene
  参考文献：
  名称：

  方便的一步合成甲酰四硫富瓦烯乙烯基胶：新型NLO材料的构建基块

  摘要：

  描述了一种合成甲酰基四硫富瓦烯乙烯基酯的新方法，其中将四硫富瓦烯（TTF）或TTF的取代衍生物与二异丙基氨基化锂金属化，然后与一乙烯基酰胺反应，以一锅法生产相应的短多烯。

  DOI：

  10.1016/s0040-4039(98)00467-5

文献信息

• Self-assembly of tetrathiafulvalene derivatives at a liquid/solid interface—compositional and constitutional influence on supramolecular ordering
  作者：Mohamed M. S. Abdel-Mottaleb、Elba Gomar-Nadal、Mathieu Surin、Hiroshi Uji-i、Wael Mamdouh、Jaume Veciana、Vincent Lemaur、Concepció Rovira、Jérôme Cornil、Roberto Lazzaroni、David B. Amabilino、Steven De Feyter、Frans C. De Schryver

  DOI：10.1039/b509336h

  日期：——

  The self-assembly of a series of tetrathiafulvalene (TTF) derivatives at the interface between non-volatile organic solutions and the graphite surface has been studied by scanning tunnelling microscopy (STM). The TTFs have been prepared such that they bear none, one, two (in different constitutions) or four alkyl chains of different lengths and different functional groups. The STM images reveal that the packing of the TTF cores can effectively be controlled by changing the substitution pattern on the heterocycle. Several structures are seen at the interphase—parquet-type packing, single and double core tapes, and even isolated molecules—all of which have the TTF core essentially coplanar with the surface. Molecular modelling has shown that several orientations of the molecules are practically equal in energy on the graphite, which explains the polymorphous packing of some of the molecules. Solvent effects also play a role in determining the 2D structures.

  通过扫描隧道显微镜（STM）研究了非挥发性有机溶液与石墨表面之间的界面上的一系列四硫富瓦烯（TTF）衍生物的自组装。制备的TTF具有无、一、二（不同结构）或四个不同长度和不同官能团的烷基链。STM图像显示，通过改变杂环上的取代模式，可以有效地控制TTF核心的堆积。在界面上可以看到几种结构——镶木地板式堆积、单核和双核带，甚至还有孤立的分子——所有这些TTF核心都与表面基本共面。分子模型显示，在石墨上，分子的几种取向实际上具有相同的能量，这解释了某些分子的多晶型堆积。溶剂效应在决定二维结构方面也起着一定的作用。
• New planar and soluble tris-tetrathiafulvalene derivatives with threefold-symmetry
  作者：Alfonso González、José L Segura、Nazario Martı́n

  DOI：10.1016/s0040-4039(00)00344-0

  日期：2000.4

  Novel trimeric tetrathiafulvalene (TTF) derivatives with threefold-symmetry are built on the 1,3,5-benzene core. Long alkyl chains have been incorporated on the peripheral positions of the TTF moieties in order to increase the solubility of the final products. Electrochemical and spectroscopic studies of the target compounds suggest that there are no significant interactions between the TTF units because of their meta orientation. Semiempirical theoretical calculations indicate that the new systems exhibit a high structural anisotropy resembling that exhibited by discotic liquid crystals. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of bitetrathiafulvalenes with FeCl3-mediated homo-coupling of tetrathiafulvalenylmagnesium bromide and formation of nanostructures from bitetrathiafulvalenes having long alkylthio chains
  作者：Yohei Honna、Eigo Isomura、Hideo Enozawa、Masashi Hasegawa、Masayoshi Takase、Tohru Nishinaga、Masahiko Iyoda

  DOI：10.1016/j.tetlet.2009.11.106

  日期：2010.1

  The FeCl3-mediated homo-coupling of 4,5-bis(alkylthio)-4'-tetrathiafulvalenylmagnesium bromide 5 produced the corresponding bitetrathiafulvalene derivatives 2a-d in moderate yields (25-51%). Bitetrathiafulvalenes 2c and 2d having long alkylthio chains formed nanostructures and showed bulk electric conductivities (sigma(rt) = 2.6 - 8.0 x 10(-5) S cm(-1)) in the neutral state owing to the fastener effect. Interestingly, the nanofiber of tetrakis(dodecylthio)bitetrathiafulvalene 2d exhibited a p-type semiconductivity as detected by AFM. (C) 2009 Elsevier Ltd. All rights reserved.