4,5-bis(dodecylthio)-4',5'-bis(methoxycarbonyl)-tetrathiafulvalene | 321140-51-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4,5-bis(dodecylthio)-4',5'-bis(methoxycarbonyl)-tetrathiafulvalene
• 英文别名: 4,5-bis(dodecylthio)-4',5'-bis(methoxycarbonyl)tetrathiafulvalene；2,3-bis(dodecylthio)-6,7-bis(methoxycarbonyl)tetrathiafulvalene；Dimethyl 2-[4,5-bis(dodecylsulfanyl)-1,3-dithiol-2-ylidene]-1,3-dithiole-4,5-dicarboxylate；dimethyl 2-[4,5-bis(dodecylsulfanyl)-1,3-dithiol-2-ylidene]-1,3-dithiole-4,5-dicarboxylate
• CAS: 321140-51-6
• 化学式: C₃₄H₅₆O₄S₆
• 分子量: 721.212
• InChiKey: NRNHNHQMOHBVRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.3
• 重原子数：
  44
• 可旋转键数：
  28
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  204
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4,5-bis(dodecylthio)-4',5'-bis(methoxycarbonyl)-tetrathiafulvalene 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到[2-[4,5-Bis(dodecylsulfanyl)-1,3-dithiol-2-ylidene]-5-(hydroxymethyl)-1,3-dithiol-4-yl]methanol
  参考文献：
  名称：

  A New Photoactive and Highly Soluble C₆₀−TTF−C₆₀ Dimer:  Charge Separation and Recombination

  摘要：

  The covalent linkage of two [60]fullerene cores to a tetrathiafulvalene (TTF) donor affords a soluble and photoactive C-60-TTF-C-60 triad, Spectroscopic and photophysical characterization of the C-60-TTF-C-60 triad are given. Although the cyclic voltammetry measurements reveal no notable interaction between the chromophores in the ground state, photophysical data show that in the excited state an intramolecular electron transfer, evolving from the TTF donor to the singlet state of C-60, prevails, yielding a long-lived charge separated radical pair.

  DOI：

  10.1021/ol006645l
• 作为产物：
  描述：

  4,5-bis(methoxycarbonyl)-1,3-dithiole-2-one 、 4,5-bis(dodecylthio)-1,3-dithiole-2-thione 以 various solvent(s) 为溶剂， 反应 4.0h， 以57%的产率得到4,5-bis(dodecylthio)-4',5'-bis(methoxycarbonyl)-tetrathiafulvalene
  参考文献：
  名称：

  基于简单 4,5-双（十二烷基硫基）-和 4,5-双（十八烷基硫基）-4',5'-双（甲氧基羰基）四硫富瓦烯的电活性纳米线

  摘要：

  4,5-双（十二烷基硫基）-和 4,5-双（十八烷基硫基）-4',5'-双（甲氧基羰基）四硫富瓦烯（1a 和 1b）对己烷、环己烷、十氢化萘和乙醚具有胶凝能力电...

  DOI：

  10.1246/cl.2007.720

文献信息

• A convenient one-step synthesis of formyltetrathiafulvalene vinylogs: Building blocks for new NLO materials
  作者：Mar González、Nazario Matín、JoséL. Segura、Javier Garín、Jesús Orduna

  DOI：10.1016/s0040-4039(98)00467-5

  日期：1998.5

  A new method for the synthesis of formyltetrathiafulvalene vinylogs in which tetrathiafulvalene (TTF) or a substituted derivative of TTF is metalated with lithium diisopropylamide and then reacted with a vinylogous amide to yield the corresponding short polyenals in a one-pot process is described.

  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。
• 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。
• Pyridazine-3,6-diol-annulated Tetrathiafulvalene: Self-assembly and Fiber Formation Triggered by Diamine Addition
  作者：Ryota Inoue、Masashi Hasegawa、Yasuhiro Mazaki

  DOI：10.1246/cl.141165

  日期：2015.4.5

  Self-assembly and fibrous structure formation based on pyridazine-3,6-diol-annulated tetrathiafulvalene derivative were investigated. Although the molecules formed a trimeric assembly with complementary hydrogen bonds in solution, the addition of water produced micrometer fibrous structures. On the other hand, mixing of diamines (NH2–R–NH2) promoted reorganization of the self-assembly, and various nanoobjects were formed.

  研究了基于哒嗪-3,6-二醇annulated四硫代富勒烯衍生物的自组装和纤维结构形成。虽然分子在溶液中形成了具有互补氢键的三聚体组装，但加入水后会产生微米级的纤维结构。另一方面，二胺（NH2-R-NH2）的混合促进了自组装的重组，并形成了各种纳米物体。
• Self-assembly and Solvatochromic Fiber Formation of 4,5-Bis(dodecylthio)tetrathiafulvalene-4′-carboxylic Acid and Its Derivatives
  作者：Hideo Enozawa、Youhei Honna、Masahiko Iyoda

  DOI：10.1246/cl.2007.1434

  日期：2007.12.5

  TTF-carboxylic acid 2 exhibits gelling ability for hexane and cyclohexane to form an orange fibrous material and shows solvatochromism both in solution and in the fiber formation to produce a reddish-purple fibrous material from acetonitrile. Moreover, the corresponding ester 1 forms yellow fibers from acetonitrile. However, the tetrabutylammonium salt 3 produces fine microcrystals without gel or fiber formation.

  TTF-羧酸2对己烷和环己烷具有胶凝能力，形成橙色纤维状物质，并且在溶液和纤维形成过程中均表现出溶剂色变，从乙腈中生成红紫色纤维状物质。此外，相应的酯1从乙腈中形成黄色纤维。然而，四丁基铵盐3产生细小的微晶，不形成凝胶或纤维。
• Electroactive Nanowires Based on Simple 4,5-Bis(dodecylthio)- and 4,5-Bis(octadecylthio)-4′,5′-bis(methoxycarbonyl)tetrathiafulvalenes
  作者：Yusuke Kobayashi、Masashi Hasegawa、Hideo Enozawa、Masahiko Iyoda

  DOI：10.1246/cl.2007.720

  日期：2007.6.5

  4,5-Bis(dodecylthio)- and 4,5-bis(octadecylthio)-4′,5′-bis(methoxycarbonyl)tetrathiafulvalenes (1a and 1b) exhibit gelling ability for hexane, cyclohexane, decalin, and diethyl ether to form electr...

  4,5-双（十二烷基硫基）-和 4,5-双（十八烷基硫基）-4',5'-双（甲氧基羰基）四硫富瓦烯（1a 和 1b）对己烷、环己烷、十氢化萘和乙醚具有胶凝能力电...