tetrathiafulvalene-tetrathiolate | 64394-49-6

• 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: tetrathiafulvalene-tetrathiolate
• 英文别名: (tetrathiafulvalene-tetrathiolate)(4-)；2-(4,5-Disulfido-1,3-dithiol-2-ylidene)-1,3-dithiole-4,5-dithiolate；2-(4,5-disulfido-1,3-dithiol-2-ylidene)-1,3-dithiole-4,5-dithiolate
• CAS: 64394-49-6
• 化学式: C₆S₈
• 分子量: 328.594
• InChiKey: BXAHRSQOIGUFJO-UHFFFAOYSA-J

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tetrathiafulvalene-tetrathiolate 在 lithium aluminium tetrahydride 作用下， 生成 2-{2-[2-(5,4',5'-Tris-{2-[2-(2-mercapto-ethoxy)-ethoxy]-ethylsulfanyl}-[2,2']bi[[1,3]dithiolylidene]-4-ylsulfanyl)-ethoxy]-ethoxy}-ethanethiol
  参考文献：
  名称：

  Self-assembled monolayers with oligo-ethyleneoxy linkages on flat and curved gold surfaces

  摘要：

  The preparation and properties of the self-assembled monolayers with oligo-ethyleneoxy linkages on flat and curved gold surfaces have been described. The electrochemical properties of the self-assembled monolayers of a tetrathiafulvalenyl-alkane monothiol and the ether-substituted alkane monothiol adsorbed onto gold electrodes showed no difference in their redox potentials and surface coverages. In contrast, the difference between the alkyl chain and the oxy-alkyl chain in the redox potentials and surface coverages was found in the self-assembled monolayers of the tetrathiafulvalenyl-tetrathiol and the ether-substituted tetrathiol adsorbed onto gold electrodes. The reaction of a thiol bearing oligo-ethyleneoxy linkages with octanethiolate-stabilized gold clusters gave the new oxy-Au clusters containing ether linkages which were dissolved in nonpolar and polar solvents. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00396-x
• 作为产物：
  描述：

  2,3,6,7-四(2-氰乙基硫代)四硫富瓦烯 在 cesium hydroxide 作用下， 生成 tetrathiafulvalene-tetrathiolate
  参考文献：
  名称：

  Tetrathiafulvalene Thiolates: Important Synthetic Building Blocks for Macrocyclic and Supramolecular Chemistry

  摘要：

  现在，通过使用一整套基于四噻吩（TTF）的构建模块，可以制备相当复杂的分子组装体。2-Cyanoethyl 基团是 1,3-二硫代-2-硫酮-4,5-二硫环戊烯和 TTF-硫代酸酯的通用保护基团，对该基团进行简易脱保护已被证明是将 TTF 单元加入大环和超分子化合物的可行方法。特别是分步保护-保护方法已被我们小组广泛用于制备二维和三维大环（单环、双环和三环）以及基于 TTF 的超分子体系。我们通过几个实例来说明所生成的硫代化合物的生成、利用和应用范围：树枝状和低聚 TTF、三维四富戊烯烷、含 TTF 的卡替烷和轮烷以及以 TTF 为捐献部分的捐献受体系统。

  DOI：

  10.1055/s-1997-1001

文献信息

• [EN] SULFUR-CONTAINING INORGANIC-ORGANIC HYBRID MATERIALS AND METHODS FOR MAKING THE SAME<br/>[FR] MATÉRIAUX HYBRIDES INORGANIQUES-ORGANIQUES CONTENANT DU SOUFRE ET LEURS PROCÉDÉS DE FABRICATION
  申请人：UNIV CHICAGO

  公开号：WO2021081172A1

  公开（公告）日：2021-04-29

  Coordination complexes of tetrathiafulvalene-based dithiolene linkers, such as tetrathiafulvalene-2,3,6,7-tetrathiolate (TTFtt), and their oxidation products are described. The coordination complexes can include metals such as tin or silicon. Also described are methods of using the coordination complexes in transmetallation reactions, e.g., to prepare sulfur coordination polymers, and sulfur coordination polymers doped with tetrathiafulvalene-based dithiolene linkers having different oxidation states.

  描述了基于四硫富瓦烯二硫辛联结物的配位配合物，例如四硫富瓦烯-2,3,6,7-四硫酸盐（TTFtt）及其氧化产物。这些配位配合物可以包括金属，如锡或硅。还描述了利用这些配位配合物进行金属交换反应的方法，例如用于制备硫配位聚合物，以及掺杂有具有不同氧化态的基于四硫富瓦烯二硫辛联结物的硫配位聚合物。
• Gold Electrodes Modified with Multilayers of M–TTF–Tetrathiolate (M = Ni^IIand Cu^II, TTF = Tetrathiafulvalene)
  作者：Yu Liu、Qin-Yu Zhu、Guo-Qing Bian、Wen-Juan Guo、Wen Lu、Jie Dai

  DOI：10.1246/cl.2007.614

  日期：2007.5.5

  Gold electrodes, on which multilayered metal–TTF derivatives (M–TTFS4) were assembled, exhibit a redox activity, and the redox potentials are sensitive to the metal ions being coordinated. The M–TTFS4 showed broad and very strong absorbance in the range of near IR, attributed to the charge-transfer band between the metal ions and the ligand.

  组装了多层金属-TTF 衍生物（M-TTFS4）的金电极具有氧化还原活性，氧化还原电位对配位的金属离子很敏感。M-TTFS4 在近红外范围内显示出宽而强的吸光度，这归因于金属离子与配体之间的电荷转移带。
• Saito, Gunzi; Hayashi, Hitoshi; Enoki, Toshiaki, Molecular Crystals and Liquid Crystals (1969-1991), 1985, vol. 120, p. 341 - 344
  作者：Saito, Gunzi、Hayashi, Hitoshi、Enoki, Toshiaki、Inokuchi, Hiroo

  DOI：——

  日期：——
• Tetrathiafulvalene Thiolates: Important Synthetic Building Blocks for Macrocyclic and Supramolecular Chemistry
  作者：Klaus Simonsen、Jan Becher

  DOI：10.1055/s-1997-1001

  日期：1997.11

  The Preparation of rather complex molecular assemblies can now be accomplished by using a complete set of tetrathiafulvalene (TTF) based building blocks. The facile deprotection of the 2-cyanoethyl group, a versatile protecting group for 1,3-dithiolium-2-thione-4,5-dithiolaes and TTF-thiolates have proven to be a viable method for the incorporation of TTF units into macrocyclic and supramolecular compounds. Especially the stepwise protection-deprotection methodology have been used extensively by our group for the preparation of two and three dimensional macrocyclic (mono-, bis- and tricyclic) as well as TTF-based supramolecular systems. The generation, utilization and scope of the generated thiolates are illustrated by several examples: Dendrimeric and oligo-TTF's, three dimensional tetrathafulvalenophanes, TTF-containing catenanes and rotaxanes and donor acceptor systems based on TTF as the donating portion.

  现在，通过使用一整套基于四噻吩（TTF）的构建模块，可以制备相当复杂的分子组装体。2-Cyanoethyl 基团是 1,3-二硫代-2-硫酮-4,5-二硫环戊烯和 TTF-硫代酸酯的通用保护基团，对该基团进行简易脱保护已被证明是将 TTF 单元加入大环和超分子化合物的可行方法。特别是分步保护-保护方法已被我们小组广泛用于制备二维和三维大环（单环、双环和三环）以及基于 TTF 的超分子体系。我们通过几个实例来说明所生成的硫代化合物的生成、利用和应用范围：树枝状和低聚 TTF、三维四富戊烯烷、含 TTF 的卡替烷和轮烷以及以 TTF 为捐献部分的捐献受体系统。
• Self-assembled monolayers with oligo-ethyleneoxy linkages on flat and curved gold surfaces
  作者：Hidetaka Nakai、Hisashi Fujihara

  DOI：10.1016/s0022-328x(00)00396-x

  日期：2000.10

  The preparation and properties of the self-assembled monolayers with oligo-ethyleneoxy linkages on flat and curved gold surfaces have been described. The electrochemical properties of the self-assembled monolayers of a tetrathiafulvalenyl-alkane monothiol and the ether-substituted alkane monothiol adsorbed onto gold electrodes showed no difference in their redox potentials and surface coverages. In contrast, the difference between the alkyl chain and the oxy-alkyl chain in the redox potentials and surface coverages was found in the self-assembled monolayers of the tetrathiafulvalenyl-tetrathiol and the ether-substituted tetrathiol adsorbed onto gold electrodes. The reaction of a thiol bearing oligo-ethyleneoxy linkages with octanethiolate-stabilized gold clusters gave the new oxy-Au clusters containing ether linkages which were dissolved in nonpolar and polar solvents. (C) 2000 Elsevier Science S.A. All rights reserved.