2,3-bis(hydroxymethyl)-6,7-(ethylenedithio) tetrathiafulvalene | 142059-41-4

• 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: 2,3-bis(hydroxymethyl)-6,7-(ethylenedithio) tetrathiafulvalene
• 英文别名: 2,3-Bis(hydroxymethyl)-6,7-ethylenedithio-tetrathiafulvalene；[2-(5,6-Dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylidene)-5-(hydroxymethyl)-1,3-dithiol-4-yl]methanol
• CAS: 142059-41-4
• 化学式: C₁₀H₁₀O₂S₆
• 分子量: 354.584
• InChiKey: KSGFCTZEBGDLGF-UHFFFAOYSA-N

物化性质

• 沸点：
  516.8±50.0 °C(Predicted)
• 密度：
  1.80±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  192
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3-bis(hydroxymethyl)-6,7-(ethylenedithio) tetrathiafulvalene 在 18-冠醚-6 、 三溴化磷 、 potassium iodide 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 生成 1,2-cyclohexenyl-(ethylenedisulfanyltetrathiafulvalene)-[60]fullerene
  参考文献：
  名称：

  四硫富瓦烯冠醚[60]富勒烯衍生物的合成及金属离子络合研究

  摘要：

  描述了含有电子供体四硫富瓦烯和金属络合冠醚的两种新型 [60] 富勒烯衍生物的合成，并通过固液萃取技术、循环伏安法和 1 H NMR 光谱研究了它们与碱金属阳离子的络合能力。

  DOI：

  10.1002/1099-0690(200004)2000:7<1157::aid-ejoc1157>3.0.co;2-z
• 作为产物：
  描述：

  4-formyl-5-(diethoxymethyl)-1,3-dithiole-2-thione 在 sodium tetrahydroborate 、 甲酸 、 dicobalt octacarbonyl 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 2,3-bis(hydroxymethyl)-6,7-(ethylenedithio) tetrathiafulvalene
  参考文献：
  名称：

  2-Mono or 2,3-Bis(hydroxymethyl)-6,7-ethylenedithio-tetrathiafulvalenes: New potential precursors of organic metals endowed with hydrogen bonds

  摘要：

  The syntheses of new pi-unsymmetrical donors of the TTF family having half moiety of bis(ethylenedithio)-TTF (BEDT-TTF) and half moiety of TTF substituted with one (or two) hydroxymethyl group(s) are described. Their good pi-donating ability is demonstrated by cyclic voltammetry.

  DOI：

  10.1016/s0040-4039(00)79057-5

文献信息

• Redox-active self-assembled monolayers as novel solid contacts for ion-selective electrodes
  作者：Monia Fibbioli、Olivier Enger、François Diederich、Ernö Pretsch、Krisanu Bandyopadhyay、Sheng-Gao Liu、Luis Echegoyen、Philippe Bühlmann

  DOI：10.1039/a909532b

  日期：——

  A new methodology to fabricate solid-contact ion-selective electrodes (SC-ISEs) using SAMs of a lipophilic redox-active compound to facilitate the charge transfer across the interface leads to improved potential stability and prevents redox or O2 interference of valinomycin-based SC-ISEs.

  一种新的方法论，通过使用亲脂性红氧化活性化合物的自组装单层(SAMs)来制造固体接触离子选择电极(SC-ISEs)，以促进界面上的电荷转移，从而提高了电位稳定性，并防止了基于伏拉霉素的SC-ISEs受到氧化还原或O2的干扰。
• Remarkably stable self-assembled monolayers of new crown-ether annelated tetrathiafulvalene derivatives and their cation recognition properties†
  作者：Haiying Liu、Shenggao Liu、Luis Echegoyen

  DOI：10.1039/a904249k

  日期：——

  Bis-thioctic ester derivatives of crown-ether annelated tetrathiafulvalenes (TTFs) form extremely stable self-assembled monolayers (SAMs) on gold electrodes and can recognize alkali metal ions by cyclic voltammetry.

  冠醚环化四硫杂戊烯（TTFs）的双硫代酯衍生物能在金电极上形成极其稳定的自组装单层（SAMs），并能通过循环伏安法识别碱金属离子。
• Solid-State Transformations of Zinc 1,4-Benzenedicarboxylates Mediated by Hydrogen-Bond-Forming Molecules
  作者：Mark Edgar、Robert Mitchell、Alexandra M. Z. Slawin、Philip Lightfoot、Paul A. Wright

  DOI：10.1002/1521-3765(20011203)7:23<5168::aid-chem5168>3.0.co;2-s

  日期：2001.12.3

  The zinc 1,4-benzenedicarboxylates [Zn3(bdc)3(H2O)3] . 4 DMF (1; bdc = 1,4-benzenedicarboxylate), [Zn(bdc)(H2O)] . DMF (2), and [Zn(bdc)] DMF (3) crystallise at room temperature from mixtures of toluene/ dimethylformamide (DMF) under concentrated, dilute and dry conditions, respectively. The structure of phase 1 (monoclinic: P2(1)/c, a 13.065(1), b = 9.661(1), c = 18.456(1) A, beta = 106.868(2) degrees) consists of layers containing stacks of three zinc cations linked by mono- and bidentate bdc groups. Structure 1 converts to the known phase 2 by an irreversible, reconstructive phase transformation, whereas 2 and 3 interconvert reversibly upon the loss or addition of water. Removal of all solvent molecules included during crystallisation gives poorly crystalline [Zn(bdc)] (4), which is readily converted to highly crystalline solids upon contact with hydrogen-bond-forming molecules such as water, DMF and small alcohols. The crystal structures of the mono- and dihydrates [Zn(bdc)(H2O)] (6) and [Zn(bdc)-(H2O)2] (7) have been determined ab initio from powder X-ray diffraction data (compound 6, monoclinic: C2/c, a = 17.979(1), b = 6.352(1), c = 7.257(1) A, beta=91.477(1) compound 7, monoclinic: C2/c, a = 14.992(1), b = 5.0303(2), c = 12.098(1) A, beta = 103.82(1) degrees). The methanol adduct [Zn3(bdc)3] . 6CH3OH (5) is the same as that prepared previously by direct crystallisation. Comparison of these adduct structures with those prepared directly reveal that they are formed by in situ recrystallisations. Subsequent removal of included molecules gives amorphous [Zn(bdc)], which can be recrystallised again when placed in contact with hydrogen-bond-forming molecules.
• Dithia-Crown-Annelated Tetrathiafulvalene Disulfides:  Synthesis, Electrochemistry, Self-Assembled Films, and Metal Ion Recognition
  作者：Sheng-Gao Liu、Haiying Liu、Krisanu Bandyopadhyay、Zhiqiang Gao、Luis Echegoyen

  DOI：10.1021/jo000115l

  日期：2000.6.1

  The synthesis and electrochemistry of a series of tetrathiafulvalene (TTF) and dithia-crown-TTF derivatives attached with one or two disulfide group(s) 7a-f are reported. The self-assembled monolayers (SAMs) of these TTF disulfides on gold were prepared and characterized by reflection-absorption infrared spectroscopy. The SAMs are extremely stable under a wide variety of conditions and over extended periods of time and show remarkable electrochemical stability upon repeated potential scans. SAMs of the crown-TTF disulfides 7c,d,f can recognize alkali metal ions, and the process can be monitored following the electrochemical potential shift of the surface-confined TTF group.
• Studies of the First S-Position Isomer of Bis(ethylenedithio)tetrathiafulvalene
  作者：Piétrick Hudhomme、Philippe Blanchard、Marc Sallé、Soazig Le Moustarder、Amédée Riou、Michel Jubault、Alain Gorgues、Guy Duguay

  DOI：10.1002/anie.199708781

  日期：1997.5.2