4',5'-dimethyl-EDO-TTF | 136040-36-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶英
• 英文名称: 4',5'-dimethyl-EDO-TTF
• 英文别名: DMEDO-TTF；2-(4,5-Dimethyl-1,3-dithiol-2-ylidene)-5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dioxine
• CAS: 136040-36-3
• 化学式: C₁₀H₁₀O₂S₄
• 分子量: 290.452
• InChiKey: NKQREBRDKYCLOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4',5'-dimethyl-EDO-TTF 在 tert-butylammonium hexafluorophosphate(V) 作用下， 以 氯苯 为溶剂， 生成
  参考文献：
  名称：

  Structural Transitions from Triangular to Square Molecular Arrangements in the Quasi-One-Dimensional Molecular Conductors (DMEDO-TTF)₂XF₆(X = P, As, and Sb)

  摘要：

  A series of quasi-one-dimensional molecular conductors (DMEDO-TTF)(2)XF6 (X = P, As, and Sb), where DMEDO-TTF is dimethyl(ethylenedioxy)tetrathiafulvalene, undergo characteristic structural transitions in the range of 130-195 K for the PF6 salt and 222-242 K for the AsF6 salt. The dramatic structural transition is induced by the order of the ethylenedioxy moiety, and the resulting anion rotation leads to the reconstruction of the H center dot center dot center dot F interaction between the methyl groups and the anions. The unique hydrogen bonds play a crucial role in the transition. As a result, the molecular packing is rearranged entirely; the high-temperature molecular stacks with an ordinary quasi-triangular molecular network transforms to a quasi-square-like network, which has never been observed among organic conductors. Nonetheless, the low-temperature phase exhibits a good metallic conductivity as well, so the transition is a metal-metal (MM) transition. The resistivity measured along the perpendicular direction to the conducting ac-plane (rho(perpendicular to)) and the calculation of the Fermi surface demonstrate that the high-temperature metal phase is a one-dimensional metal, whereas the low-temperature metal phase has considerable interchain interaction. In the SbF6 salt, a similar structural transition takes place around 370 K, so that the quasi-square-like lattice is realized even at room temperature. Despite the largely different MM transition temperatures, all these salts undergo metal-insulator (MI) transitions approximately at the same temperature of 50 K. The low-temperature insulator phase is nonmagnetic, and the reflectance spectra suggest the presence of charge disproportionation with small charge difference (0.14).

  DOI：

  10.1021/ja303435n
• 作为产物：
  描述：

  4,5-ethylenedioxy-tetrathiafulvalene 、 碘甲烷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.12h， 以43%的产率得到4,5-ethylenedioxy-4'-methyltetrathiafulvalene
  参考文献：
  名称：

  Formation of two-dimensional metals by weak intermolecular interactions based on the asymmetric EDO-TTF derivatives

  摘要：

  研究人员以中等产率合成了两种单取代的 EDO-TTF 衍生物：4,5-亚乙二氧基-4′-甲基-TTF（MeEDO-TTF，2）和 4,5-亚乙二氧基-4′-甲硫基-TTF（MeSEDO-TTF，3）。根据循环伏安法和紫外-可见光谱法，这两种供体的 π 电子系统与母体分子 EDO-TTF 的电子结构相似。尽管这两种供体的组成不同，但它们的自由基阳离子盐却表现出相似的光学光谱，在 3.3 × 103 cm-1 左右有一个低洼吸收带，这与它们在室温下的良好导电性是一致的。这些盐的传输特性从稳定金属、金属-绝缘体过渡体系到半导体不等。大多数自由基阳离子盐在室温左右表现出保利顺磁性。稳定金属盐 (MeEDO-TTF)2X (X = BF4, ClO4) 的晶体结构呈现出一种新颖的供体堆积模式，计算得到的带状结构呈现出二维特征，这与它们的传输特性相一致。

  DOI：

  10.1039/b717621j