4,4',6,6'-tetrahydro-Δ^2,2'-bithieno<3,4-d>-1,3-dithiole radical cation | 127501-69-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢噻吩类
• 英文名称: 4,4',6,6'-tetrahydro-Δ^2,2'-bithieno<3,4-d>-1,3-dithiole radical cation
• 英文别名: 4,4',6,6'-tetrahydro-Δ^2,2'-bithieno[3,4-d]-1,3-dithiole radical cation；2-(4,6-Dihydrothieno[3,4-d][1,3]dithiol-2-ylidene)-4,6-dihydrothieno[3,4-d][1,3]dithiole
• CAS: 127501-69-3
• 化学式: C₁₀H₈S₆
• 分子量: 320.57
• InChiKey: CPSLCFHLPIKKNH-UHFFFAOYSA-N

物化性质

• 熔点：
  222-223 °C
• 沸点：
  523.0±50.0 °C(predicted)
• 密度：
  1.75±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  4,4',6,6'-tetrahydro-Δ^2,2'-bithieno<3,4-d>-1,3-dithiole radical cation 生成 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile;2-(4,6-dihydrothieno[3,4-d][1,3]dithiol-2-ylidene)-4,6-dihydrothieno[3,4-d][1,3]dithiole
  参考文献：
  名称：

  Rovira Concepcio, Veciana Jaume, Santalo Nuria, Tarres Judit, Cirujeda Jo+, J. Org. Chem, 59 (1994) N 12, S 3307- 3313

  摘要：

  DOI：
• 作为产物：
  描述：

  4,6-dihydrothieno[3,4-d]-1,3-dithiol-2-thione 在 三甲氧基磷 作用下， 反应 1.0h， 以40%的产率得到4,4',6,6'-tetrahydro-Δ^2,2'-bithieno<3,4-d>-1,3-dithiole radical cation
  参考文献：
  名称：

  双（硫代二亚甲基）-四硫富瓦烯（BTDM-TTF）。具有相关氧化性能的新型π电子供体

  摘要：

  报道了新的硫代烷基取代的四硫富瓦烯双（硫代二亚甲基）四硫富瓦烯的合成和一些物理性质。BTDM-TTF的氧化电位表明分子内库仑排斥能低。

  DOI：

  10.1016/s0040-4039(01)93950-4

文献信息

• Bis(thiodimethylene)-tetrahiafulvalene (BTDM-TTF). A new π-electron donor with relevant oxidation properties
  作者：C. Rovira、N. Santalō、J. Veciana

  DOI：10.1016/s0040-4039(01)93950-4

  日期：1989.1

  The synthesis and some physical properties of a new thioalkyl substituted tetrathiafulvalene, bis(thiodimethylene)tetrathiafulvalene, are reported. Oxidation potentials of BTDM-TTF indicate a low intramolecular Coulomb repulsion energy.

  报道了新的硫代烷基取代的四硫富瓦烯双（硫代二亚甲基）四硫富瓦烯的合成和一些物理性质。BTDM-TTF的氧化电位表明分子内库仑排斥能低。
• ROVIRA, C.;SANTALO, N.;VECIANA, J., TETRAHEDRON LETT., 30,(1989) N1, C. 7249-7252
  作者：ROVIRA, C.、SANTALO, N.、VECIANA, J.

  DOI：——

  日期：——
• Rovira Concepcio, Veciana Jaume, Santalo Nuria, Tarres Judit, Cirujeda Jo+, J. Org. Chem, 59 (1994) N 12, S 3307- 3313
  作者：Rovira Concepcio, Veciana Jaume, Santalo Nuria, Tarres Judit, Cirujeda Jo+

  DOI：——

  日期：——
• Synthesis of Several Isomeric Tetrathiafulvalene .pi.-Electron Donors with Peripheral Sulfur Atoms. A Study of Their Radical Cations
  作者：Concepcio Rovira、Jaume Veciana、Nuria Santalo、Judit Tarres、Joan Cirujeda、Elies Molins、Jordi Llorca、Enrique Espinosa

  DOI：10.1021/jo00091a017

  日期：1994.6

  An efficient synthesis of one new (10) and three previously reported (9, 11, and 12) pi-electron donors, which have one sulfur atom in each of the outer five-membered rings attached to the TTF system, is presented. The radical cations derived from 9-11 have been studied by ESR spectroscopy and the spin density distribution of these radical cations, as well as those of other related radical cations, have been determined by MO calculations and correlated with the ESR spectral data. The single-crystal X-ray structures of pi-donors 9 and 12 are reported. The most remarkable fact of these structures is the transverse intermolecular contacts between interstacked molecules. The external sulfur atoms of 9 play a central role in its transverse structural pattern. Complexes of donors 9 and 10 with tetracyano-p-quinodimethane (TCNQ) and tetrafluorotetracyano-p-quinodimethane (TC-NQF(4)) have been obtained and characterized.