2,5-bis(1,4-dithiafulven-6-yl)thiophene | 141198-33-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2,5-bis(1,4-dithiafulven-6-yl)thiophene
• 英文别名: 2-[[5-(1,3-Dithiol-2-ylidenemethyl)thiophen-2-yl]methylidene]-1,3-dithiole
• CAS: 141198-33-6
• 化学式: C₁₂H₈S₅
• 分子量: 312.526
• InChiKey: IHPDAXNZDNNKRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,5-噻吩二甲醛 、 [1,3]Dithiol-2-ylidene-triphenyl-λ⁵-phosphane 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以75%的产率得到2,5-bis(1,4-dithiafulven-6-yl)thiophene
  参考文献：
  名称：

  2,5-Bis(1,4-dithiafulven-6-yl) furans, thiophenes and N-methyl pyrroles as extended analogues of tetrathiafulvalene

  摘要：

  The title compounds are synthesized by Wittig or Wittig-Horner reactions between the corresponding furan, thiophen and N-methyl-pyrrole-2,5-dicarbaldehydes and P-reagents W or P bearing the 1,3-dithiol-2-ylidene moiety adequately substituted al the 4,5-positions; thanks to usual and thin layer cyclic voltammetry, they are shown to possess good pi-donor abilities.

  DOI：

  10.1016/s0040-4039(00)79014-9

文献信息

• Conjugation-Extended Tetrathiafulvalene Analogues Involving a Central Aromatic 5-Membered Heterocyclic Linking Group
  作者：Kazuko Takahashi、Takayasu Nihira、Masaaki Yoshifuji、Kensuke Tomitani

  DOI：10.1246/bcsj.66.2330

  日期：1993.8

  Conjugation-extended tetrathiafulvalene analogues, 2,5-bis(1,4-dithiafulven-6-yl)thiophene (2a), 2,5-bis[2,3-bis(methoxycarbonyl)-1,4-dithiafulven-6-yl]thiophene, and 2,5-bis(1,4-dithiafulven-6-yl)furan, involving an aromatic heterocyclic linking group have been synthesized by the Wittig condensation reaction of 2,5-thiophene- and 2,5-furandicarbaldehydes with 1,3-dithiol-2-ylidenetributylphosphorane and its 4,5-bis(methoxycarbonyl) derivative. The electrochemical redox properties of these compounds in solution have been investigated by cyclic voltammetry in order to evaluate the effect of the linking group on the donating ability and the thermodynamic stability of the radical cations. Whereas the radical cations are not so stable, complexes of 2a with 2,3-dichloro-5,6-dicyano-p-benzoquinone and iodine were found to show relatively high conductivities ((1.0—1.1) × 10−3 S cm−1) on a compressed pellet at room temperature.

  2,5-双(1,4-二硫杂富烯-6-基)噻吩(2a)、2,5-双[2,3-双(甲氧基羰基)-1,4-二硫杂富烯-6-基]噻吩和 2,5-双(1,4-二硫杂富烯-6-基)呋喃的共轭扩展四硫杂富烯类似物、通过 2,5- 噻吩和 2,5- 呋喃二羰基醛与 1,3- 二硫醇-2-亚基四丁基磷烷及其 4,5- 双（甲氧基羰基）衍生物的维蒂希缩合反应，合成了涉及芳香杂环连接基团的 2,5- 噻吩和 2,5-呋喃二羰基醛。通过循环伏安法研究了这些化合物在溶液中的电化学氧化还原特性，以评估连接基团对自由基阳离子的捐献能力和热力学稳定性的影响。2a 与 2,3-二氯-5,6-二氰基对苯醌和碘的配合物在室温下的压缩颗粒上显示出相对较高的电导率（(1.0-1.1) × 10-3 S cm-1），而自由基阳离子则不太稳定。
• Hansen, Thomas K.; Lakshmikantham; Cava, Nichael P., Journal of the American Chemical Society, 1992, vol. 114, # 13, p. 5035 - 5039
  作者：Hansen, Thomas K.、Lakshmikantham、Cava, Nichael P.、Niziurski-Mann, Renée E.、Jensen, Frank、Becher, Jan

  DOI：——

  日期：——
• 2,5-Bis(1,4-dithiafulven-6-yl) furans, thiophenes and N-methyl pyrroles as extended analogues of tetrathiafulvalene
  作者：A.S. Benahmed-Gasmi、P. Frère、B. Garrigues、A. Gorgues、M. Jubault、R. Carlier、F. Texier

  DOI：10.1016/s0040-4039(00)79014-9

  日期：1992.10

  The title compounds are synthesized by Wittig or Wittig-Horner reactions between the corresponding furan, thiophen and N-methyl-pyrrole-2,5-dicarbaldehydes and P-reagents W or P bearing the 1,3-dithiol-2-ylidene moiety adequately substituted al the 4,5-positions; thanks to usual and thin layer cyclic voltammetry, they are shown to possess good pi-donor abilities.