2,6-dicyanomethylene-4-ethylenedioxy-2,6-dihydrocyclopenta[2,1-b;3,4-b']dithiophene | 691411-95-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-dicyanomethylene-4-ethylenedioxy-2,6-dihydrocyclopenta[2,1-b;3,4-b']dithiophene
• CAS: 691411-95-7
• 化学式: C₁₇H₆N₄O₂S₂
• 分子量: 362.392
• InChiKey: GKCVCABGAPZYEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.05
• 重原子数：
  25.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  113.62
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2,6-dicyanomethylene-4-ethylenedioxy-2,6-dihydrocyclopenta[2,1-b;3,4-b']dithiophene 在 高氯酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 以96%的产率得到2,6-dicyanomethylene-4-oxo-2,6-dihydrocyclopenta[2,1-b;3,4-b']dithiophene
  参考文献：
  名称：

  Synthesis, Crystal Structures, and Electrical Properties of Anion Radical Salts of Novel Electron Acceptors, 2,6-Dicyanomethylene-4-oxo-2,6-dihydrocyclopentadithiophene (CPDT-TCNQ) and Its Diselenophene Analogue (CPDS-TCNQ), Having Three Electron-Withdrawing Groups

  摘要：

  ion离子。

  DOI：

  10.1246/bcsj.77.463
• 作为产物：
  描述：

  spiro[4H-cyclopenta[2,1-b;3,4-b']-dithiophene-4,2'-[1,3]dioxolan] 在 四(三苯基膦)钯 正丁基锂 、 水 、 溴 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 2,6-dicyanomethylene-4-ethylenedioxy-2,6-dihydrocyclopenta[2,1-b;3,4-b']dithiophene
  参考文献：
  名称：

  Crystal structures and electrical conducting properties of the first molecular metals based on a novel electron acceptor, 4-oxo-2,6-bis(dicyanomethylene)-2,6-dihydrocyclopentadithiophene (CPDT)

  摘要：

  一种新型电子受体CPDT已经合成；CPDT金属阴离子自由基盐的费米表面是纯一维的，而受体分子在盐的晶体结构中形成刚性且紧密的二维网络。

  DOI：

  10.1039/a801500g

文献信息

• Synthesis, Crystal Structures, and Electrical Properties of Anion Radical Salts of Novel Electron Acceptors, 2,6-Dicyanomethylene-4-oxo-2,6-dihydrocyclopentadithiophene (CPDT-TCNQ) and Its Diselenophene Analogue (CPDS-TCNQ), Having Three Electron-Withdrawing Groups
  作者：Shinji Tarutani、Kazuko Takahashi

  DOI：10.1246/bcsj.77.463

  日期：2004.3

  Novel heterophene analogues of tetracyanodiphenoquinodimethane (TCNDQ) having three electron-withdrawing groups in one molecule, 2,6-dicyanomethylene-4-oxo-2,6-dihydrocyclopentadithiophene (CPDT-TCNQ: 1) and 2,6-dicyanomethylene-4-oxo-2,6-dihydrocyclopentadiselenophene (CPDS-TCNQ: 2), have been synthesized. CPDT-TCNQ and CPDS-TCNQ have a good coplanar conformation and have a fairly high electron-accepting ability due to the existence of the central carbonyl group in addition to the two terminal dicyanomethylene groups. The anion radical salts, Me4X(CPDT-TCNQ)2 (X = N, P, and As), Et4N(CPDT-TCNQ)2, and Me4X(CPDS-TCNQ)2 (X = P and As), showed a metallic conducting behavior (σrt = 260 to 42 S cm−1) down to 130–255 K. In the crystal structures of Me4X(CPDT-TCNQ)2 (X = N, P, and As), which are isostructural with each other, the acceptor molecules form rigid and tight two-dimensional networks consisting of strong S···N and O···H inter-column contacts in the side-by-side direction. However, these salts have an extremely one-dimensional electronic structure along the stacking direction. This fact indicates that the chalcogen atoms in the acceptor molecules do not increase the dimensionality of the electronic structures of the anion radical salts; that property is significantly different from the role of chalcogen atoms of TTF or BEDT-TTF type donor molecules. The existence of the central carbonyl group in CPDT-TCNQ and in CPDS-TCNQ plays a very important role to give metallic anion radical salts due to the rigid conformation. The phase transition at 130 K on Me4N(CPDT-TCNQ)2 is regarded as 2kF CDW instability. The origins of the phase transitions at 165 K for Me4P(CPDT-TCNQ)2 and 185 K for Me4As(CPDT-TCNQ)2 are regarded as 4kF CDW. Thus the phase transition mechanisms of these salts are significantly different from each other, although the crystal structures are isostructural.

  ion离子。
• Crystal structures and electrical conducting properties of the first molecular metals based on a novel electron acceptor, 4-oxo-2,6-bis(dicyanomethylene)-2,6-dihydrocyclopentadithiophene (CPDT)
  作者：Kazuko Takahashi、Shinji Tarutani

  DOI：10.1039/a801500g

  日期：——

  A novel electron acceptor CPDT has been synthesized; the Fermi surfaces of the metallic anion radical salts of CPDT are purely one-dimensional, while the acceptor molecules form rigid and tight two-dimensional networks in the crystal structures of the salts.

  一种新型电子受体CPDT已经合成；CPDT金属阴离子自由基盐的费米表面是纯一维的，而受体分子在盐的晶体结构中形成刚性且紧密的二维网络。