8-chloro-4-oxo-4H-benzo[1,2-d:5,4-d']bis([1,2,3]dithiazole)-2-ium chloride | 1354649-18-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 8-chloro-4-oxo-4H-benzo[1,2-d:5,4-d']bis([1,2,3]dithiazole)-2-ium chloride
• CAS: 1354649-18-5
• 化学式: C₆ClN₂OS₄*Cl
• 分子量: 315.249
• InChiKey: VQJLWRMMNBMHNR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.28
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.85
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  8-chloro-4-oxo-4H-benzo[1,2-d:5,4-d']bis([1,2,3]dithiazole)-2-ium chloride 在 双(四甲基环戊二烯)铁 作用下， 以 乙腈 、 丙腈 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Semiquinone-Bridged Bisdithiazolyl Radicals as Neutral Radical Conductors

  摘要：

  Semiquinone-bridged bisdithiazolyls 3 represent a new class of resonance-stabilized neutral radical for use in the design of single-component conductive materials. As such, they display electrochemical cell potentials lower than those of related pyridine-bridged bisdithiazolyls, a finding which heralds a reduced on-site Coulomb repulsion U. Crystallographic characterization of the chloro-substituted derivative 3a and its acetonitrile solvate 3a center dot MeCN, both of which crystallize in the polar orthorhombic space group Pna2(1), revealed the importance of intermolecular oxygen-to-sulfur (CO center dot center dot center dot SN) interactions in generating rigid, tightly packed radical pi-stacks, including the structural motif found for 3a center dot MeCN in which radicals in neighboring pi-stacks are locked into slipped-ribbon-like arrays. This architecture gives rise to strong intra- and interstack overlap and hence a large electronic bandwidth W. Variable-temperature conductivity measurements on 3a and 3a center dot MeCN indicated high values of sigma(300 K) (>10(-3) S cm(-1)) with correspondingly low thermal activation energies E-act, reaching 0.11 eV in the case of 3a center dot MeCN. Overall, the strong performance of these materials as f = 1/2 conductors is attributed to a combination of low U and large W. Variable-temperature magnetic susceptibility measurements were performed on both 3a and 3a center dot MeCN. The unsolvated material 3a orders as a spincanted antiferromagnet at 8 K, with a canting angle phi = 0.14 degrees and a coercive field H-c = 80 Oe at 2 K.

  DOI：

  10.1021/ja209841z
• 作为产物：
  描述：

  2,6-diamino-4-chlorophenol bishydrochloride 在 二氯化二硫 作用下， 以 乙腈 为溶剂， 生成 8-chloro-4-oxo-4H-benzo[1,2-d:5,4-d']bis([1,2,3]dithiazole)-2-ium chloride
  参考文献：
  名称：

  Semiquinone-Bridged Bisdithiazolyl Radicals as Neutral Radical Conductors

  摘要：

  Semiquinone-bridged bisdithiazolyls 3 represent a new class of resonance-stabilized neutral radical for use in the design of single-component conductive materials. As such, they display electrochemical cell potentials lower than those of related pyridine-bridged bisdithiazolyls, a finding which heralds a reduced on-site Coulomb repulsion U. Crystallographic characterization of the chloro-substituted derivative 3a and its acetonitrile solvate 3a center dot MeCN, both of which crystallize in the polar orthorhombic space group Pna2(1), revealed the importance of intermolecular oxygen-to-sulfur (CO center dot center dot center dot SN) interactions in generating rigid, tightly packed radical pi-stacks, including the structural motif found for 3a center dot MeCN in which radicals in neighboring pi-stacks are locked into slipped-ribbon-like arrays. This architecture gives rise to strong intra- and interstack overlap and hence a large electronic bandwidth W. Variable-temperature conductivity measurements on 3a and 3a center dot MeCN indicated high values of sigma(300 K) (>10(-3) S cm(-1)) with correspondingly low thermal activation energies E-act, reaching 0.11 eV in the case of 3a center dot MeCN. Overall, the strong performance of these materials as f = 1/2 conductors is attributed to a combination of low U and large W. Variable-temperature magnetic susceptibility measurements were performed on both 3a and 3a center dot MeCN. The unsolvated material 3a orders as a spincanted antiferromagnet at 8 K, with a canting angle phi = 0.14 degrees and a coercive field H-c = 80 Oe at 2 K.

  DOI：

  10.1021/ja209841z