4,8-Bis-benzo[1,3]dithiol-2-ylidene-4H,8H-benzo[1,2-c;4,5-c']bis[1,2,5]thiadiazole | 115820-63-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 英文名称: 4,8-Bis-benzo[1,3]dithiol-2-ylidene-4H,8H-benzo[1,2-c;4,5-c']bis[1,2,5]thiadiazole
• 英文别名: 4,8-Bis(1,3-benzodithiol-2-ylidene)-[1,2,5]thiadiazolo[3,4-f][2,1,3]benzothiadiazole
• CAS: 115820-63-8
• 化学式: C₂₀H₈N₄S₆
• 分子量: 496.706
• InChiKey: YIDSFBFUFQTVJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  209
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4,8-Bis-benzo[1,3]dithiol-2-ylidene-4H,8H-benzo[1,2-c;4,5-c']bis[1,2,5]thiadiazole 在 碘 作用下， 反应 48.0h， 生成 4,8-Bis-benzo[1,3]dithiol-2-ylidene-4H,8H-benzo[1,2-c;4,5-c']bis[1,2,5]thiadiazole; compound with iodine
  参考文献：
  名称：

  Preparation and properties of bis[1,2,5]thiadiazolo-p-quinobis(1,3-dithiole) (BTQBT) and its derivatives. Novel organic semiconductors

  摘要：

  Bis[1,2,5]thiadiazlo-p-quinobis(1,3-dithiole) (BTQBT) (3a) and its derivatives 3b-f were prepared by using a Wittig-Horner reaction. The conductivity of BTQBT was good as a single component. The X-ray structural analysis reveals that the planar molecule forms a sheetlike network by short S---S contacts. The conductivities of the derivatives 3b-f were poorer than that of BTQBT, indicating that the unique crystal structure of BTQBT is needed for the good conductivity. The selenadiazolo analogues 9a,b were also prepared. The conductivities were a little higher than that of BTQBT due to the stronger intermolecular interactions caused by the selenium atom.

  DOI：

  10.1021/jo00046a039
• 作为产物：
  描述：

  1,3-苯并二硫醇-2-基膦酸二甲酯 、 4H,8H-benzo<1,2-c:4,5-c'>bis<1,2,5>thiadiazole-4,8-dione 在 正丁基锂 作用下， 以50%的产率得到4,8-Bis-benzo[1,3]dithiol-2-ylidene-4H,8H-benzo[1,2-c;4,5-c']bis[1,2,5]thiadiazole
  参考文献：
  名称：

  稠合至 1,2,5-噻二唑单元和相关杂环的喹二甲烷四硫代衍生物的制备和性质

  摘要：

  2-二甲氧基膦酰基-1,3-苯二硫醇与稠合到 1,2,5-噻二唑单元和相关杂环的 1,4-苯醌的 Wittig-Horner 反应产生了一种新型供体，其显示出可逆的双电子氧化波并形成碘和 DDQ 的导电络合物。

  DOI：

  10.1246/cl.1988.661

文献信息

• Preparation and Properties of Tetrathio-derivatives of Quinodimethanes Fused to a 1,2,5-Thiadiazole Unit and Related Heterocycles
  作者：Yoshiro Yamashita、Tsutomu Miyashi

  DOI：10.1246/cl.1988.661

  日期：1988.4.5

  Wittig-Horner reaction of 2-dimethoxyphosphinyl-1,3-benzodithiole with 1,4-benzoquinones fused to a 1,2,5-thiadiazole unit and related heterocycles gave a new type of donors which show reversible two-electron oxidation waves and formed conductive complexes with iodine and DDQ.

  2-二甲氧基膦酰基-1,3-苯二硫醇与稠合到 1,2,5-噻二唑单元和相关杂环的 1,4-苯醌的 Wittig-Horner 反应产生了一种新型供体，其显示出可逆的双电子氧化波并形成碘和 DDQ 的导电络合物。
• YAMASHITA, YOSHIRO;MIYASHI, TSUTOMU, CHEM. LETT.,(1988) N 4, 661-664
  作者：YAMASHITA, YOSHIRO、MIYASHI, TSUTOMU

  DOI：——

  日期：——
• Yamashita, Yoshiro; Tanaka, Shoji; Imaeda, Kenichi, Chemistry Letters, 1991, p. 1213 - 1216
  作者：Yamashita, Yoshiro、Tanaka, Shoji、Imaeda, Kenichi、Inokuchi, Hiroo

  DOI：——

  日期：——
• Preparation and properties of bis[1,2,5]thiadiazolo-p-quinobis(1,3-dithiole) (BTQBT) and its derivatives. Novel organic semiconductors
  作者：Yoshiro Yamashita、Shoji Tanaka、Kenichi Imaeda、Hiroo Inokuchi、Mizuka Sano

  DOI：10.1021/jo00046a039

  日期：1992.9

  Bis[1,2,5]thiadiazlo-p-quinobis(1,3-dithiole) (BTQBT) (3a) and its derivatives 3b-f were prepared by using a Wittig-Horner reaction. The conductivity of BTQBT was good as a single component. The X-ray structural analysis reveals that the planar molecule forms a sheetlike network by short S---S contacts. The conductivities of the derivatives 3b-f were poorer than that of BTQBT, indicating that the unique crystal structure of BTQBT is needed for the good conductivity. The selenadiazolo analogues 9a,b were also prepared. The conductivities were a little higher than that of BTQBT due to the stronger intermolecular interactions caused by the selenium atom.