2,7-Bis(dicyanomethyl)benzo<2,1-b:3,4-b'>dithiophene | 156355-44-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2,7-Bis(dicyanomethyl)benzo<2,1-b:3,4-b'>dithiophene
• 英文别名: 2-[2-(Dicyanomethyl)thieno[3,2-g][1]benzothiol-7-yl]propanedinitrile
• CAS: 156355-44-1
• 化学式: C₁₆H₆N₄S₂
• 分子量: 318.382
• InChiKey: DHNVVWPTENSEBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  2,7-Bis(dicyanomethyl)benzo<2,1-b:3,4-b'>dithiophene 在 溴 作用下， 以 乙腈 为溶剂， 以47%的产率得到2,7-Bis(dicyanomethylene)-2,7-dihydrobenzo<2,1-b:3,4-b'>dithiophene
  参考文献：
  名称：

  Novel Electron Acceptors Bearing a Heteroquinonoid System. 4. Syntheses, Properties, and Charge-Transfer Complexes of 2,7-Bis(dicyanomethylene)-2,7-dihydrobenzo[2,1-b:3,4-b']dithiophene, 2,7-Bis(dicyanomethylene)-2,7-dihydrobenzo[1,2-b:4,3-b']dithiophene, and 2,6-Bis(dicyanomethylene)-2,6-dihydrobenzo[1,2-b:4,5-b']dithiophene

  摘要：

  The three title compounds were prepared as novel hetero-TCNQ electron accepters comprising the quinonoid skeletons of different benzodithiophene types between two dicyanomethylene groups. On the basis of cyclic voltammetry, they have electron affinities comparable to or stronger than that of TCNQ. In addition, the extensive building blocks serve to induce the effective reduction of on-site coulombic repulsion. They thus behaved as superior electron accepters for forming electrically conductive charge-transfer complexes. In particular, 2,7-bis(dicyanomethylene)-2,7-dihydrobenzo-[2,1-b:3,4-b']dithiophene was the most tractable in terms of stability and solubility, giving a variety of conductive complexes with typical electron donors of TTT, TTF,and TPBP types. Most of these complexes showed a characteristic broad electronic transition in the infrared region of 2.9-4.0 kcm(-1), supporting the idea that their crystal structures assume a stacking form of segregated donor and acceptor columns with mixed valence states.

  DOI：

  10.1021/jo00090a027
• 作为产物：
  描述：

  benzo[2,1-b:3,4-b']dithiophene 在 四(三苯基膦)钯 正丁基锂 、 四甲基乙二胺 、 碘 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 16.17h， 生成 2,7-Bis(dicyanomethyl)benzo<2,1-b:3,4-b'>dithiophene
  参考文献：
  名称：

  Novel Electron Acceptors Bearing a Heteroquinonoid System. 4. Syntheses, Properties, and Charge-Transfer Complexes of 2,7-Bis(dicyanomethylene)-2,7-dihydrobenzo[2,1-b:3,4-b']dithiophene, 2,7-Bis(dicyanomethylene)-2,7-dihydrobenzo[1,2-b:4,3-b']dithiophene, and 2,6-Bis(dicyanomethylene)-2,6-dihydrobenzo[1,2-b:4,5-b']dithiophene

  摘要：

  The three title compounds were prepared as novel hetero-TCNQ electron accepters comprising the quinonoid skeletons of different benzodithiophene types between two dicyanomethylene groups. On the basis of cyclic voltammetry, they have electron affinities comparable to or stronger than that of TCNQ. In addition, the extensive building blocks serve to induce the effective reduction of on-site coulombic repulsion. They thus behaved as superior electron accepters for forming electrically conductive charge-transfer complexes. In particular, 2,7-bis(dicyanomethylene)-2,7-dihydrobenzo-[2,1-b:3,4-b']dithiophene was the most tractable in terms of stability and solubility, giving a variety of conductive complexes with typical electron donors of TTT, TTF,and TPBP types. Most of these complexes showed a characteristic broad electronic transition in the infrared region of 2.9-4.0 kcm(-1), supporting the idea that their crystal structures assume a stacking form of segregated donor and acceptor columns with mixed valence states.

  DOI：

  10.1021/jo00090a027

文献信息

• Novel Electron Acceptors Bearing a Heteroquinonoid System. 4. Syntheses, Properties, and Charge-Transfer Complexes of 2,7-Bis(dicyanomethylene)-2,7-dihydrobenzo[2,1-b:3,4-b']dithiophene, 2,7-Bis(dicyanomethylene)-2,7-dihydrobenzo[1,2-b:4,3-b']dithiophene, and 2,6-Bis(dicyanomethylene)-2,6-dihydrobenzo[1,2-b:4,5-b']dithiophene
  作者：Shu Yoshida、Masanori Fujii、Yoshio Aso、Tetsuo Otsubo、Fumio Ogura

  DOI：10.1021/jo00090a027

  日期：1994.6

  The three title compounds were prepared as novel hetero-TCNQ electron accepters comprising the quinonoid skeletons of different benzodithiophene types between two dicyanomethylene groups. On the basis of cyclic voltammetry, they have electron affinities comparable to or stronger than that of TCNQ. In addition, the extensive building blocks serve to induce the effective reduction of on-site coulombic repulsion. They thus behaved as superior electron accepters for forming electrically conductive charge-transfer complexes. In particular, 2,7-bis(dicyanomethylene)-2,7-dihydrobenzo-[2,1-b:3,4-b']dithiophene was the most tractable in terms of stability and solubility, giving a variety of conductive complexes with typical electron donors of TTT, TTF,and TPBP types. Most of these complexes showed a characteristic broad electronic transition in the infrared region of 2.9-4.0 kcm(-1), supporting the idea that their crystal structures assume a stacking form of segregated donor and acceptor columns with mixed valence states.