2,6-Bis(dicyanomethyl)benzo<1,2-b:4,5-b'>dithiophene | 155904-21-5

• 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: 2,6-Bis(dicyanomethyl)benzo<1,2-b:4,5-b'>dithiophene
• 英文别名: 2,6-bis(dicyanomethyl)benzo[1,2-b:4,5-b']dithiophene；2-[2-(Dicyanomethyl)thieno[2,3-f][1]benzothiol-6-yl]propanedinitrile
• CAS: 155904-21-5
• 化学式: C₁₆H₆N₄S₂
• 分子量: 318.382
• InChiKey: SPUDFXLCJPHRDT-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：

  2,6-Bis(dicyanomethyl)benzo<1,2-b:4,5-b'>dithiophene 在 水 、 溴 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以48%的产率得到2,6-Bis(dicyanomethylene)-2,6-dihydrobenzo<1,2-b:4,5-b'>dithiophene
  参考文献：
  名称：

  Alkylated 2,6-Bis(dicyanomethylene)-2,6-dihydrobenzo[1,2-b:4,5-b′]dithiophenes: New Soluble n-Channel Organic Semiconductors for Air-stable OFETs

  摘要：

  基于2,6-双(二氰基亚甲基)-2,6-二氢苯并[1,2-b:4,5-b′]二噻吩核，开发了新的可加工n沟道有机半导体。在环境条件下，OFET表现出n沟道晶体管特性，电子场效应迁移率高达6.3×10−3 cm2 V−1 s−1。

  DOI：

  10.1246/cl.2009.568
• 作为产物：
  描述：

  苯并[1,2-b:4,5-b']二噻吩 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， 生成 2,6-Bis(dicyanomethyl)benzo<1,2-b:4,5-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

• Organic electroluminescent materials and devices
  申请人：BEIJING SUMMER SPROUT TECHNOLOGY CO., LTD.

  公开号：US11349080B2

  公开（公告）日：2022-05-31

  Organic electroluminescent materials and devices are disclosed. The organic electroluminescent materials are novel benzodithiophene or its analogous structure compounds, which can be used as charge transporting materials, hole injection materials, or the like in an electroluminescent device. These novel compounds can offer excellent performance compared with existing materials, for example, to further improve the voltage, efficiency and/or lifetime of the OLEDs.

  本文公开了有机电致发光材料和装置。这些有机电致发光材料是新型苯并二噻吩或其类似结构化合物，可用作电致发光器件中的电荷传输材料、空穴注入材料或类似材料。与现有材料相比，这些新型化合物具有优异的性能，例如可进一步提高有机发光二极管的电压、效率和/或寿命。
• ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES
  申请人：Xia Chuanjun

  公开号：US20190181349A1

  公开（公告）日：2019-06-13

  Organic electroluminescent materials and devices are disclosed. The organic electroluminescent materials are novel benzodithiophene or its analogous structure compounds, which can be used as charge transporting materials, hole injection materials, or the like in an electroluminescent device. These novel compounds can offer excellent performance compared with existing materials, for example, to further improve the voltage, efficiency and/or lifetime of the OLEDs.
• 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.
• Alkylated 2,6-Bis(dicyanomethylene)-2,6-dihydrobenzo[1,2-<i>b</i>:4,5-<i>b</i>′]dithiophenes: New Soluble n-Channel Organic Semiconductors for Air-stable OFETs
  作者：Tomoya Kashiki、Eigo Miyazaki、Kazuo Takimiya

  DOI：10.1246/cl.2009.568

  日期：2009.6.5

  New solution-prosessable n-channel organic semiconductors were developed based on a 2,6-bis(dicyanomethylene)-2,6-dihydrobenzo[1,2-b:4,5-b′]dithiophene core. The OFETs showed n-channel transistor characteristics under ambient conditions with electron field-effect mobility up to 6.3×10−3 cm2 V−1 s−1.

  基于2,6-双(二氰基亚甲基)-2,6-二氢苯并[1,2-b:4,5-b′]二噻吩核，开发了新的可加工n沟道有机半导体。在环境条件下，OFET表现出n沟道晶体管特性，电子场效应迁移率高达6.3×10−3 cm2 V−1 s−1。