3-nitro-2-(benzothiophen-2-yl)benzothiophene | 1101752-30-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 3-nitro-2-(benzothiophen-2-yl)benzothiophene
• CAS: 1101752-30-0
• 化学式: C₁₆H₉NO₂S₂
• 分子量: 311.385
• InChiKey: VUBSIWVREGORJS-UHFFFAOYSA-N

物化性质

• 熔点：
  133-135 °C
• 沸点：
  520.4±35.0 °C(Predicted)
• 密度：
  1.456±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.69
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.14
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-nitro-2-(benzothiophen-2-yl)benzothiophene 在 三苯基膦 、 potassium hydroxide 作用下， 以 邻二氯苯 、 丙酮 为溶剂， 生成 N-hexyldibenzothieno[3,2-b:2′,3′-d]pyrrole
  参考文献：
  名称：

  Advantage of arch-shaped structure on transistor performances over linear-shaped structure in dibenzothienopyrrole semiconductors

  摘要：

  To understand the influence of molecular shape on the optoelectronic properties of heteroacenes, we report here the syntheses and characterizations of two linear- and two arch-shaped dibenzothienopyrrole (DBTP) derivatives, namely, N-hexyldibenzothieno[3,2-b:2',3'-d]pyrrole (l-HDBTP), N-phenyldibenzothieno[3,2-b:2',3'-d] pyrrole (l-PDBTP), N-hexyldibenzothieno[2,3-b:3',2'-d]pyrrole (a-HDBTP) and N-phenyldibenzothieno[2,3-b:3',2'-d]pyrrole (a-PDBTP). Their structure-property relationships have been systematically studied by optical absorption, cyclic voltammetry, single-crystal X-ray diffraction analyses and the single-crystal-based and thin-film-based field-effect transistors (FETs). The results demonstrate that the arch-shaped DBTP derivatives can modify their electronic structures and molecular arrangements by tuning of substituents, to obtain a better charge-transporting ability relative to the linear-shaped ones. The arch-shaped N-phenyl substituted a-PDBTP exhibits optimum molecular pi-stacking arrangement and charge transport properties, with the hole mobility of 0.75 cm(2)V(-1)s(-1) and 0.058 cm(2)V(-1)s(-1) for the single-crystal and the thin-film OFETs, respectively. These results indicate that the arch-shaped DBTP core is a promising building block in the area of organic semiconducting materials.

  DOI：

  10.1016/j.orgel.2018.06.044
• 作为产物：
  描述：

  2,2'-bibenzo[b]thiophene 在 硝酸 、 溶剂黄146 作用下， 以97%的产率得到3-nitro-2-(benzothiophen-2-yl)benzothiophene
  参考文献：
  名称：

  二苯并噻吩并[b，d]吡咯的反式和顺式异构体的合成及性质。

  摘要：

  由苯并[b]噻吩有效地合成了由两个噻吩环和一个吡咯环组成的五环化合物的新型反式和顺式异构体，与同式异构体及其氮原子相比，该反式异构体具有更好的电荷传输和OFET性质-己基取代。

  DOI：

  10.1039/b813683a

文献信息

• K₂S₂O₈-mediated radical cyclisation of 2-alkynylthioanisoles or -selenoanisoles: a green and regioselective route to 3-nitrobenzothiophenes and benzoselenophenes
  作者：Shi-Chao Lu、Botao Wu、Shi-Peng Zhang、Ya-Ling Gong、Shu Xu

  DOI：10.1039/d0ra03894f

  日期：——

  An acid, transition-metal, and chromatography-free radical nitration/cyclisation of 2-alkynylthioanisoles or -selenoanisoles has been developed. This is the first example of the use of highly unstable 2-nitrovinyl radicals for C–S bond formation. This facile route efficiently produces 3-nitrobenzothiophenes and benzoselenophenes, which are difficult to access via classical methods. Density functional

  已经开发了 2-炔基硫代苯甲醚或-硒代苯甲醚的酸、过渡金属和色谱自由基硝化/环化。这是使用高度不稳定的 2-硝基乙烯基自由基形成 C-S 键的第一个例子。这种简便的路线有效地生产 3-硝基苯并噻吩和苯并硒吩，这些是通过经典方法难以获得的。进行密度泛函理论（DFT）计算以探索反应机理。对所得产品的体外抗结核活性进行了测试，化合物2d和2l显示出对敏感和耐药菌株的显着活性。