1,2-bis(benzo[b]thiophen-3-yl)benzene | 1347708-09-1

• 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: 1,2-bis(benzo[b]thiophen-3-yl)benzene
• 英文别名: 1,2-bis(benzo[b]thien-3-yl)benzene；1,2-bis(3-benzo[b]thienyl)benzene；3-[2-(1-Benzothiophen-3-yl)phenyl]-1-benzothiophene；3-[2-(1-benzothiophen-3-yl)phenyl]-1-benzothiophene
• CAS: 1347708-09-1
• 化学式: C₂₂H₁₄S₂
• 分子量: 342.485
• InChiKey: RVPCMAGDXMEZNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-bis(benzo[b]thiophen-3-yl)benzene 在 五氯化钼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以75%的产率得到naphtho[2,1-b:3,4-b']bis[1]benzothiophene
  参考文献：
  名称：

  使用钼 (V) 试剂对噻吩衍生物进行 CH 活化介导的氧化（交叉）偶联反应

  摘要：

  通过使用五氯化钼进行氧化偶联，可以快速、模块化地获得高产率的复杂噻吩并。偶联过程可以用噻吩和苯并噻吩衍生物完成，并提供各种复杂的骨架，如螺环化合物。在这种方法中，建立了第一个使用 MoCl5 的交叉偶联反应，并合成了半导体材料的重要基序。

  DOI：

  10.1002/ejoc.201403188
• 作为产物：
  描述：

  1,2-二碘苯 、 (benzo[b]thiophen-3-yl)trimethylstannane 在 copper(l) iodide 、 四(三苯基膦)钯 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以45%的产率得到1,2-bis(benzo[b]thiophen-3-yl)benzene
  参考文献：
  名称：

  Synthesis, Crystal Structures, and Electronic Properties of Nonlinear Fused Thienoacene Semiconductors

  摘要：

  Two fused thienoacene compounds with two-dimensional ring connectivity were synthesized, and their semiconducting properties were characterized. Both compounds have a crystal structure comprised of herringbone arrays of tight pi-pi stacks. Strong pi-pi interactions lead to self-assembly into well-defined crystalline thin films from the vapor phase for both compounds. Field effect transistors were fabricated, affording identical hole mobilities of 3.0 x 10(-3) cm(2)/(V s) and l(on/off) > 10(5).

  DOI：

  10.1021/ol202662s

文献信息

• Oxidative (Cross-)Coupling Reactions Mediated by C-H Activation of Thiophene Derivatives by Using Molybdenum(V) Reagents
  作者：Moritz Schubert、Simon Trosien、Lara Schulz、Carolin Brandscheid、Dieter Schollmeyer、Siegfried R. Waldvogel

  DOI：10.1002/ejoc.201403188

  日期：2014.11

  Oxidative coupling by using molybdenum pentachloride provides fast and modular access to sophisticated thienoacenes in excellent yields. The coupling process can be accomplished with thiophene and benzothiophene derivatives and provides various complex skeletons such as spirocyclic compounds. In this approach, the first cross-coupling reactions with the use of MoCl5 were established and important motifs

  通过使用五氯化钼进行氧化偶联，可以快速、模块化地获得高产率的复杂噻吩并。偶联过程可以用噻吩和苯并噻吩衍生物完成，并提供各种复杂的骨架，如螺环化合物。在这种方法中，建立了第一个使用 MoCl5 的交叉偶联反应，并合成了半导体材料的重要基序。
• Synthesis, Crystal Structures, and Electronic Properties of Nonlinear Fused Thienoacene Semiconductors
  作者：Hayden T. Black、Shubin Liu、Valerie Sheares Ashby

  DOI：10.1021/ol202662s

  日期：2011.12.16

  Two fused thienoacene compounds with two-dimensional ring connectivity were synthesized, and their semiconducting properties were characterized. Both compounds have a crystal structure comprised of herringbone arrays of tight pi-pi stacks. Strong pi-pi interactions lead to self-assembly into well-defined crystalline thin films from the vapor phase for both compounds. Field effect transistors were fabricated, affording identical hole mobilities of 3.0 x 10(-3) cm(2)/(V s) and l(on/off) > 10(5).