5-dodecylsulfanyl-2,2'-bithiophene | 444346-19-4

• 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: 5-dodecylsulfanyl-2,2'-bithiophene
• 英文别名: 5-(dodecylthio)-2,2'-bithiophene；2-Dodecylsulfanyl-5-thiophen-2-ylthiophene
• CAS: 444346-19-4
• 化学式: C₂₀H₃₀S₃
• 分子量: 366.656
• InChiKey: XKZPOCFHYVEQHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  81.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-dodecylsulfanyl-2,2'-bithiophene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以90%的产率得到5-bromo-5'-dodecylsulfanyl-2,2'-bithiophene
  参考文献：
  名称：

  Synthesis and optical properties of soluble sexithiophenes with one central head-to-head junction

  摘要：

  The regioselective synthesis of three sexithiophenes characterized by the presence of one central 3,3'-dimethyl-2,2'-bithiophene subsystem is described. One of these compounds was obtained under mild conditions by microwave-mediated synthesis. All sexithiophenes were soluble in organic solvents and displayed 30-40% fluorescence quantum yields in solution. In thin films the fluorescence quantum yields dropped to 1-2%, indicating conformational changes and strong intermolecular interactions in the solid state. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00098-4
• 作为产物：
  描述：

  5-溴-2,2-双噻吩 在 正丁基锂 、 potassium tert-butylate 作用下， 以 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.66h， 生成 5-dodecylsulfanyl-2,2'-bithiophene
  参考文献：
  名称：

  Synthesis and optical properties of soluble sexithiophenes with one central head-to-head junction

  摘要：

  The regioselective synthesis of three sexithiophenes characterized by the presence of one central 3,3'-dimethyl-2,2'-bithiophene subsystem is described. One of these compounds was obtained under mild conditions by microwave-mediated synthesis. All sexithiophenes were soluble in organic solvents and displayed 30-40% fluorescence quantum yields in solution. In thin films the fluorescence quantum yields dropped to 1-2%, indicating conformational changes and strong intermolecular interactions in the solid state. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00098-4

文献信息

• End-Capping Groups for Small-Molecule Organic Semiconducting Materials: Synthetic Investigation and Photovoltaic Applications through Direct C-H (Hetero)arylation
  作者：Te-Jui Lu、Po-Han Lin、Kun-Mu Lee、Ching-Yuan Liu

  DOI：10.1002/ejoc.201601257

  日期：2017.1.3

  A Pd-catalyzed C–H (hetero)arylation methodology has been optimized for the efficient synthesis of various useful end-capping groups that are widely applied in small-molecule optoelectronic materials. We report herein the synthesis of a broad scope of target molecules ranging from donor-type through acceptor-type to hybrid-type end-capping groups. To demonstrate their application in dye-sensitized

  Pd催化的C-H（杂）芳基化方法已被优化用于有效合成广泛应用于小分子光电材料的各种有用的封端基团。我们在此报告了范围广泛的目标分子的合成，范围从供体型到受体型到混合型封端基团。为了证明它们在染料敏化太阳能电池中的应用，我们设计了两种新的 D-A-π-A' 型有机敏化剂（CYL-3 和 CYL-4），它们是通过连续 C -H 芳基化使用容易获得的封端基团。基于 CYL-3 和 CYL-4 的器件的 Voc 值为 0.67–0.71 V，Jsc 值为 10.07–11.63 mA cm–2，FF 值为 70.6–72.9 %，对应的总功率转换效率为 4.76– 6.02%。