5,5'''''''-dihexyl-3''',3''''',4'',4''''-tetrakis(hexylsulphanyl)octithiophene | 1309469-62-2

• 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: 5,5'''''''-dihexyl-3''',3''''',4'',4''''-tetrakis(hexylsulphanyl)octithiophene
• 英文别名: 3-Hexylsulfanyl-2-[3-hexylsulfanyl-5-[4-hexylsulfanyl-5-[3-hexylsulfanyl-5-[5-(5-hexylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]-5-[5-(5-hexylthiophen-2-yl)thiophen-2-yl]thiophene；3-hexylsulfanyl-2-[3-hexylsulfanyl-5-[4-hexylsulfanyl-5-[3-hexylsulfanyl-5-[5-(5-hexylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]-5-[5-(5-hexylthiophen-2-yl)thiophen-2-yl]thiophene
• CAS: 1309469-62-2
• 化学式: C₆₈H₉₀S₁₂
• 分子量: 1292.25
• InChiKey: WOCGXLLCXANJCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  28.3
• 重原子数：
  80
• 可旋转键数：
  41
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  327
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  3-(hexylthio)thiophene 在 N-溴代丁二酰亚胺(NBS) 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 碳酸氢钠 、 联硼酸频那醇酯 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.6h， 生成 5,5'''''''-dihexyl-3''',3''''',4'',4''''-tetrakis(hexylsulphanyl)octithiophene
  参考文献：
  名称：

  A Successful Chemical Strategy To Induce Oligothiophene Self-Assembly into Fibers with Tunable Shape and Function

  摘要：

  Functional supramolecular architectures for bottom-up organic nano- and microtechnology are a high priority research topic. We discovered a new recognition algorithm, resulting from the combination of thioalkyl substituents and head-to-head regiochemistry of substitution, to induce the spontaneous self-assembly of sulfur overrich octathiophenes into supramolecular crystalline fibers combining high charge mobility and intense fluorescence. The fibers were grown on various types of surfaces either as superhelices or straight rods depending on molecular structure. Helical fibers directly grown on a field effect transistor displayed efficient charge mobility and intrinsic 'memory effect'. Despite the fact that the oligomers did not have chirality centers, one type of hand-helicity was always predominant in helical fibers, due to the interplay of molecular atropisomerism and sup ramolecular helicity induced by terminal substituents. Finally, we found that the new sulfur overrich oligothiophenes can easily be prepared in high yields through ultrasound and microwave assistance in green conditions.

  DOI：

  10.1021/ja2014949

文献信息

• A Successful Chemical Strategy To Induce Oligothiophene Self-Assembly into Fibers with Tunable Shape and Function
  作者：Francesca Di Maria、Pasquale Olivelli、Massimo Gazzano、Alberto Zanelli、Mariano Biasiucci、Giuseppe Gigli、Denis Gentili、Pasquale D’Angelo、Massimiliano Cavallini、Giovanna Barbarella

  DOI：10.1021/ja2014949

  日期：2011.6.8

  Functional supramolecular architectures for bottom-up organic nano- and microtechnology are a high priority research topic. We discovered a new recognition algorithm, resulting from the combination of thioalkyl substituents and head-to-head regiochemistry of substitution, to induce the spontaneous self-assembly of sulfur overrich octathiophenes into supramolecular crystalline fibers combining high charge mobility and intense fluorescence. The fibers were grown on various types of surfaces either as superhelices or straight rods depending on molecular structure. Helical fibers directly grown on a field effect transistor displayed efficient charge mobility and intrinsic 'memory effect'. Despite the fact that the oligomers did not have chirality centers, one type of hand-helicity was always predominant in helical fibers, due to the interplay of molecular atropisomerism and sup ramolecular helicity induced by terminal substituents. Finally, we found that the new sulfur overrich oligothiophenes can easily be prepared in high yields through ultrasound and microwave assistance in green conditions.