5,5’-bis(2-thienyl)-2,2’-bifuran | 1445682-79-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 5,5’-bis(2-thienyl)-2,2’-bifuran
• 英文别名: 2-Thiophen-2-yl-5-(5-thiophen-2-ylfuran-2-yl)furan；2-thiophen-2-yl-5-(5-thiophen-2-ylfuran-2-yl)furan
• CAS: 1445682-79-0
• 化学式: C₁₆H₁₀O₂S₂
• 分子量: 298.386
• InChiKey: KRHZXEKYYLDCBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,2'-联呋喃 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 水 、 苯 为溶剂， 反应 12.0h， 生成 5,5’-bis(2-thienyl)-2,2’-bifuran
  参考文献：
  名称：

  Bifurans via Palladium-Catalyzed Suzuki Coupling

  摘要：

  Sixteen 2,2'-bifurans with aryl substituents are reported. The copper-mediated oxidative coupling of lithium salt of furan led to the formation of 2,2'-bifuran, which was brominated with either 2 eq. or 4 eq. NBS to afford 5,5 '-dibromo-2,2'-bifuran and 3,3',5,5'-tetrabromo-2,2'-bifuran. The palladium-catalyzed Suzuki reactions between dibromo or tetrabormo-bifuran and arylboronic acid were employed to furnish the title compounds, which were characterized by NMR spectra and mass spectra.

  DOI：

  10.3987/com-15-13318

文献信息

• Study of a bifuran vs. bithiophene unit for the rational design of π-conjugated systems. What have we learned?
  作者：Ori Gidron、Neta Varsano、Linda J. W. Shimon、Gregory Leitus、Michael Bendikov

  DOI：10.1039/c3cc41795f

  日期：——

  A comparative study of two structural isomers highlights the advantages of bifuran vs. bithiophene units in conjugated systems, such as higher fluorescence, solubility, and increased stability of the oxidized species. Importantly, we have found that the small bifuran unit bestows the advantages found in longer oligofurans, and should be considered in the rational design of π-conjugated systems.

  对两种结构异构体的比较研究凸显了联呋喃与联噻吩单元在共轭体系中的优势，例如更高的荧光、溶解度和氧化物种的稳定性。重要的是，我们发现，较小的联呋喃单元具有较长的寡联呋喃单元的优势，在Β-共轭体系的合理设计中应予以考虑。
• Bifurans via Palladium-Catalyzed Suzuki Coupling
  作者：Qiancai Liu、Jun Zhang、Peijun Ye、Lu He、Ting Yuan

  DOI：10.3987/com-15-13318

  日期：——

  Sixteen 2,2'-bifurans with aryl substituents are reported. The copper-mediated oxidative coupling of lithium salt of furan led to the formation of 2,2'-bifuran, which was brominated with either 2 eq. or 4 eq. NBS to afford 5,5 '-dibromo-2,2'-bifuran and 3,3',5,5'-tetrabromo-2,2'-bifuran. The palladium-catalyzed Suzuki reactions between dibromo or tetrabormo-bifuran and arylboronic acid were employed to furnish the title compounds, which were characterized by NMR spectra and mass spectra.