2,5'-bithieno[3,2-b]furan | 1401441-35-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2,5'-bithieno[3,2-b]furan
• 英文别名: 2,5'-Bithieno[3,2-b]furan；2-thieno[3,2-b]furan-5-ylthieno[3,2-b]furan
• CAS: 1401441-35-7
• 化学式: C₁₂H₆O₂S₂
• 分子量: 246.31
• InChiKey: YGHIAFUSKHXTOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  1
• 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：

  thieno[3,2-b]furan 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 2,5'-bithieno[3,2-b]furan
  参考文献：
  名称：

  Regiochemical Effects of Furan Substitution on the Electronic Properties and Solid-State Structure of Partial Fused-Ring Oligothiophenes

  摘要：

  Oligomers containing the new fused-ring heterocyclic conjugated building block thieno[3,2-b]furan were synthesized, and the effects associated with furan ring substitution into fused-ring oligothiophenes on the electronic properties and solid-state structure were assessed. A series of four ring oligomers which vary in. the degree of furan ring substitution and the regiochemistry of placement were synthesized via Stille cross coupling and oxidative homocoupling strategies. The electronic properties of these oligomers were studied by UV-vis absorption and fluorescence spectroscopies. Substitution of furan rings at the terminal positions yields oligomers with a narrower HOMO-LUMO gap relative to the all-thiophene analogue 2,2'-bithieno[3,2-b]thiophene, and incorporation of furan rings at the interior positions results in oligomers with an increase in rigidity and a higher fluorescence quantum yield. Packing motifs of the oligomers were determined using single crystal X-ray diffraction. In contrast to the herringbone crystal packing observed for nonfused oligothiophenes, oligofurans, thiophene-furan hybrid oligomers, and the all-thiophene analogue 2,2'-bithieno[3,2-b]thiophene, all three regioisomers derived from the dimerization of thieno[3,2-b]furan arrange in a pi-stacked packing motif in the solid state.

  DOI：

  10.1021/jo301744s

文献信息

• Regiochemical Effects of Furan Substitution on the Electronic Properties and Solid-State Structure of Partial Fused-Ring Oligothiophenes
  作者：John T. Henssler、Adam J. Matzger

  DOI：10.1021/jo301744s

  日期：2012.10.19

  Oligomers containing the new fused-ring heterocyclic conjugated building block thieno[3,2-b]furan were synthesized, and the effects associated with furan ring substitution into fused-ring oligothiophenes on the electronic properties and solid-state structure were assessed. A series of four ring oligomers which vary in. the degree of furan ring substitution and the regiochemistry of placement were synthesized via Stille cross coupling and oxidative homocoupling strategies. The electronic properties of these oligomers were studied by UV-vis absorption and fluorescence spectroscopies. Substitution of furan rings at the terminal positions yields oligomers with a narrower HOMO-LUMO gap relative to the all-thiophene analogue 2,2'-bithieno[3,2-b]thiophene, and incorporation of furan rings at the interior positions results in oligomers with an increase in rigidity and a higher fluorescence quantum yield. Packing motifs of the oligomers were determined using single crystal X-ray diffraction. In contrast to the herringbone crystal packing observed for nonfused oligothiophenes, oligofurans, thiophene-furan hybrid oligomers, and the all-thiophene analogue 2,2'-bithieno[3,2-b]thiophene, all three regioisomers derived from the dimerization of thieno[3,2-b]furan arrange in a pi-stacked packing motif in the solid state.