5,6-di(p-tolyl)indolo[3,2-b:4,5-b']thiophene | 1027351-73-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5,6-di(p-tolyl)indolo[3,2-b:4,5-b']thiophene
• 英文别名: 3,19-Bis(4-methylphenyl)-11-thia-3,19-diazapentacyclo[10.7.0.02,10.04,9.013,18]nonadeca-1(12),2(10),4,6,8,13,15,17-octaene
• CAS: 1027351-73-0
• 化学式: C₃₀H₂₂N₂S
• 分子量: 442.584
• InChiKey: NRDYIEKUHQBLFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3,3'-dibromo-1,1'-di(p-tolyl)-1H,1'H-2,2'-biindole 在 正丁基锂 、 双(苯磺酰)硫醚 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以55%的产率得到5,6-di(p-tolyl)indolo[3,2-b:4,5-b']thiophene
  参考文献：
  名称：

  Synthesis, Structures, and Properties of Disubstituted Heteroacenes on One Side Containing Both Pyrrole and Thiophene Rings

  摘要：

  A new series of ladder-type heteroacenes containing both pyrrole and furan rings, 5,6-disubstituted diindolo[3,2-b:4,5-b']thiophenes (DITs), were effectively synthesized from N-functionalized 3,3'-dibromo-2,2'-biindoles undergoing intramolecular cyclization with bis(phenylsulfonyl) sulfide and organolithium. Single-crystal X-ray results demonstrate that 5,6-dipropyldiindolo[3,2-b:4,5-b']thiophene (4b) forms a herringbone-type of packing motif and 5,6-di(p-tolyl)diindolo[3,2-b:4,5-b']thiophene (4d) forms a parallel packing motif. Both of them have S-S contacts, enhancing the electronic transport between molecules. Their photophysical properties suggest that the skeleton of diindolo[3,2-b:4,5-b']thiophene is more favorable to aggregate in solid than that of indolo[3,2-b]carbazole. The large band gaps and low-lying HOMO energy levels could result in much better stability.

  DOI：

  10.1021/jo800622y