4-(tridecan-7-yl)-4H-dithieno[3,2-b:2',3'-d]pyrrole-2-carbaldehyde | 1445739-56-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并噻吩类
• 英文名称: 4-(tridecan-7-yl)-4H-dithieno[3,2-b:2',3'-d]pyrrole-2-carbaldehyde
• CAS: 1445739-56-9
• 化学式: C₂₂H₃₁NOS₂
• 分子量: 389.626
• InChiKey: MGCJRRNXNYYZMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.21
• 重原子数：
  26.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  22.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(tridecan-7-yl)-4H-dithieno[3,2-b:2',3'-d]pyrrole-2-carbaldehyde 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以84%的产率得到6-Bromo-4-(tridecan-7-yl)-4H-dithieno[3,2-b:2',3'-d]pyrrole-2-carbaldehyde
  参考文献：
  名称：

  Unravelling the Potential for Dithienopyrrole Sensitizers in Dye-Sensitized Solar Cells

  摘要：

  Two D-pi-A dyes based on the dithieno[3,2-b:2',3'-d]pyrrole pi-bridge (DTP) were synthesized, characterized using UV-vis absorption spectroscopy and electrochemistry, modeled using quantum chemical calculations, and used as sensitizers in dye-sensitized solar cells (DSCs). The photoelectrochemical properties and DSC performance are thoroughly compared with their cyclopenta[1,2-b:5,4-b']dithiophene (CPDT) analogues. The use of DTP results in a small increase in the zero zero transition energy reflecting the higher lying lowest unoccupied molecular orbital that is commonly reported for DTP relative to CPDT systems. This increased optical gap manifests in slightly blue-shifted incident photon-to-collected electron conversion efficiency (IPCE) responses; however, increased open-circuit photovoltage values and improved charge-transfer kinetics relative to the CPDT systems result in comparable power conversion efficiencies. The present report highlights the potential of DTP for the development of tailored sensitizers employing stronger acceptors.

  DOI：

  10.1021/cm401144j
• 作为产物：
  描述：

  3,3'-二溴-2,2'-联噻吩 在 tris-(dibenzylideneacetone)dipalladium(0) 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 3.0h， 生成 4-(tridecan-7-yl)-4H-dithieno[3,2-b:2',3'-d]pyrrole-2-carbaldehyde
  参考文献：
  名称：

  Unravelling the Potential for Dithienopyrrole Sensitizers in Dye-Sensitized Solar Cells

  摘要：

  Two D-pi-A dyes based on the dithieno[3,2-b:2',3'-d]pyrrole pi-bridge (DTP) were synthesized, characterized using UV-vis absorption spectroscopy and electrochemistry, modeled using quantum chemical calculations, and used as sensitizers in dye-sensitized solar cells (DSCs). The photoelectrochemical properties and DSC performance are thoroughly compared with their cyclopenta[1,2-b:5,4-b']dithiophene (CPDT) analogues. The use of DTP results in a small increase in the zero zero transition energy reflecting the higher lying lowest unoccupied molecular orbital that is commonly reported for DTP relative to CPDT systems. This increased optical gap manifests in slightly blue-shifted incident photon-to-collected electron conversion efficiency (IPCE) responses; however, increased open-circuit photovoltage values and improved charge-transfer kinetics relative to the CPDT systems result in comparable power conversion efficiencies. The present report highlights the potential of DTP for the development of tailored sensitizers employing stronger acceptors.

  DOI：

  10.1021/cm401144j