4-(4-(hexyloxy)phenyl)-6-iodo-4H-dithieno[3,2-b:2',3'-d]pyrrole-2-carbaldehyde | 1572185-76-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-(4-(hexyloxy)phenyl)-6-iodo-4H-dithieno[3,2-b:2',3'-d]pyrrole-2-carbaldehyde
• 英文别名: 7-(4-Hexoxyphenyl)-10-iodo-3,11-dithia-7-azatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene-4-carbaldehyde
• CAS: 1572185-76-2
• 化学式: C₂₁H₂₀INO₂S₂
• 分子量: 509.432
• InChiKey: HWNIEKLZDWJNAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  87.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-(hexyloxy)phenyl)-6-iodo-4H-dithieno[3,2-b:2',3'-d]pyrrole-2-carbaldehyde 在 哌啶 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 氯仿 、 乙腈 为溶剂， 生成 2-cyano-3-(6-(4-(diphenylamino)phenyl)-4-(4-(hexyloxy)phenyl)-4H-dithieno[3,2-b:2',3'-d]pyrrol-2-yl)acrylic acid
  参考文献：
  名称：

  N-Alkyl- and N-aryl-dithieno[3,2-b:2′,3′-d]pyrrole-containing organic dyes for efficient dye-sensitized solar cells

  摘要：

  Two new organic sensitizers, 2-cyano-3-(6-(4-(diphenylamino)phenyl)-4-(2-ethylhexyl)-4H-dithieno 13,2-b:2',3'-d]pyrrol-2-yl)acrylic acid and 2-cyano-3-(6-(4-(diphenylamino)phenyl)-4-(4-(hexyloxy) phenyl)-4H-dithieno[3,2-b:2',3'-d]pyrrol-2-yl)acrylic acid, consisting of electron donating (triphenylamine) and electron accepting (cyanoacrylic acid) functionalities linked by two different rigidified pi-spacers, N-alkyl- and N-aryl-dithieno[3,2-b:2',3'-d]pyrrole, were designed, synthesized and applied for dye-sensitized solar cells, respectively. The materials were successfully synthesized through Knoevenagel condensation reactions. Ultraviolet-visible absorption spectra revealed that the use of either of rigidified pi-spacer resulted in similar charge transfer transition, however, enhanced spectral response was observed when compared with an oligothiophene analogue. In terms of their photovoltaic performance, new dyes outperformed the reference bithiophene sensitizer when tested with nitrile-based and ionic liquid-based electrolytes. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.02.002
• 作为产物：
  描述：

  N-(4-(hexyloxy)phenyl)-dithieno[3,2-b:2',3'-d]pyrrole 在 N-碘代丁二酰亚胺 、 溶剂黄146 、 三氯氧磷 作用下， 以 氯仿 、 1,2-二氯乙烷 为溶剂， 生成 4-(4-(hexyloxy)phenyl)-6-iodo-4H-dithieno[3,2-b:2',3'-d]pyrrole-2-carbaldehyde
  参考文献：
  名称：

  N-Alkyl- and N-aryl-dithieno[3,2-b:2′,3′-d]pyrrole-containing organic dyes for efficient dye-sensitized solar cells

  摘要：

  Two new organic sensitizers, 2-cyano-3-(6-(4-(diphenylamino)phenyl)-4-(2-ethylhexyl)-4H-dithieno 13,2-b:2',3'-d]pyrrol-2-yl)acrylic acid and 2-cyano-3-(6-(4-(diphenylamino)phenyl)-4-(4-(hexyloxy) phenyl)-4H-dithieno[3,2-b:2',3'-d]pyrrol-2-yl)acrylic acid, consisting of electron donating (triphenylamine) and electron accepting (cyanoacrylic acid) functionalities linked by two different rigidified pi-spacers, N-alkyl- and N-aryl-dithieno[3,2-b:2',3'-d]pyrrole, were designed, synthesized and applied for dye-sensitized solar cells, respectively. The materials were successfully synthesized through Knoevenagel condensation reactions. Ultraviolet-visible absorption spectra revealed that the use of either of rigidified pi-spacer resulted in similar charge transfer transition, however, enhanced spectral response was observed when compared with an oligothiophene analogue. In terms of their photovoltaic performance, new dyes outperformed the reference bithiophene sensitizer when tested with nitrile-based and ionic liquid-based electrolytes. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.02.002