6-(4-(diphenylamino)phenyl)-4-(4-(hexyloxy)phenyl)-4H-dithieno[3,2-b:2',3'-d]pyrrole-2-carbaldehyde | 1572185-77-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 6-(4-(diphenylamino)phenyl)-4-(4-(hexyloxy)phenyl)-4H-dithieno[3,2-b:2',3'-d]pyrrole-2-carbaldehyde
• 英文别名: 7-(4-hexoxyphenyl)-10-[4-(N-phenylanilino)phenyl]-3,11-dithia-7-azatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene-4-carbaldehyde
• CAS: 1572185-77-3
• 化学式: C₃₉H₃₄N₂O₂S₂
• 分子量: 626.843
• InChiKey: OOQLDDUOGJBYLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  91
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(4-(diphenylamino)phenyl)-4-(4-(hexyloxy)phenyl)-4H-dithieno[3,2-b:2',3'-d]pyrrole-2-carbaldehyde 、 氰乙酸 在 哌啶 作用下， 以 氯仿 、 乙腈 为溶剂， 以34%的产率得到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：

  3,3'-二溴-2,2'-联噻吩 在 1,1'-双(二苯基膦)二茂铁 、 N-碘代丁二酰亚胺 、 四(三苯基膦)钯 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium tert-butylate 、 potassium carbonate 、 溶剂黄146 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 氯仿 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 0.25h， 生成 6-(4-(diphenylamino)phenyl)-4-(4-(hexyloxy)phenyl)-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

文献信息

• N-Alkyl- and N-aryl-dithieno[3,2-b:2′,3′-d]pyrrole-containing organic dyes for efficient dye-sensitized solar cells
  作者：Akhil Gupta、Melissa M.A. Kelson、Vanessa Armel、Ante Bilic、Sheshanath V. Bhosale

  DOI：10.1016/j.tet.2014.02.002

  日期：2014.3

  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.