5-(8-(4-(4-(2,2-bis(2',4'-bis(hexyloxy)-[1,1'-biphenyl]-4-yl)vinyl)phenyl)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-7-yl)-2,3-diphenylquinoxalin-5-yl)thiophene-2-carbaldehyde | 1589533-93-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-(8-(4-(4-(2,2-bis(2',4'-bis(hexyloxy)-[1,1'-biphenyl]-4-yl)vinyl)phenyl)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-7-yl)-2,3-diphenylquinoxalin-5-yl)thiophene-2-carbaldehyde
• 英文别名: 5-[8-[4-[4-[2,2-bis[4-(2,4-dihexoxyphenyl)phenyl]ethenyl]phenyl]-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]indol-7-yl]-2,3-diphenylquinoxalin-5-yl]thiophene-2-carbaldehyde
• CAS: 1589533-93-6
• 化学式: C₉₂H₉₇N₃O₅S
• 分子量: 1356.87
• InChiKey: LIQUVLFZZPFHHU-UHFFFAOYSA-N

物化性质

• 密度：
  1.133±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  26.3
• 重原子数：
  101
• 可旋转键数：
  35
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-(8-(4-(4-(2,2-bis(2',4'-bis(hexyloxy)-[1,1'-biphenyl]-4-yl)vinyl)phenyl)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-7-yl)-2,3-diphenylquinoxalin-5-yl)thiophene-2-carbaldehyde 、 氰乙酸 在 ammonium acetate 、 溶剂黄146 作用下， 反应 12.0h， 以90%的产率得到(E)-3-(5-(8-(4-(4-(2,2-bis(2',4'-bis(hexyloxy)-[1,1'-biphenyl]-4-yl)vinyl)phenyl)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-7-yl)-2,3-diphenylquinoxalin-5-yl)thiophen-2-yl)-2-cyanoacrylic acid
  参考文献：
  名称：

  Influence of the Donor Size in D−π–A Organic Dyes for Dye-Sensitized Solar Cells

  摘要：

  We report two new molecularly engineered push-pull dyes, i.e., YA421 and YA422, based on substituted quinoxaline as a pi-conjugating linker and bulky-indoline moiety as donor and compared with reported IQ4 dye. Benefitting from increased steric hindrance with the introduction of bis(2,4-dihexyloxy)benzene substitution on the quinoxaline, the electron recombination between redox electrolyte and the TiO2 surface is reduced, especially in redox electrolyte employing Co(II/III) complexes as redox shuttles. It was found that the open circuit photovoltages of IQ4, YA421, and YA422 devices with cobalt-based electrolyte are higher than those with iodide/triiodide electrolyte by 34, 62, and 135 mV, respectively. Moreover, the cells employing graphene nanoplatelets on top of gold spattered film as a counter electrode (CE) show lower charge-transfer resistance compared to platinum as a CE. Consequently, YA422 devices deliver the best power conversion efficiency due to higher fill factor, reaching 10.65% at AM 1.5 simulated sunlight. Electrochemical impedance spectroscopy and transient absorption spectroscopy analysis were performed to understand the electrolyte influence on the device performances with different counter electrode materials and donor structures of donor-pi-acceptor dyes. Laser flash photolysis experiments indicate that even though the dye regeneration of YA422 is slower than that of the other two dyes, the slower back electron transfer of YA422 contributes to the higher device performance.

  DOI：

  10.1021/ja500280r
• 作为产物：
  描述：

  5-(8-bromo-2,3-diphenylquinoxalin-5-yl)thiophene-2-carbaldehyde 、 4-(4-(2,2-bis(2′,4′-bis(hexyloxy)-[1,1′-biphenyl]-4-yl)vinyl)phenyl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以75%的产率得到5-(8-(4-(4-(2,2-bis(2',4'-bis(hexyloxy)-[1,1'-biphenyl]-4-yl)vinyl)phenyl)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-7-yl)-2,3-diphenylquinoxalin-5-yl)thiophene-2-carbaldehyde
  参考文献：
  名称：

  Influence of the Donor Size in D−π–A Organic Dyes for Dye-Sensitized Solar Cells

  摘要：

  We report two new molecularly engineered push-pull dyes, i.e., YA421 and YA422, based on substituted quinoxaline as a pi-conjugating linker and bulky-indoline moiety as donor and compared with reported IQ4 dye. Benefitting from increased steric hindrance with the introduction of bis(2,4-dihexyloxy)benzene substitution on the quinoxaline, the electron recombination between redox electrolyte and the TiO2 surface is reduced, especially in redox electrolyte employing Co(II/III) complexes as redox shuttles. It was found that the open circuit photovoltages of IQ4, YA421, and YA422 devices with cobalt-based electrolyte are higher than those with iodide/triiodide electrolyte by 34, 62, and 135 mV, respectively. Moreover, the cells employing graphene nanoplatelets on top of gold spattered film as a counter electrode (CE) show lower charge-transfer resistance compared to platinum as a CE. Consequently, YA422 devices deliver the best power conversion efficiency due to higher fill factor, reaching 10.65% at AM 1.5 simulated sunlight. Electrochemical impedance spectroscopy and transient absorption spectroscopy analysis were performed to understand the electrolyte influence on the device performances with different counter electrode materials and donor structures of donor-pi-acceptor dyes. Laser flash photolysis experiments indicate that even though the dye regeneration of YA422 is slower than that of the other two dyes, the slower back electron transfer of YA422 contributes to the higher device performance.

  DOI：

  10.1021/ja500280r