9-(7-(9H-carbazol-9-yl)-9,9-diethyl-9H-fluoren-2-yl)-9H-carbazole-3-carbaldehyde | 1309350-80-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 9-(7-(9H-carbazol-9-yl)-9,9-diethyl-9H-fluoren-2-yl)-9H-carbazole-3-carbaldehyde
• 英文别名: 9-(7-Carbazol-9-yl-9,9-diethylfluoren-2-yl)carbazole-3-carbaldehyde
• CAS: 1309350-80-8
• 化学式: C₄₂H₃₂N₂O
• 分子量: 580.729
• InChiKey: UUUPAAPRYKYSAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  45
• 可旋转键数：
  5
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-(7-(9H-carbazol-9-yl)-9,9-diethyl-9H-fluoren-2-yl)-9H-carbazole-3-carbaldehyde 、 氰乙酸 在 ammonium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 12.0h， 以82%的产率得到(E)-3-(9-(7-(9H-carbazol-9-yl)-9,9-diethyl-9H-fluoren-2-yl)-9H-carbazol-3-yl)-2-cyanoacrylic acid
  参考文献：
  名称：

  2,7-Diaminofluorene-Based Organic Dyes for Dye-Sensitized Solar Cells: Effect of Auxiliary Donor on Optical and Electrochemical Properties

  摘要：

  New organic dyes containing a diarylaminofluorene unit as an electron donor and cyanoacrylic acid as acceptor and anchoring group in a donor-pi-donor-pi-acceptor architecture have been synthesized and characterized as sensitizers for nanocrystalline TiO2-based dye-sensitized solar cells. They have shown three major electronic absorptions originating from the pi-pi* and charge-transfer transitions covering the broad visible range (250-550 nm) in solution. The charge-transfer transition of the dyes exhibited negative solvatochromism, suggesting a polarized ground state. They have also displayed acidochromism in solution owing to the presence of a protonation-deprotonation equilibrium. On comparison with the triphenylamine and carbazole-based parent dyes (E)-2-cyano-3-(4-(diphenylamino)phenyl)acrylic acid and (E)-2-cyano-3-(9-ethyl-9H-carbazol-3-yl)acrylic acid they exhibited longer wavelength absorptions and facile oxidation, indicating the stronger electron-donating ability of the auxiliary chromophores. In addition, they exhibited nearly two times larger light-to-electron conversion efficiency under simulated AM 1.5 G irradiation (100 mW cm(-2)) with an aperture mask when compared to the parent dyes. Among the new dyes, the one containing the naphthylphenylamine segment showed better device characteristics attributable to the higher HOMO energy level which probably facilitates the regeneration of the dye and effective suppression of the back reaction of the injected electrons with the I-3(-) in the electrolyte. The optical properties of the dyes were modeled using TDDFT simulations employing different theoretical models (B3LYP, CAM-B3LYP, and MPW1K), and the best correlations with the observed parameters have been found for CAM-B3LYP and MPW1K calculations. The electron lifetimes extracted from the electrochemical impedance measurements of the dye-sensitized solar cells were used to interpret the solar cell efficiency alternations.

  DOI：

  10.1021/jo200501b
• 作为产物：
  描述：

  9,9'-(9,9-diethyl-9H-fluorene-2,7-diyl)bis(9H-carbazole) 、 N,N-二甲基甲酰胺 在 氯苯 、 三氯氧磷 作用下， 反应 16.0h， 以30%的产率得到9-(7-(9H-carbazol-9-yl)-9,9-diethyl-9H-fluoren-2-yl)-9H-carbazole-3-carbaldehyde
  参考文献：
  名称：

  2,7-Diaminofluorene-Based Organic Dyes for Dye-Sensitized Solar Cells: Effect of Auxiliary Donor on Optical and Electrochemical Properties

  摘要：

  New organic dyes containing a diarylaminofluorene unit as an electron donor and cyanoacrylic acid as acceptor and anchoring group in a donor-pi-donor-pi-acceptor architecture have been synthesized and characterized as sensitizers for nanocrystalline TiO2-based dye-sensitized solar cells. They have shown three major electronic absorptions originating from the pi-pi* and charge-transfer transitions covering the broad visible range (250-550 nm) in solution. The charge-transfer transition of the dyes exhibited negative solvatochromism, suggesting a polarized ground state. They have also displayed acidochromism in solution owing to the presence of a protonation-deprotonation equilibrium. On comparison with the triphenylamine and carbazole-based parent dyes (E)-2-cyano-3-(4-(diphenylamino)phenyl)acrylic acid and (E)-2-cyano-3-(9-ethyl-9H-carbazol-3-yl)acrylic acid they exhibited longer wavelength absorptions and facile oxidation, indicating the stronger electron-donating ability of the auxiliary chromophores. In addition, they exhibited nearly two times larger light-to-electron conversion efficiency under simulated AM 1.5 G irradiation (100 mW cm(-2)) with an aperture mask when compared to the parent dyes. Among the new dyes, the one containing the naphthylphenylamine segment showed better device characteristics attributable to the higher HOMO energy level which probably facilitates the regeneration of the dye and effective suppression of the back reaction of the injected electrons with the I-3(-) in the electrolyte. The optical properties of the dyes were modeled using TDDFT simulations employing different theoretical models (B3LYP, CAM-B3LYP, and MPW1K), and the best correlations with the observed parameters have been found for CAM-B3LYP and MPW1K calculations. The electron lifetimes extracted from the electrochemical impedance measurements of the dye-sensitized solar cells were used to interpret the solar cell efficiency alternations.

  DOI：

  10.1021/jo200501b

文献信息

• 2,7-Diaminofluorene-Based Organic Dyes for Dye-Sensitized Solar Cells: Effect of Auxiliary Donor on Optical and Electrochemical Properties
  作者：Abhishek Baheti、Prachi Singh、Chuan-Pei Lee、K. R. Justin Thomas、Kuo-Chuan Ho

  DOI：10.1021/jo200501b

  日期：2011.6.17

  New organic dyes containing a diarylaminofluorene unit as an electron donor and cyanoacrylic acid as acceptor and anchoring group in a donor-pi-donor-pi-acceptor architecture have been synthesized and characterized as sensitizers for nanocrystalline TiO2-based dye-sensitized solar cells. They have shown three major electronic absorptions originating from the pi-pi* and charge-transfer transitions covering the broad visible range (250-550 nm) in solution. The charge-transfer transition of the dyes exhibited negative solvatochromism, suggesting a polarized ground state. They have also displayed acidochromism in solution owing to the presence of a protonation-deprotonation equilibrium. On comparison with the triphenylamine and carbazole-based parent dyes (E)-2-cyano-3-(4-(diphenylamino)phenyl)acrylic acid and (E)-2-cyano-3-(9-ethyl-9H-carbazol-3-yl)acrylic acid they exhibited longer wavelength absorptions and facile oxidation, indicating the stronger electron-donating ability of the auxiliary chromophores. In addition, they exhibited nearly two times larger light-to-electron conversion efficiency under simulated AM 1.5 G irradiation (100 mW cm(-2)) with an aperture mask when compared to the parent dyes. Among the new dyes, the one containing the naphthylphenylamine segment showed better device characteristics attributable to the higher HOMO energy level which probably facilitates the regeneration of the dye and effective suppression of the back reaction of the injected electrons with the I-3(-) in the electrolyte. The optical properties of the dyes were modeled using TDDFT simulations employing different theoretical models (B3LYP, CAM-B3LYP, and MPW1K), and the best correlations with the observed parameters have been found for CAM-B3LYP and MPW1K calculations. The electron lifetimes extracted from the electrochemical impedance measurements of the dye-sensitized solar cells were used to interpret the solar cell efficiency alternations.