9,9-diethyl-N2,N7-di(naphthalen-1-yl)-N2,N7-diphenyl-9H-fluorene-2,7-diamine | 143886-16-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 9,9-diethyl-N2,N7-di(naphthalen-1-yl)-N2,N7-diphenyl-9H-fluorene-2,7-diamine
• 英文别名: 2,7-bis(N-alpha-naphthyl-phenylamino)-9,9-diethylfluorene；9,9-diethyl-2-N,7-N-dinaphthalen-1-yl-2-N,7-N-diphenylfluorene-2,7-diamine
• CAS: 143886-16-2
• 化学式: C₄₉H₄₀N₂
• 分子量: 656.87
• InChiKey: QCJZLZPYJLEEQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.5
• 重原子数：
  51
• 可旋转键数：
  8
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9,9-diethyl-N2,N7-di(naphthalen-1-yl)-N2,N7-diphenyl-9H-fluorene-2,7-diamine 、 N-甲基甲酰苯胺 在 氯苯 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以44%的产率得到4-((9,9-diethyl-7-(naphthalen-1-yl(phenyl)amino)-9H-fluoren-2-yl)(naphthalen-1-yl)amino)benzaldehyde
  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

• Luminescent Ink Composition for Organic Electroluminescent Device
  申请人：Inoue Tetsuya

  公开号：US20080001123A1

  公开（公告）日：2008-01-03

  A luminescent ink composition for an organic EL device which can form thin films by a wet process easily due to a high solubility of a low-molecular material is provided in order to form an organic thin film containing a luminescent low-molecular material by a wet method with a high productivity. A luminescent ink composition for an organic electroluminescent device comprising: (A) an anthracene derivative represented by the following formula (1); (B) a condensed aromatic ring compound substituted with an arylamino group and/or a styryl derivative substituted with an arylamino group; and (C) an organic solvent.
• Ink For Forming Organic El Coating Film And Method For Production Thereof
  申请人：Inoue Tetsuya

  公开号：US20080093986A1

  公开（公告）日：2008-04-24

  An ink for forming an organic electroluminescent coating film capable of forming an emitting layer with a long life, which has a water concentration of 20 ppm or less and an oxygen concentration of 10 ppm or less wherein an aromatic compound, preferably an anthracene derivative, a pyrene derivative, and/or a fluorene derivative, is dissolved into an organic solvent, and a production method thereof are provided.
• US7229702B2
  申请人：——

  公开号：US7229702B2

  公开（公告）日：2007-06-12
• 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.