N,N-bis(9,9-diethyl-9H-fluoren-2-yl)amine | 1225029-69-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N,N-bis(9,9-diethyl-9H-fluoren-2-yl)amine
• 英文别名: bis(9,9-diethyl-9H-fluoren-2-yl)amine；N-(9,9-diethylfluoren-2-yl)-9,9-diethylfluoren-2-amine
• CAS: 1225029-69-5
• 化学式: C₃₄H₃₅N
• 分子量: 457.659
• InChiKey: KWQZPKZTVOVTGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-bis(9,9-diethyl-9H-fluoren-2-yl)amine 在 bis-triphenylphosphine-palladium(II) chloride 、 1,1'-双(二苯基膦)二茂铁 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 sodium t-butanolate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 64.0h， 生成
  参考文献：
  名称：

  Organic dyes containing fluoreneamine donor and carbazole π-linker for dye-sensitized solar cells

  摘要：

  A series of new organic dyes containing fluoreneamine-based donor and carbazole pi-spacer are reported. These dyes displayed longer wavelength charge transfer absorption when compared to that of the corresponding phenylamine analogs. Fluoreneamine-based donors shifted the lowest unoccupied molecular orbital upwardly which is beneficial for the injection of electrons from the excited dye into the conduction band of TiO2 and lowered the oxidation potential of the dyes. The electronic perturbations caused by the fluorene unit have been confirmed by the density functional theoretical calculations. A device fabricated using a dye featuring difluorenylaminocarbazole donor and thiophene in the pi-spacer exhibited promising power conversion efficiency (6.4%). The interfacial electron transfer kinetics has been elucidated by electrochemical impedance spectroscopy which showed the beneficial role of difluorenylamine unit in suppressing the electron recombination. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2015.07.034
• 作为产物：
  描述：

  9,9-diethyl-9H-fluoren-2-amine 、 2-溴-9,9-二乙基芴 在 1,1'-双(二苯基膦)二茂铁 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以64%的产率得到N,N-bis(9,9-diethyl-9H-fluoren-2-yl)amine
  参考文献：
  名称：

  Organic dyes containing fluoreneamine donor and carbazole π-linker for dye-sensitized solar cells

  摘要：

  A series of new organic dyes containing fluoreneamine-based donor and carbazole pi-spacer are reported. These dyes displayed longer wavelength charge transfer absorption when compared to that of the corresponding phenylamine analogs. Fluoreneamine-based donors shifted the lowest unoccupied molecular orbital upwardly which is beneficial for the injection of electrons from the excited dye into the conduction band of TiO2 and lowered the oxidation potential of the dyes. The electronic perturbations caused by the fluorene unit have been confirmed by the density functional theoretical calculations. A device fabricated using a dye featuring difluorenylaminocarbazole donor and thiophene in the pi-spacer exhibited promising power conversion efficiency (6.4%). The interfacial electron transfer kinetics has been elucidated by electrochemical impedance spectroscopy which showed the beneficial role of difluorenylamine unit in suppressing the electron recombination. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2015.07.034

文献信息

• Dipolar Compounds Containing Fluorene and a Heteroaromatic Ring as the Conjugating Bridge for High-Performance Dye-Sensitized Solar Cells
  作者：Chih-Hsin Chen、Ying-Chan Hsu、Hsien-Hsin Chou、K. R. Justin Thomas、Jiann T. Lin、Chao-Ping Hsu

  DOI：10.1002/chem.200903151

  日期：2010.3.8

  A novel series of dipolar organic dyes containing diarylamine as the electron donor, 2‐cyanoacrylic acid as the electron acceptor, and fluorene and a heteroaromatic ring as the conjugating bridge have been developed and characterized. These metal‐free dyes exhibited very high molar extinction coefficients in the electronic absorption spectra and have been successfully fabricated as efficient nanocrystalline

  已经开发并表征了一系列新颖的偶极有机染料，其中包含二芳基胺作为电子供体，2-氰基丙烯酸作为电子受体，芴和杂芳环作为共轭桥。这些无金属的染料在电子吸收光谱中具有很高的摩尔消光系数，并已成功地制成了高效的纳米晶TiO 2染料敏化太阳能电池（DSSC）。DSSC的太阳能转换效率为4.92％至6.88％，达到了在相同条件下制造和测量的N719标准设备的68％至96％。含TiO 2膜厚为6μm，基于这些染料的DSSC的光电流超过了基于N719的设备的光电流。这些染料的DFT计算结果还提供了有关其高电池性能的详细结构信息。
• Synthesis, optical, electrochemical and photovoltaic properties of organic dyes containing trifluorenylamine donors
  作者：Abhishek Baheti、Satyanarayana Reddy Gajjela、Palani Balaya、K.R. Justin Thomas

  DOI：10.1016/j.dyepig.2014.07.036

  日期：2015.2

  loading data, incident photon to current conversion efficiency and the interfacial kinetic parameters estimated from the intensity modulated photovoltage/photocurrent spectral measurements. A dye with fluorene and bithiophene segments in the π-linker exhibited device efficiency up to 5.8%. The enhanced power conversion efficiency exhibited by this dye when compared to its analogue containing diphenylaminofluorne

  合成了两种新的基于三芴基胺供体和氰基丙烯酸受体的有机染料，并通过光学和电化学测量以及密度泛函理论计算对它们进行了表征。发现与三苯胺供体相比，三芴基胺供体有利于红移吸收并降低氧化电势。染料的光载量数据，入射光子到电流的转换效率以及根据强度调制的光电压/光电流光谱测量值估算的界面动力学参数，证实了染料在光伏性能方面的变化。在π-接头中具有芴和联噻吩链段的染料显示出高达5.8％的器件效率。