9,9'-(9,9-diethyl-9H-fluorene-2,7-diyl)bis(9H-carbazole) | 625371-06-4

• 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: 9,9'-(9,9-diethyl-9H-fluorene-2,7-diyl)bis(9H-carbazole)
• 英文别名: 9-(7-Carbazol-9-yl-9,9-diethylfluoren-2-yl)carbazole
• CAS: 625371-06-4
• 化学式: C₄₁H₃₂N₂
• 分子量: 552.718
• InChiKey: GIFYVTQZYDMSQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.7
• 重原子数：
  43
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  9.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  9,9'-(9,9-diethyl-9H-fluorene-2,7-diyl)bis(9H-carbazole) 在 ammonium acetate 、 氯苯 、 三氯氧磷 作用下， 以 溶剂黄146 为溶剂， 反应 28.0h， 生成 (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：

  咔唑 、 2,7-二溴-9,9-二乙基芴 在 copper(l) iodide 、 1,10-菲罗啉 、 potassium carbonate 作用下， 以 对二甲苯 为溶剂， 反应 48.0h， 以72%的产率得到9,9'-(9,9-diethyl-9H-fluorene-2,7-diyl)bis(9H-carbazole)
  参考文献：
  名称：

  Synthesis and Optoelectrochemical Properties of Stilbenophanes Having Carbazole Moieties

  摘要：

  A series of stilbenophanes having N-arylated carbazole moieties possessing small and large cavities have been synthesized via McMurry coupling of the corresponding dialdehyde derived from N-arylation of carbazole with various dibromide followed by formylation. The electrochemical, photophysical, and complexation properties of all the stilbenophanes with electron-deficient guest molecules like TCNQ, TCNE, and PQT were also carried out at different concentrations.

  DOI：

  10.1055/s-0032-1317324

文献信息

• LIGHT EMITTING POLYMER COMPOSITION AND POLYMER LIGHT EMITTING DEVICE
  申请人：Uetani Yasunori

  公开号：US20090039765A1

  公开（公告）日：2009-02-12

  A light emitting polymer composition comprising a light emitting polymer and a compound selected from the following formulae (1a) to (1d): (wherein, X represents an atom or atomic group forming a 5-membered or 6-membered ring together with four carbon atoms on two benzene rings in the formula, Q and T represent each independently a hydrogen atom, halogen atom, alkyl group, alkyloxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkyloxy group, arylalkylthio group, alkenyl group, alkynyl group, arylalkenyl group, arylalkynyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, substituted amino group, amide group, acid imide group, acyloxy group, mono-valent heterocyclic group, heteroaryloxy group, heteroarylthio group, cyano group or nitro group).

  一种发光聚合物组合物，包括一种发光聚合物和从以下公式（1a）至（1d）中选择的化合物：（其中，X代表与公式中两个苯环上的四个碳原子一起形成5元环或6元环的原子或原子团，Q和T分别独立地代表氢原子、卤素原子、烷基、烷氧基、烷硫基、芳基、芳氧基、芳硫基、芳基烷基、芳基烷氧基、芳基烷硫基、烯基、炔基、芳基烯基、芳基炔基、取代硅氧基、取代硅硫基、取代硅氨基、取代氨基、酰胺基、酸亚胺基、酰氧基、单价杂环基、杂芳氧基、杂芳硫基、氰基或硝基）。
• Synthesis and Optoelectrochemical Properties of Stilbenophanes Having Carbazole Moieties
  作者：Perumal Rajakumar、Karuppannan Sekar、Nagarathinam Venkatesan

  DOI：10.1055/s-0032-1317324

  日期：——

  A series of stilbenophanes having N-arylated carbazole moieties possessing small and large cavities have been synthesized via McMurry coupling of the corresponding dialdehyde derived from N-arylation of carbazole with various dibromide followed by formylation. The electrochemical, photophysical, and complexation properties of all the stilbenophanes with electron-deficient guest molecules like TCNQ, TCNE, and PQT were also carried out at different concentrations.
• 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.