4-(2-(7-bromo-9-(4-(trifluoromethyl)phenyl)-9H-carbazol-2-yl)ethynyl)benzaldehyde | 1221683-76-6

• 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: 4-(2-(7-bromo-9-(4-(trifluoromethyl)phenyl)-9H-carbazol-2-yl)ethynyl)benzaldehyde
• 英文别名: 4-[2-[7-Bromo-9-[4-(trifluoromethyl)phenyl]carbazol-2-yl]ethynyl]benzaldehyde；4-[2-[7-bromo-9-[4-(trifluoromethyl)phenyl]carbazol-2-yl]ethynyl]benzaldehyde
• CAS: 1221683-76-6
• 化学式: C₂₈H₁₅BrF₃NO
• 分子量: 518.332
• InChiKey: IEBQWRJYYNYTAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-(7-bromo-9-(4-(trifluoromethyl)phenyl)-9H-carbazol-2-yl)ethynyl)benzaldehyde 、 3,6-di-tert-butyl-9-(4-ethynylphenyl)-9H-carbazole 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 反应 10.0h， 生成 4-(2-(7-(2-(4-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)ethynyl)-9-(4-(trifluoromethyl)phenyl)-9H-carbazol-2-yl)ethynyl)benzaldehyde
  参考文献：
  名称：

  咔唑供体-咔唑接头基化合物：制备，光物理性质和荧光纳米粒子的形成。

  摘要：

  一类新的高度可溶的和稳定的化合物（的1 - 4）已被合成和表征。化合物1，2，和3具有3,6-二取代的咔唑通过的2,7-位置处的电子供体-连接的N-取代的咔唑与可变取代苯基乙炔作为电子受体。化合物4有两个相同的供体通过N-取代的咔唑的2,7-位连接。这些化合物从紫外线吸收到可见光区域，并从蓝色强烈发射到绿色。已经研究了通过改变受体同时保持供体和连接体恒定对这些化合物的光物理性质的影响。对溶剂对其光物理性质的影响的研究表明，溶剂极性的增加会导致荧光量子产率的降低。随着温度的降低，这些化合物显示出增加的发射强度，伴随发射的红移。化合物2的边缘激发红移显示高达128 nm在异丙醇中。这些化合物的固态荧光量子产率从0.27到0.68不等。这些化合物的荧光寿命取决于溶剂。化合物2的发射随浓度显示出显着变化。化合物2和3在四氢呋喃/水混合物中形成高度稳定的荧光有机纳米粒子（FON）。通过Lipert-

  DOI：

  10.1021/jp912286u
• 作为产物：
  描述：

  2,7-二溴咔唑 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 4-(2-(7-bromo-9-(4-(trifluoromethyl)phenyl)-9H-carbazol-2-yl)ethynyl)benzaldehyde
  参考文献：
  名称：

  Carbazole donor and carbazole or bithiophene bridged sensitizers for dye-sensitized solar cells

  摘要：

  Three metal-free organic sensitizers consisting of carbazole as an electron donor, carbazole or bithiophene as the linker and cyanoacrylic acid as the electron acceptor and anchoring groups were designed and synthesized for use in dye-sensitized solar cells (DSSCs). The sensitizers were characterized by H-1 and C-13 NMR, MALDI-TOF (or HRMS), UV-Vis, photoluminescence, and electrochemistry. The HOMO and LUMO electron distributions of the sensitizers were calculated using density functional theory on a B3LYP level for geometry optimization. The photovoltaic performance of the sensitizers in operational liquid junction-based DSSCs under AM 1.5 G one-sun excitation (100 mW/cm(2)) indicate that the sensitizers are promising candidates for use in DSSCs. Sensitizers 1 and 2 produce a power conversion efficiency of 2.70% with a maximum IPCE of 75% at 450 nm, while sensitizer 3 has a power conversion efficiency of 2.23% with a maximum IPCE of 66% at 440 nm. The sensitizers thus exhibit excellent photon-to-current conversion efficiencies in the blue region of the spectrum and serve as candidates for further strategic optimization in tandem cells. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2011.08.001

文献信息

• Synthesis and computational studies of diphenylamine donor-carbazole linker-based donor–acceptor compounds
  作者：Krishna Panthi、Patrick Z. El-Khoury、Alexander N. Tarnovsky、Thomas H. Kinstle

  DOI：10.1016/j.tet.2010.10.050

  日期：2010.12

  The design, synthesis, and electronic spectra of a novel series of organic diphenylamine donor-carbazole linker-based donor-acceptor compounds are reported. The low-lying electronic transitions in these compounds are investigated using a combination of conventional steady-state absorption spectroscopy and tools of computational photochemistry. The electronic transitions were found to depend both on the nature of the acceptor moiety and the presence/absence of a carbazole linker, not affected by the presence of the trifluoromethlyphenyl group in all the reported DA compounds. (C) 2010 Elsevier Ltd. All rights reserved.
• Carbazole donor and carbazole or bithiophene bridged sensitizers for dye-sensitized solar cells
  作者：Anthony C. Onicha、Krishna Panthi、Thomas H. Kinstle、Felix N. Castellano

  DOI：10.1016/j.jphotochem.2011.08.001

  日期：2011.9

  Three metal-free organic sensitizers consisting of carbazole as an electron donor, carbazole or bithiophene as the linker and cyanoacrylic acid as the electron acceptor and anchoring groups were designed and synthesized for use in dye-sensitized solar cells (DSSCs). The sensitizers were characterized by H-1 and C-13 NMR, MALDI-TOF (or HRMS), UV-Vis, photoluminescence, and electrochemistry. The HOMO and LUMO electron distributions of the sensitizers were calculated using density functional theory on a B3LYP level for geometry optimization. The photovoltaic performance of the sensitizers in operational liquid junction-based DSSCs under AM 1.5 G one-sun excitation (100 mW/cm(2)) indicate that the sensitizers are promising candidates for use in DSSCs. Sensitizers 1 and 2 produce a power conversion efficiency of 2.70% with a maximum IPCE of 75% at 450 nm, while sensitizer 3 has a power conversion efficiency of 2.23% with a maximum IPCE of 66% at 440 nm. The sensitizers thus exhibit excellent photon-to-current conversion efficiencies in the blue region of the spectrum and serve as candidates for further strategic optimization in tandem cells. (C) 2011 Elsevier B.V. All rights reserved.
• Carbazole Donor−Carbazole Linker-Based Compounds: Preparation, Photophysical Properties, and Formation of Fluorescent Nanoparticles
  作者：Krishna Panthi、Ravi M. Adhikari、Thomas H. Kinstle

  DOI：10.1021/jp912286u

  日期：2010.4.8

  emission intensity accompanied by a red shift of emission. Edge excitation red shift showed as much as 128 nm for compound 2 in isopropanol. Solid-state fluorescence quantum yields vary from 0.27 to 0.68 for these compounds. The fluorescence lifetimes of these compounds are solvent dependent. Compound 2 showed remarkable change in emission with concentration. Compounds 2 and 3 form highly stable fluorescent

  一类新的高度可溶的和稳定的化合物（的1 - 4）已被合成和表征。化合物1，2，和3具有3,6-二取代的咔唑通过的2,7-位置处的电子供体-连接的N-取代的咔唑与可变取代苯基乙炔作为电子受体。化合物4有两个相同的供体通过N-取代的咔唑的2,7-位连接。这些化合物从紫外线吸收到可见光区域，并从蓝色强烈发射到绿色。已经研究了通过改变受体同时保持供体和连接体恒定对这些化合物的光物理性质的影响。对溶剂对其光物理性质的影响的研究表明，溶剂极性的增加会导致荧光量子产率的降低。随着温度的降低，这些化合物显示出增加的发射强度，伴随发射的红移。化合物2的边缘激发红移显示高达128 nm在异丙醇中。这些化合物的固态荧光量子产率从0.27到0.68不等。这些化合物的荧光寿命取决于溶剂。化合物2的发射随浓度显示出显着变化。化合物2和3在四氢呋喃/水混合物中形成高度稳定的荧光有机纳米粒子（FON）。通过Lipert-