1-ethyl-2-phenyl-1H-imidazo[4,5-f][1,10]phenanthroline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-ethyl-2-phenyl-1H-imidazo[4,5-f][1,10]phenanthroline
• 英文别名: 1-ethyl-2-phenylimidazo[4,5-f][1,10]-phenanthroline；1-ethyl-2-phenylimidazo[4,5-f][1,10]phenanthroline；epip；3-ethyl-2-phenylimidazo[4,5-f]-1,10-phenanthroline；3-Ethyl-2-phenylimidazo[4,5-f][1,10]phenanthroline
• 化学式: C₂₁H₁₆N₄
• 分子量: 324.385
• InChiKey: QBCBUOOAOWEHDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-ethyl-2-phenyl-1H-imidazo[4,5-f][1,10]phenanthroline 、 tetrakis(acetonitrile)copper(I)tetrafluoroborate 、 双(2-二苯基磷苯基)醚 以 二氯甲烷 为溶剂， 以73%的产率得到[(dpephos)(1-ethyl-2-phenyl-1H-imidazo[4,5-f][1,10]phenanthroline)copper(I)]BF4
  参考文献：
  名称：

  A Series of Cu ^I Complexes Containing 1,10‐Phenanthroline Derivative Ligands: Synthesis, Characterization, Photophysical, and Oxygen‐Sensing Properties

  摘要：

  AbstractFive novel copper(I) complexes with the general formula [Cu(dpephos)(NN)]BF4 {dpephos = bis[2‐(diphenylphosphanyl)phenyl] ether, NN = 2‐phenyl‐1H‐imidazo[4,5‐f][1,10]phenanthroline (pip, 1), 1‐ethyl‐2‐phenyl‐1H‐imidazo[4,5‐f][1,10]phenanthroline (epip, 2), 2‐(naphthalen‐1‐yl)‐1H‐imidazo[4,5‐f][1,10]phenanthroline (nip, 3), 1‐ethyl‐2‐(naphthalen‐1‐yl)‐1H‐imidazo[4,5‐f][1,10]phenanthroline (enip, 4), 2‐(anthracen‐9‐yl)‐1‐ethyl‐1H‐imidazo[4,5‐f][1,10]phenanthroline (aeip, 5)} were rationally designed and synthesized, and these complexes were characterized by 1H NMR and IR spectroscopy and elemental analysis. X‐ray crystal‐structure analysis of 3 and 4 are also presented. Their photophysical properties at room temperature were examined by using a combination of cyclic voltammetry and electronic absorption spectroscopy. It was found that 1–4 display broad‐band emission in the solid state upon excitation at λ = 400 nm, and the emission maxima are located in the range 530–558 nm; the excited‐state lifetimes of these complexes are 8.24, 1.97, 6.99, and 2.43 μs, respectively. As a result, the emission intensity of complexes 1–4 is sensitive to oxygen concentration, and they display oxygen‐sensing properties after they are encapsulated into mesoporous silica MCM‐41 or SBA‐15.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejic.200900123
• 作为产物：
  描述：

  溴乙烷 、 2-phenyl-1H-imidazo[4,5-f ][1,10]phenanthroline 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 以72%的产率得到1-ethyl-2-phenyl-1H-imidazo[4,5-f][1,10]phenanthroline
  参考文献：
  名称：

  A Series of Cu ^I Complexes Containing 1,10‐Phenanthroline Derivative Ligands: Synthesis, Characterization, Photophysical, and Oxygen‐Sensing Properties

  摘要：

  AbstractFive novel copper(I) complexes with the general formula [Cu(dpephos)(NN)]BF4 {dpephos = bis[2‐(diphenylphosphanyl)phenyl] ether, NN = 2‐phenyl‐1H‐imidazo[4,5‐f][1,10]phenanthroline (pip, 1), 1‐ethyl‐2‐phenyl‐1H‐imidazo[4,5‐f][1,10]phenanthroline (epip, 2), 2‐(naphthalen‐1‐yl)‐1H‐imidazo[4,5‐f][1,10]phenanthroline (nip, 3), 1‐ethyl‐2‐(naphthalen‐1‐yl)‐1H‐imidazo[4,5‐f][1,10]phenanthroline (enip, 4), 2‐(anthracen‐9‐yl)‐1‐ethyl‐1H‐imidazo[4,5‐f][1,10]phenanthroline (aeip, 5)} were rationally designed and synthesized, and these complexes were characterized by 1H NMR and IR spectroscopy and elemental analysis. X‐ray crystal‐structure analysis of 3 and 4 are also presented. Their photophysical properties at room temperature were examined by using a combination of cyclic voltammetry and electronic absorption spectroscopy. It was found that 1–4 display broad‐band emission in the solid state upon excitation at λ = 400 nm, and the emission maxima are located in the range 530–558 nm; the excited‐state lifetimes of these complexes are 8.24, 1.97, 6.99, and 2.43 μs, respectively. As a result, the emission intensity of complexes 1–4 is sensitive to oxygen concentration, and they display oxygen‐sensing properties after they are encapsulated into mesoporous silica MCM‐41 or SBA‐15.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejic.200900123

文献信息

• WO2007/6026
  申请人：——

  公开号：——

  公开（公告）日：——
• A new carbazole-based phenanthrenyl ruthenium complex as sensitizer for a dye-sensitized solar cell
  作者：Xianghong Li、John Gui、Hong Yang、Wenjun Wu、Fuyou Li、He Tian、Chunhui Huang

  DOI：10.1016/j.ica.2008.02.027

  日期：2008.6

  Three new amphiphilic ruthenium complexes (Ru-1, Ru-2 and Ru-3) based on phenanthrenyl derivatives have been synthesized and used as photosensitizers for dye-sensitized solar cells (DSSCs). The ruthenium complex Ru-1 containing a carbazole group showed especially improved photophysical properties (red-shifted metal-to-ligand charge-transfer transition absorptions and enhanced molar extinction coefficients)and interesting electrochemical properties, resulting in its improved open circuit potential and high overall light-to-electric power conversion efficiency of 5.3% (AM1.5,75 mW/cm(2)). These facts indicate that the carbazole-based phenanthrenyl ruthenium complex is a promising candidate for improving the conversion efficiency of dye-sensitized solar cells. (c) 2008 Elsevier B.V. All rights reserved.
• Tuning Photophysical and Electrochemical Properties of Cationic Iridium(III) Complex Salts with Imidazolyl Substituents by Proton and Anions
  作者：Qiang Zhao、Shujuan Liu、Mei Shi、Fuyou Li、Hao Jing、Tao Yi、Chunhui Huang

  DOI：10.1021/om700623j

  日期：2007.11.1

  A series of cationic iridium(III) complex salts, 1-5, were synthesized containing different phenanthroline derivatives. Their photophysical and electrochemical properties were investigated. The influences of anions and proton on the photophysical and electrochemical properties were also studied in detail. Upon addition of CF3COOH, the emission wavelength was significantly red-shifted and the emission color changed from yellow to red. In addition, the addition of F-, CH3COO-, and H2PO4- can also cause significant variations in UV-vis absorption and emission spectra. Upon addition of F-, CH3COO-, and H2PO4-, the solution colors of 1-3 changed from yellow-green to brown and the emission of 1-3 was quenched completely, which can be observed by the naked eye.
• Compositions and use thereof in dye sensitized solar cells
  申请人：Gui Yupeng John

  公开号：US20070000539A1

  公开（公告）日：2007-01-04

  The present invention provides in one aspect a composition having at least one metal complex, such that the metal complex comprises at least one metal atom, a phenanthroline-based first ligand and a second ligand comprising at least one acidic group, and at least two coordinative nitrogen atoms capable of simultaneous binding to the metal atom. This composition may be disposed on a semiconductor layer which is further disposed on an electrically conductive surface to provide a dye-sensitized electrode. The dye-sensitized electrode can be assembled together with a counter electrode and a redox electrolyte to provide a dye-sensitized solar cell.
• [EN] COMPOSITIONS AND USE THEREOF IN DYE SENSITIZED SOLAR CELLS<br/>[FR] COMPOSITIONS ET UTILISATION DE CELLES-CI DANS DES PILES SOLAIRES A COLORANT
  申请人：GEN ELECTRIC

  公开号：WO2007006026A1

  公开（公告）日：2007-01-11

  [EN] The present invention provides in one aspect a composition having at least one metal complex, such that the metal complex comprises at least one metal atom, a phenanthroline-based first ligand and a second ligand comprising at least one acidic group, and at least two coordinative nitrogen atoms capable of simultaneous binding to the metal atom. This composition may be disposed on a semiconductor layer which is further disposed on an electrically conductive surface to provide a dye- sensitized electrode. The dye-sensitized electrode can be assembled together with a counter electrode and a redox electrolyte to provide a dye-sensitized solar cell.
  [FR] La présente invention concerne une composition comprenant au moins un complexe métallique qui présente au moins un atome métallique, un premier ligand à base de phénanthroline et un second ligand comprenant au moins un groupe acide, ainsi qu'au moins deux atomes d'azote coordinatifs capables de se lier simultanément à l'atome métallique. Cette composition peut être placée sur une couche de semi-conducteur qui est ensuite placée sur une surface électroconductrice afin d'obtenir une électrode à colorant. Cette électrode à colorant peut alors être montée avec une contre-électrode et un électrolyte redox, afin d'obtenir une pile solaire à colorant.