2-(anthracen-9-yl)-1-ethyl-1H-imidazo[4,5-f][1,10]phenanthroline | 1129868-45-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 2-(anthracen-9-yl)-1-ethyl-1H-imidazo[4,5-f][1,10]phenanthroline
• 英文别名: 2-(anthracen-9-yl)-1-ethyl-imidazo[4,5-f][1,10]phenanthroline；2-(9-anthryl)-1-ethyl-1H-imidazo[4,5-f][1,10]phenanthroline；acip；aeip；2-Anthracen-9-yl-3-ethylimidazo[4,5-f][1,10]phenanthroline
• CAS: 1129868-45-6
• 化学式: C₂₉H₂₀N₄
• 分子量: 424.505
• InChiKey: KWVUNMGOMPAVCB-UHFFFAOYSA-N

物化性质

• 沸点：
  728.9±63.0 °C(predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  五羰基氯铼(I) 、 2-(anthracen-9-yl)-1-ethyl-1H-imidazo[4,5-f][1,10]phenanthroline 以 甲苯 为溶剂， 以79%的产率得到Re(CO)3Cl(2-(anthracen-9-yl)-1-ethyl-imidazo[4,5-f][1,10]phenanthroline)
  参考文献：
  名称：

  基于 Re(CO)3Cl(aeip) 的可见光激发单线态氧发光探针

  摘要：

  一种新的铼 (I) 配合物 Re(CO)3Cl(aeip) [其中 aeip =2-(anthracen-9-yl)-1-ethyl-imidazo[4,5-f][1,10] 菲咯啉]，被设计和合成为在 410 nm 可见光激发下的发光探针，用于检测水介质中的单线态氧 (1O2)。新的复合物可以在中性和碱性介质中与 1O2 发生特异性反应，这导致显着的发光增强，发光量子产率分别增加了 8 倍和 18.7 倍。可见光激发可使复合物对生物系统有用。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  DOI：

  10.1002/ejic.200800699
• 作为产物：
  描述：

  2-(9-anthryl)-1H-imidazo[4,5-f][1,10]phenanthroline 、 溴乙烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以40%的产率得到2-(anthracen-9-yl)-1-ethyl-1H-imidazo[4,5-f][1,10]phenanthroline
  参考文献：
  名称：

  基于 Re(CO)3Cl(aeip) 的可见光激发单线态氧发光探针

  摘要：

  一种新的铼 (I) 配合物 Re(CO)3Cl(aeip) [其中 aeip =2-(anthracen-9-yl)-1-ethyl-imidazo[4,5-f][1,10] 菲咯啉]，被设计和合成为在 410 nm 可见光激发下的发光探针，用于检测水介质中的单线态氧 (1O2)。新的复合物可以在中性和碱性介质中与 1O2 发生特异性反应，这导致显着的发光增强，发光量子产率分别增加了 8 倍和 18.7 倍。可见光激发可使复合物对生物系统有用。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  DOI：

  10.1002/ejic.200800699

文献信息

• A Series of Cu ^I Complexes Containing 1,10‐Phenanthroline Derivative Ligands: Synthesis, Characterization, Photophysical, and Oxygen‐Sensing Properties
  作者：Linfang Shi、Bin Li

  DOI：10.1002/ejic.200900123

  日期：2009.5

  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)
• DNA groove-binding and acid-base properties of a Ru(II) complex containing anthryl moieties
  作者：Hong-Ju Yin、An-Guo Zhang、Li-Hua Gao、Hua Zhao、Ke-Zhi Wang

  DOI：10.1080/15257770.2019.1669804

  日期：2020.4.2

  DNA groove binders have been poorly studied as compared to the intercalators. A novel Ru(II) complex of [Ru(aeip)(2)(Haip)](PF6)(2) Haip = 2-(9-anthryl)-1H-imidazo[4,5-f][1,10]phenanthroline and aeip = 2-(anthracen-9-yl)-1-ethylimidazo[4,5-f][1, 10]phenanthroline} is synthesized and characterized by elemental analysis, H-1 NMR spectroscopy and mass spectrometry. The complex is evidenced to be a calf-thymus DNA groove binder with a large intrinsic binding constant of 10(6) M-1 order of magnitude as supported by UV-visible absorption spectral titrations, salt effects, DNA competitive binding with ethidium bromide, DNA melting experiment, DNA viscosity measurements and density functional theory calculations. The acid-base properties of the complex studied by UV-Vis spectrophotometric titrations are reported as well.