2-(4-fluorophenyl)-1-(4-methoxyphenyl)-1H-imidazo[4,5-f][1,10]phenanthroline | 1374019-24-5

• 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: 2-(4-fluorophenyl)-1-(4-methoxyphenyl)-1H-imidazo[4,5-f][1,10]phenanthroline
• 英文别名: 2-(4-Fluorophenyl)-3-(4-methoxyphenyl)imidazo[4,5-f][1,10]phenanthroline；2-(4-fluorophenyl)-3-(4-methoxyphenyl)imidazo[4,5-f][1,10]phenanthroline
• CAS: 1374019-24-5
• 化学式: C₂₆H₁₇FN₄O
• 分子量: 420.446
• InChiKey: HBQBQCLQEAICFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  52.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,10-邻二氮杂菲-5,6-二酮 、 对氟苯甲醛 、 甲氧苯胺 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 168.0h， 以55%的产率得到2-(4-fluorophenyl)-1-(4-methoxyphenyl)-1H-imidazo[4,5-f][1,10]phenanthroline
  参考文献：
  名称：

  Photophysical studies of fused phenanthrimidazole derivatives as versatile π-conjugated systems for potential NLO applications

  摘要：

  Two new heterocyclic imidazole derivatives consists of pi-conjugated system attached to a phenanthrimidazole moiety have been synthesized in moderate yield by the condensation of 1,10-phenanthroline-5,6-dione with substituted aromatic aldehydes and 4-methoxyaniline in the presence of ammonium acetate in ethanol medium. The photophysical properties of these imidazole derivatives were studied in several solvents. These derivatives were evaluated concerning their solvatochromic properties and molecular optical nonlinearities. Their electric dipole moment (mu) and hyperpolarizability (beta) have been calculated theoretically and the results indicate that the extension of the pi-framework of the ligands has an effect on the NLO properties of these imidazole derivatives. The non-zero tensor components of these imidazole derivatives reveal that they possess potent non-linear optical (NLO) behavior. The energies of the HOMO and LUMO levels and the molecular electrostatic potential (MEP) energy surface studies have exploited the existence of intramolecular charge transfer (ICT) within the molecule. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2012.01.066

文献信息

• Photophysical studies of fused phenanthrimidazole derivatives as versatile π-conjugated systems for potential NLO applications
  作者：Jayaraman Jayabharathi、Venugopal Thanikachalam、Marimuthu Venkatesh Perumal

  DOI：10.1016/j.saa.2012.01.066

  日期：2012.6

  Two new heterocyclic imidazole derivatives consists of pi-conjugated system attached to a phenanthrimidazole moiety have been synthesized in moderate yield by the condensation of 1,10-phenanthroline-5,6-dione with substituted aromatic aldehydes and 4-methoxyaniline in the presence of ammonium acetate in ethanol medium. The photophysical properties of these imidazole derivatives were studied in several solvents. These derivatives were evaluated concerning their solvatochromic properties and molecular optical nonlinearities. Their electric dipole moment (mu) and hyperpolarizability (beta) have been calculated theoretically and the results indicate that the extension of the pi-framework of the ligands has an effect on the NLO properties of these imidazole derivatives. The non-zero tensor components of these imidazole derivatives reveal that they possess potent non-linear optical (NLO) behavior. The energies of the HOMO and LUMO levels and the molecular electrostatic potential (MEP) energy surface studies have exploited the existence of intramolecular charge transfer (ICT) within the molecule. (C) 2012 Elsevier B.V. All rights reserved.