2-(2,4-difluorophenyl)-1-phenyl-1H-imidazo[4,5-f][1,10]phenanthroline | 1350748-77-4

• 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-(2,4-difluorophenyl)-1-phenyl-1H-imidazo[4,5-f][1,10]phenanthroline
• 英文别名: 2-(2,4-Difluorophenyl)-3-phenylimidazo[4,5-f][1,10]phenanthroline；2-(2,4-difluorophenyl)-3-phenylimidazo[4,5-f][1,10]phenanthroline
• CAS: 1350748-77-4
• 化学式: C₂₅H₁₄F₂N₄
• 分子量: 408.41
• InChiKey: WMJOCBVHINBBPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  六氟磷酸钾 、 [iridium(III)(μ-chloro)(2-phenylpyridine)2]2 、 2-(2,4-difluorophenyl)-1-phenyl-1H-imidazo[4,5-f][1,10]phenanthroline 以 乙醇 、 二氯甲烷 为溶剂， 反应 10.0h， 以65%的产率得到
  参考文献：
  名称：

  Tuning Photophysical and Electrochemical Properties of Phosphorescent Heteroleptic Iridium Complex Salts–as Chemosensors

  摘要：

  对环甲基化阳离子杂环铱（III）复盐进行了光物理和电化学研究。这些复盐在 263 nm 附近出现了强烈的吸收带，这些吸收带属于菲罗啉配体的自旋允许的 π-π* 转变。在 341 和 440 nm 附近分别观察到中等强度和较弱的吸收带。这些吸收带分别是自旋允许的金属到配体电荷转移 1MLCT 和 3MLCT 过渡。此外，还研究了阴离子和质子对光物理和电化学研究的影响。加入 CF3CO2H 后，发射波长发生红移，发射颜色由黄色变为红色。加入 F-、CH3COO- 和 H2PO4 - 等阴离子后，溶液颜色由绿色变为棕色，发射被淬灭。

  DOI：

  10.1007/s10895-013-1310-y
• 作为产物：
  描述：

  1,10-邻二氮杂菲-5,6-二酮 、 2,4-二氟苯甲醛 、 苯胺 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 以60%的产率得到2-(2,4-difluorophenyl)-1-phenyl-1H-imidazo[4,5-f][1,10]phenanthroline
  参考文献：
  名称：

  Physicochemical and solvatochromic analysis of an imidazole derivative as NLO material

  摘要：

  Bioactive imidazole derivative, 2-(2,4-difluorophenyl)-1-phenyl-1H-imidazo[4,5-f][1,10]phenanthroline, has been synthesized and characterized by IR, UV-vis, NMR and elemental (CHN) analysis. The electric dipole moment (μ) and the hyperpolarizability (β) have been studied both experimentally and theoretically, which reveals that the synthesized imidazole derivative possesses non-linear optical (NLO) behavior. This chromophore possess more appropriate ratio of off-diagonal versus diagonal β tensorial component (r=β(xyy)/β(xxx)=-0.19) which reflects the in plane nonlinearity anisotropy. Since they have largest μβ(0) value, the reported imidazole can be used as potential NLO material. Within this context, reasonable conclusions concerning the steric hindrance in the chromospheres, push-pull character, hyperpolarizability of the imidazole and their application as NLO materials will be drawn. The solvent effect on the absorption and fluorescence bands was analyzed by a multi-component linear regression in which several solvent parameters were analyzed simultaneously.

  DOI：

  10.1016/j.saa.2011.08.060

文献信息

• Physicochemical and solvatochromic analysis of an imidazole derivative as NLO material
  作者：Jayaraman Jayabharathi、Venugopal Thanikachalam、Marimuthu Venkatesh Perumal

  DOI：10.1016/j.saa.2011.08.060

  日期：2012.1

  Bioactive imidazole derivative, 2-(2,4-difluorophenyl)-1-phenyl-1H-imidazo[4,5-f][1,10]phenanthroline, has been synthesized and characterized by IR, UV-vis, NMR and elemental (CHN) analysis. The electric dipole moment (μ) and the hyperpolarizability (β) have been studied both experimentally and theoretically, which reveals that the synthesized imidazole derivative possesses non-linear optical (NLO) behavior. This chromophore possess more appropriate ratio of off-diagonal versus diagonal β tensorial component (r=β(xyy)/β(xxx)=-0.19) which reflects the in plane nonlinearity anisotropy. Since they have largest μβ(0) value, the reported imidazole can be used as potential NLO material. Within this context, reasonable conclusions concerning the steric hindrance in the chromospheres, push-pull character, hyperpolarizability of the imidazole and their application as NLO materials will be drawn. The solvent effect on the absorption and fluorescence bands was analyzed by a multi-component linear regression in which several solvent parameters were analyzed simultaneously.
• Tuning Photophysical and Electrochemical Properties of Phosphorescent Heteroleptic Iridium Complex Salts–as Chemosensors
  作者：J. Jayabharathi、R. Sathishkumar、V. Thanikachalam、K. Jayamoorthy

  DOI：10.1007/s10895-013-1310-y

  日期：2014.3

  Photophysical and electrochemical studies of cyclometalated cationic heteroleptic iridium(III) complex salts have been carried out. For these complex salts the intense absorption bands appeared around 263 nm and are assigned to spin-allowed π-π* transitions of phenanthroline ligands. Moderately intense and weak absorption bands observed around 341 and 440 nm, respectively. These bands are assigned to spin-allowed metal to ligand charge transfer 1MLCT and 3MLCT transitions, respectively. The influence of anions and proton on the photophysical and electrochemical studies were also carried out. The emission wavelength was red shifted and emission color changed from yellow to red by the addition of CF3CO2H. The solution color changed from green to brown and the emission was quenched by the addition anions such as of F−, CH3COO− and H2PO4 −.

  对环甲基化阳离子杂环铱（III）复盐进行了光物理和电化学研究。这些复盐在 263 nm 附近出现了强烈的吸收带，这些吸收带属于菲罗啉配体的自旋允许的 π-π* 转变。在 341 和 440 nm 附近分别观察到中等强度和较弱的吸收带。这些吸收带分别是自旋允许的金属到配体电荷转移 1MLCT 和 3MLCT 过渡。此外，还研究了阴离子和质子对光物理和电化学研究的影响。加入 CF3CO2H 后，发射波长发生红移，发射颜色由黄色变为红色。加入 F-、CH3COO- 和 H2PO4 - 等阴离子后，溶液颜色由绿色变为棕色，发射被淬灭。