1-methyl-2,5-diphenyl-1H-imidazole 3-oxide | 1127563-25-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-methyl-2,5-diphenyl-1H-imidazole 3-oxide
• CAS: 1127563-25-0
• 化学式: C₁₆H₁₄N₂O
• 分子量: 250.3
• InChiKey: MOQTVJCOYYGIOF-UHFFFAOYSA-N

物化性质

• 熔点：
  198.5-199.2 °C
• 沸点：
  472.0±38.0 °C(predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  31.87
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-methyl-2,5-diphenyl-1H-imidazole 3-oxide 在 溶剂黄146 、 锌 作用下， 反应 1.5h， 以4.11 g的产率得到1-methyl-2,5-diphenylimidazole
  参考文献：
  名称：

  Cyclometalated Iridium(III) Complexes Based on Phenyl-Imidazole Ligand

  摘要：

  Phenyl-imidazole-based ligands with various substitution patterns have been used as the main ligand for heteroleptic bis-cyclometalated Iridium complexes. Two series of complexes have been prepared and their photophysical and electrochemical properties were studied. The phosphorescence emission maxima range from about 490 to 590 nm, that is, from greenish-blue to orange. The first series is of the form Ir(L)(2)(acac) (L: a phenyl-imidazole based ligand; acac: acetylacetonate). In the first complex, la, L is 1,4,5-trimethyl-2-phenyl-1H-imidazole. Then, methyl groups are replaced with phenyl groups and chlorines are grafted on the cyclometalated phenyl ring. The second series is of the form Ir(4,5-dimethyl-1,2-diphenyl-1H-imidazole)(2)(L-a) (L-a: ancillary ligand being acetylacetonate, acac, N,N-dimethylamir o-picolinate, NPic, picolinate, Pic, or 2-(diphenylphosphino)acetic acid, P). These series show that modifying the substitution pattern on the ligands can alter the photophysical and electrochemical properties of the complexes. Overall, we show that compared to complexes containing phenyl-pyridine ligands, highest occupied molecular orbitals (HOMOs) and lowest unoccupied molecular orbitals (LUMOs) are more delocalized over the entire main ligand in complexes containing phenyl-imidazole. Contrary to expectations, when chlorine atoms are used as strong acceptor substituents on the orthometalated phenyl, a red shift of the emission is observed. This behavior has been rationalized using theoretical calculations on the excited state of the chloro-substituted complex 3a compared to the model 1a.

  DOI：

  10.1021/ic901834v
• 作为产物：
  描述：

  溴苯 、 1-甲基-5-苯基-1H-咪唑3-氧化物 在 palladium diacetate 、 potassium carbonate 、 三(4-氟苯基)磷化氢 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以85%的产率得到1-methyl-2,5-diphenyl-1H-imidazole 3-oxide
  参考文献：
  名称：

  Campeau, Louis-Charles; Stuart, David R.; Leclerc, Jean-Philippe, Journal of the American Chemical Society, 2009, vol. 131, p. 3291 - 3306

  摘要：

  DOI：