4,5-dimethyl-1-(3,5-dimethylphenyl)-2-phenyl-1H-imidazole | 1262098-04-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,5-dimethyl-1-(3,5-dimethylphenyl)-2-phenyl-1H-imidazole
• 英文别名: dmdmppi；4,5-Dimethyl-1-(3,5-dimethylphenyl)-2-phenyl-1h-imidazole；1-(3,5-dimethylphenyl)-4,5-dimethyl-2-phenylimidazole
• CAS: 1262098-04-3
• 化学式: C₁₉H₂₀N₂
• 分子量: 276.381
• InChiKey: UQOMXZFHOFPUGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  氯化铱(III) 水合物 、 4,5-dimethyl-1-(3,5-dimethylphenyl)-2-phenyl-1H-imidazole 以 乙二醇乙醚 、 水 为溶剂， 生成 [IrCl((4,5-dimethyl-1-(3,5-dimethylphenyl)-2-phenyl-1H-imidazolato-N,C2)2]2
  参考文献：
  名称：

  Physicochemical studies of green phosphorescent light-emitting materials from cyclometalated heteroleptic iridium(III) complexes

  摘要：

  A series of novel imidazole ligands were synthesized and characterized. Phosphorescence studies of series of heteroleptic cyclometalated iridium(III) complexes reveal that these complexes possess dominantly (MLCT)-M-3 and (3)pi-pi* excited states and the solvent shifts of these complexes are interpreted by Richardt-Dimroth and Marcus solvent functions. The results consistent with prior assignments on the absorption band to a metal-to-ligand charge transfer excited state associated with chelating ligand. Emission kinetic studies exploited that the radiative transition (k(r)), increases with increasing lambda(em) and linear correlation exists between In(k(nr)) and energy gap. Electronic transition theory is applied to study the effect of E-g and Delta Q(e), on non-radiative transition (k(nr)). With a larger Delta Q(e), favouring vibrational overlap and leading to a larger value for k(nr). (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2011.02.052
• 作为产物：
  描述：

  苯甲醛 、 1-氨基-3,5-二甲苯 、 2,3-丁二酮 在 ammonium acetate 作用下， 以40%的产率得到4,5-dimethyl-1-(3,5-dimethylphenyl)-2-phenyl-1H-imidazole
  参考文献：
  名称：

  Synthesis, Structure, Luminescent and Intramolecular Proton Transfer in Some Imidazole Derivatives

  摘要：

  合成了一组新型2-芳基咪唑衍生物，并通过NMR谱、X射线、质量和CHN分析进行了表征。使用发射光谱研究了羟基咪唑（dmip 和 dmtip）中的激发态分子内质子转移（ESIPT）过程，并检测到 I 和 II 两种不同的基态旋转异构体分别负责正常和互变异构体发射。在烃溶剂中，对于 dmip 和 dmtip，互变异构体发射比正常发射占主导地位。这表明旋转异构体 II 负责互变异构体发射，并且它比导致正常发射的旋转异构体 I 更稳定。在乙醇等醇溶剂中，观察到正常发射的显着增强，这是由于溶剂化增加，极性更强的旋转异构体 I 变得比旋转异构体 II 更稳定。在二恶烷-水混合物中，观察到添加水会抑制 ESIPT 过程，因为涉及水的分子间氢键的形成。对咪唑衍生物的能量、偶极矩、基态和激发态旋转异构体的电荷分布进行了DFT计算并进行了讨论。 PES计算表明，激发态下两个旋转异构体相互转化的能垒比基态高。

  DOI：

  10.1007/s10895-010-0747-5

文献信息

• Synthesis, Structure, Luminescent and Intramolecular Proton Transfer in Some Imidazole Derivatives
  作者：Jayaraman Jayabharathi、Venugopal Thanikachalam、Natesan Srinivasan、Kanagarathinam Saravanan

  DOI：10.1007/s10895-010-0747-5

  日期：2011.3

  A group of novel 2-aryl imidazole derivatives were synthesized and characterized by NMR spectra, X-ray, mass and CHN analysis. An excited state intramolecular proton transfer (ESIPT) process in hydroxy imidazoles (dmip and dmtip) have been studied using emission spectroscopy and it was detected that the two distinct ground state rotamers of I and II are responsible for the normal and the tautomer emission respectively. In hydrocarbon solvent, the tautomer emission predominates over the normal emission for both dmip and dmtip. This reveal that rotamer II is responsible for the tautomer emission and it is stabler than rotamer I which causes the normal emission. In alcoholic solvent like ethanol, a dramatic enhancement of normal emission is observed which was due to increased solvation, the more polar rotamer I become stabler than rotamer II. In dioxane—water mixtures it is observed that the addition of water inhibits the ESIPT process due to the formation of the intermolecular hydrogen bonding involving water. DFT calculations on energy, dipole moment, charge distribution of the rotamers in the ground and excited states of the imidazole derivatives were performed and discussed. PES calculation indicates that the energy barrier for the interconversion of two rotamers is too high in the excited state than the ground state.

  合成了一组新型2-芳基咪唑衍生物，并通过NMR谱、X射线、质量和CHN分析进行了表征。使用发射光谱研究了羟基咪唑（dmip 和 dmtip）中的激发态分子内质子转移（ESIPT）过程，并检测到 I 和 II 两种不同的基态旋转异构体分别负责正常和互变异构体发射。在烃溶剂中，对于 dmip 和 dmtip，互变异构体发射比正常发射占主导地位。这表明旋转异构体 II 负责互变异构体发射，并且它比导致正常发射的旋转异构体 I 更稳定。在乙醇等醇溶剂中，观察到正常发射的显着增强，这是由于溶剂化增加，极性更强的旋转异构体 I 变得比旋转异构体 II 更稳定。在二恶烷-水混合物中，观察到添加水会抑制 ESIPT 过程，因为涉及水的分子间氢键的形成。对咪唑衍生物的能量、偶极矩、基态和激发态旋转异构体的电荷分布进行了DFT计算并进行了讨论。 PES计算表明，激发态下两个旋转异构体相互转化的能垒比基态高。
• Physicochemical studies of green phosphorescent light-emitting materials from cyclometalated heteroleptic iridium(III) complexes
  作者：Jayaraman Jayabharathi、Venugopal Thanikachalam、Natesan Srinivasan、Marimuthu Venkatesh Perumal

  DOI：10.1016/j.saa.2011.02.052

  日期：2011.7

  A series of novel imidazole ligands were synthesized and characterized. Phosphorescence studies of series of heteroleptic cyclometalated iridium(III) complexes reveal that these complexes possess dominantly (MLCT)-M-3 and (3)pi-pi* excited states and the solvent shifts of these complexes are interpreted by Richardt-Dimroth and Marcus solvent functions. The results consistent with prior assignments on the absorption band to a metal-to-ligand charge transfer excited state associated with chelating ligand. Emission kinetic studies exploited that the radiative transition (k(r)), increases with increasing lambda(em) and linear correlation exists between In(k(nr)) and energy gap. Electronic transition theory is applied to study the effect of E-g and Delta Q(e), on non-radiative transition (k(nr)). With a larger Delta Q(e), favouring vibrational overlap and leading to a larger value for k(nr). (C) 2011 Elsevier B.V. All rights reserved.