2-(4-fluorophenyl)-4,5-dimethyl-1-p-tolyl-1H-imidazole | 1275593-77-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-fluorophenyl)-4,5-dimethyl-1-p-tolyl-1H-imidazole
• 英文别名: 4,5-dimethyl-1-(p-tolyl)-2-(4-fluorophenyl)-1H-imidazole；fpdmti；2-(4-Fluorophenyl)-4,5-dimethyl-1-p-tolyl-1h-imidazole；2-(4-fluorophenyl)-4,5-dimethyl-1-(4-methylphenyl)imidazole
• CAS: 1275593-77-5
• 化学式: C₁₈H₁₇FN₂
• 分子量: 280.345
• InChiKey: OPSVXXKNEVVHQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  氯化铱(III) 水合物 、 2-(4-fluorophenyl)-4,5-dimethyl-1-p-tolyl-1H-imidazole 以 乙二醇乙醚 、 水 为溶剂， 生成 [IrCl((4,5-dimethyl-1-(p-tolyl)-2-(4-fluorophenyl)-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：

  对氟苯甲醛 、 乙烷,三氯氟- 、 2,3-丁二酮 在 ammonium acetate 作用下， 以40%的产率得到2-(4-fluorophenyl)-4,5-dimethyl-1-p-tolyl-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

• Physicochemical studies of molecular hyperpolarizability of imidazole derivatives
  作者：Jayaraman Jayabharathi、Venugopal Thanikachalam、Natesan Srinivasan、Marimuthu Venkatesh Perumal、Karunamoorthy Jayamoorthy

  DOI：10.1016/j.saa.2011.02.024

  日期：2011.6

  A series of substituted imidazoles have been synthesized in very good yield under solvent free condition by grinding 1,2-diketone, arylaldehyde, arylamine and ammonium acetate in the presence of molecular iodine as the catalyst. The short reaction time, good yield and easy workup make this protocol practically and economically attractive and the imidazoles are characterized by NMR spectra, X-ray, mass

  通过在分子碘作为催化剂存在下研磨1,2-二酮，芳醛，芳胺和乙酸铵，在无溶剂条件下以很高的收率合成了一系列取代的咪唑。短的反应时间，良好的收率和简单的后处理使得该方案在实践上和经济上都具有吸引力，并且咪唑通过NMR光谱，X射线，质量和CHN分析来表征。通过中心连接的-N = CC = C-单元的键合轨道（π）和反键合（π*）的占有率的商来分析一系列咪唑的推挽特性。推挽参数与相应的键长d（CN）和d（CC）的良好相关性强烈建议占用商（π* /π）和相应的键长都是用于量化推挽特性和这些化合物的分子超极化率ß（0）。为了支持实验结果，还进行了理论计算（地层热，NLO，NBO和振动分析）。在此背景下，将得出有关色球空间位阻，推挽特性，咪唑的超极化性及其作为NLO材料的应用的合理结论。还进行了NBO和振动分析。在此背景下，将得出有关色球空间位阻，推挽特性，咪唑的超极化性及其作为NLO材料的应用的合理结
• An Intramolecular Charge Transfer Fluorescent Probe: Synthesis, Structure and Selective Fluorescent Sensing of Cu+2
  作者：Jayaraman Jayabharathi、Venugopal Thanikachalam、Natesan Srinivasan、Karunamoorthy Jayamorthy、Marimuthu Venkatesh Perumal

  DOI：10.1007/s10895-011-0876-5

  日期：2011.7

  A series of substituted imidazoles have been synthesized in very good yield under solvent free condition by grinding 1,2-diketone, aromatic aldehyde and ammonium acetate in the presence of molecular iodine as the catalyst. The short reaction time, good yield and easy workup make this protocol practically and economically attractive and characterized by NMR spectra, X-ray, mass and CHN analysis. An excited state intramolecular proton transfer (ESIPT) process in hydroxy imidazoles (dpip and dptip) have been studied using emission spectroscopy and it was detected that the two distinct ground state rotamers are responsible for the normal and the tautomer emissions. 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. DFT analysis about HOMO, HOMO-1, LUMO and LUMO + 1 were carried out 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.

  一系列取代的咪唑成功合成，产率非常好，采用无溶剂条件，通过研磨1,2-二酮、芳香醛和醋酸铵，在分子碘的存在下作为催化剂。短反应时间、高产率和易于操作使这一方法在实际应用和经济上都具有吸引力，并通过核磁共振谱（NMR）、X射线、质谱和碳氢氮分析进行了表征。使用发射光谱研究了羟基咪唑（dpip和dptip）中的激发态分子内质子转移（ESIPT）过程，发现两种不同的基态旋转异构体分别负责正常发射和醇式异构体发射。对咪唑衍生物在基态和激发态下，旋转异构体的能量、偶极矩和电荷分布进行了密度泛函理论（DFT）计算，并进行了讨论。对HOMO、HOMO-1、LUMO和LUMO + 1的DFT分析也进行了讨论。PES计算表明，两个旋转异构体在激发态的相互转化能量障碍要高于基态。
• 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.