4,5-dimethyl-1,2-diphenyl-1H-imidazole | 30234-71-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,5-dimethyl-1,2-diphenyl-1H-imidazole
• 英文别名: 4,5-dimethyl-1,2-diphenylimidazole
• CAS: 30234-71-0
• 化学式: C₁₇H₁₆N₂
• 分子量: 248.327
• InChiKey: APNVXOXHGCDTPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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-1,2-diphenyl-1H-imidazole 以 乙二醇乙醚 、 水 为溶剂， 生成
  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：

  在 溶剂黄146 、 锌 作用下， 反应 3.0h， 以4.9 g的产率得到4,5-dimethyl-1,2-diphenyl-1H-imidazole
  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

文献信息

• Catalyst-Free One-Pot Four Component Synthesis of Polysubstituted Imidazoles in Neutral Ionic Liquid 1-Butyl-3-methylimidazolium Bromide
  作者：Alireza Hasaninejad、Abdolkarim Zare、Mohsen Shekouhy、Javad Ameri Rad

  DOI：10.1021/cc100097m

  日期：2010.11.8

  A catalyst-free one-pot four component methodology for the synthesis of 1,2,4,5-substituted imidazoles under conventional heating and microwave irradiation using 1-butyl-3-methylimidazolium bromide, [Bmim]Br, as a neutral reaction media is described. A broad range of structurally diverse aldehydes (aromatic aldehydes bearing electron withdrawing and/or electron releasing groups as well as heteroaromatic

  在传统的加热和微波辐射下，使用1-丁基-3-甲基咪唑鎓溴化物[Bmim] Br作为中性反应介质的无催化剂一锅四组分方法，用于合成1,2,4,5-取代的咪唑描述。成功应用了多种结构多样的醛（带有吸电子和/或电子释放基团的芳族醛以及杂芳族醛）和伯胺（芳族和脂族），并以良好的产率获得了相应的产品，且无副产物。
• Iridium(III) Complexes with Orthometalated Phenylimidazole Ligands Subtle Turning of Emission to the Saturated Green Colour
  作者：Jayaraman Jayabharathi、Venugopal Thanikachalam、Kanagarathinam Saravanan、Natesan Srinivasan

  DOI：10.1007/s10895-010-0737-7

  日期：2011.3

  A series of novel six iridium complexes (1–6) bearing two substituted phenylimidazole and an additional acetylacetone as the third co-auxilary ligand are reported. The lowest absorption band for all iridium complexes consist of a mixture of heavy atom Ir(III) enhanced 3MLCT and 3 π-π* transitions and the phosphorescent peak wavelength can be fine-tuned to cover the spectral range 455–518 nm with high quantum efficiencies. The peak wavelength of the dopants can be finely tuned depending upon the electronic properties of the substituents. On the basis of onset potentials of the oxidation and reduction, the HOMO-LUMO energies were calculated and the reported iridium complexes emit green light with exceeding higher efficiency.

  报告了一系列新颖的六种铱配合物（1-6），它们含有两个取代的苯基咪唑和一个额外的乙酰丙酮作为第三个共辅助配体。所有铱配合物的最低吸收带均由重金属铱（III）增强的 3MLCT 和 3 π-π* 转变组成，磷光峰波长可微调以覆盖 455-518 nm 的光谱范围，并具有较高的量子效率。掺杂剂的峰值波长可根据取代基的电子特性进行微调。根据氧化和还原的起始电位，计算出了 HOMO-LUMO 能量，所报告的铱复合物能以更高的效率发出绿光。
• Synthesis and Photophysics of Some Novel Imidazole Derivatives Used as Sensitive Fluorescent Chemisensors
  作者：Kanagarathinam Saravanan、Natesan Srinivasan、Venugopal Thanikachalam、Jayaraman Jayabharathi

  DOI：10.1007/s10895-010-0690-5

  日期：2011.1

  Some novel imidazole derivatives were developed for highly sensitive chemisensors for transition metal ions. Since these compounds are sensitive to different external stimulations such as UV irradiation, heat, increasing pressure and changing the environmental pH causing colour change and so they can be used as a ′multi-way′ optically switchable material. A prominent fluorescence enhancement was found

  一些新型咪唑衍生物被开发用于过渡金属离子的高灵敏度化学传感器。由于这些化合物对不同的外部刺激敏感，例如紫外线照射、热量、压力增加和环境 pH 值的变化导致颜色变化，因此它们可以用作“多路”光可切换材料。在过渡金属离子如 Hg 2+、Pb 2+和 Cu 2+存在下发现显着的荧光增强这被认为是由于抑制了化学传感器中 n-π* 状态的无辐射跃迁。自然键轨道分析 (NBO) 证实了 dmphnpi 中 CH....O 分子内氢键的存在。还计算了 Mulliken、NBO 电荷分析和 HOMO-LUMO 能量。通过实验和理论研究了所研究分子的电偶极矩 ( μ ) 和第一超极化率 ( β ) 值，表明合成的分子具有非零值的微观非线性光学 (NLO) 行为。为了找出偶极矩和能量，进行了基态和激发态 DFT 计算。
• Organic electroluminescence device
  申请人：UDC Ireland

  公开号：US10454042B2

  公开（公告）日：2019-10-22

  An object of the present invention is to provide an organic electroluminescence device having excellent light emission efficiency and durability, in particular, durability when driving at a high temperature. Provided is an organic electroluminescence device including on a substrate a pair of electrodes, and at least one layer of an organic layer including a light emitting layer containing a light emitting material disposed between the electrodes, wherein the light emitting layer includes at least each one of specific indolocarbazole derivatives and specific condensed ring metal complexes.

  本发明的目的是提供一种有机电致发光器件，该器件具有优异的发光效率和耐用性，特别是在高温驱动时的耐用性。本发明提供了一种有机电致发光器件，包括在基底上的一对电极，以及至少一层有机层，该有机层包括设置在电极之间的包含发光材料的发光层，其中发光层包括特定吲哚咔唑衍生物和特定缩合环金属配合物中的至少一种。
• COMPOUND FOR ORGANIC ELECTROLUMINESCENT ELEMENT AND ORGANIC ELECTROLUMINESCENT ELEMENT
  申请人：Nippon Steel Chemical Co., Ltd.

  公开号：EP1956022B1

  公开（公告）日：2012-07-25