(4-溴苯基)-(1-甲基咪唑-2-基)二氮烯 | 72908-93-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (4-溴苯基)-(1-甲基咪唑-2-基)二氮烯
• 英文名称: 1-Methyl-2-(p-bromphenylazo)-imidazol
• 英文别名: N(1)-methyl-2-(4'-bromophenylazo)imidazole；2-(4-bromo-phenylazo)-1-methyl-1H-imidazole；2-[(E)-(4-Bromophenyl)diazenyl]-1-methyl-1H-imidazole；(4-bromophenyl)-(1-methylimidazol-2-yl)diazene
• CAS: 72908-93-1
• 化学式: C₁₀H₉BrN₄
• 分子量: 265.112
• InChiKey: CUWSZEVHGHXQEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0) 、 (4-溴苯基)-(1-甲基咪唑-2-基)二氮烯 以 正己烷 为溶剂， 以59%的产率得到cis-tetracarbonyl(N(1)-methyl-2-(4'-bromophenylazo)imidazole)
  参考文献：
  名称：

  Synthesis and characterization of cis-Mo(CO)4(L–L′) and cis-Mo(CO)2(L–L′)2 complexes of N(1)-methyl-2-(arylazo)imidazoles (L–L′). Correlations of spectroscopic data with substituent effects

  摘要：

  N(1)-Methyl-2-(p-X-phenylazo)imidazoles (L-L'; X = CH3O, CH3, H, Br, CF3, NO2) react with cis -(norbornadiene)MO(CO)(4) and MO(CO)(3)(CH3CN)(3) to provide the complexes CiS-MO(CO)(4)(L-L) (X = CH3O, CH3, H, Br, CF3, NO2) and CiS-MO(CO)(2)(L-L')(2) (X = CH3, H, Br, CF3), respectively. The complexes were characterized by visible and infrared spectroscopy, by H-1-, C-13- and Mo-95-NMR spectroscopy, and by cyclic voltammetry. Correlations among the data and correlations of the data with the Hammett sigma parameter within each set of complexes were investigated and are generally very good. These data, as well as the inability to synthesize complexes of the type Mo(L-L')(3), indicate that 2-(arylazo)imidazoles are less effective ligands at stabilizing complexes of zerovalent metals than are 2-(arylazo)pyridines. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(03)00793-9
• 作为产物：
  描述：

  4-溴苯胺 在 盐酸 、 potassium carbonate 、 sodium nitrite 作用下， 以 水 、 丙酮 为溶剂， 反应 13.17h， 生成 (4-溴苯基)-(1-甲基咪唑-2-基)二氮烯
  参考文献：
  名称：

  分子偶氮咪唑光开关：通过取代调节性能

  摘要：

  通过便捷的合成路线设计并制备了基于NH-和N-甲基咪唑的偶氮咪唑光开关。通过 XRD 分析、循环伏安法、热分析、紫外-可见吸收光谱和 DFT 计算对这些偶氮化合物进行了研究。光开关主要受咪唑N取代的影响，( Z ) 异构体的半衰期在数十秒（NH-咪唑）与数十小时（N-甲基咪唑）之间。N-甲基咪唑开关可以通过改变附加取代基（酰基、溴、三氟甲基和五氟硫基）的电子效应来进一步调节。后一组被证明在稳定 ( Z )-异构体方面特别有趣。与 ( E )-异构体 (β E / Z = 3.82 ) 相比，其半衰期长 (∼24 h)、光转化率高 (89 %) 和非线性光学响应减弱，这 表明引入 SF 5基团是一种非常有用的策略在分子开关的结构中。总之，这项详细的研究表明，通过（防止）咪唑互变异构以及改变附加取代基的电子效应，可以在很大程度上显着调节偶氮咪唑的光开关特性。

  DOI：

  10.1016/j.jphotochem.2023.115390

文献信息

• Synthesis and characterization of cis-Mo(CO)4(L–L′) and cis-Mo(CO)2(L–L′)2 complexes of N(1)-methyl-2-(arylazo)imidazoles (L–L′). Correlations of spectroscopic data with substituent effects
  作者：Martin N Ackermann、Marisa P Robinson、Ian A Maher、Eric B LeBlanc、Richard V Raz

  DOI：10.1016/s0022-328x(03)00793-9

  日期：2003.10

  N(1)-Methyl-2-(p-X-phenylazo)imidazoles (L-L'; X = CH3O, CH3, H, Br, CF3, NO2) react with cis -(norbornadiene)MO(CO)(4) and MO(CO)(3)(CH3CN)(3) to provide the complexes CiS-MO(CO)(4)(L-L) (X = CH3O, CH3, H, Br, CF3, NO2) and CiS-MO(CO)(2)(L-L')(2) (X = CH3, H, Br, CF3), respectively. The complexes were characterized by visible and infrared spectroscopy, by H-1-, C-13- and Mo-95-NMR spectroscopy, and by cyclic voltammetry. Correlations among the data and correlations of the data with the Hammett sigma parameter within each set of complexes were investigated and are generally very good. These data, as well as the inability to synthesize complexes of the type Mo(L-L')(3), indicate that 2-(arylazo)imidazoles are less effective ligands at stabilizing complexes of zerovalent metals than are 2-(arylazo)pyridines. (C) 2003 Elsevier B.V. All rights reserved.
• Molecular azo–imidazole photoswitches: Property tuning by substitution
  作者：Veronika Jelínková、Angela Dellai、Martina Vachtlová、Michaela Fecková、Jan Podlesný、Milan Klikar、Frédéric Castet、Aleš Růžička、Patrik Pařík、Oldřich Pytela、Filip Bureš

  DOI：10.1016/j.jphotochem.2023.115390

  日期：2024.4

  range of tens of seconds (NH-imidazoles) vs. tens of hours (N-methylimidazoles). N-Methylimidazole switches can be further tuned by altering electronic effects of the appended substituents (acyl, bromine, trifluoromethyl and pentafluorosulfanyl). The latter group proved to be particularly interesting in stabilizing (Z)–isomer. Its large half-life (∼24 h), high photoconversion (89 %) and diminished nonlinear

  通过便捷的合成路线设计并制备了基于NH-和N-甲基咪唑的偶氮咪唑光开关。通过 XRD 分析、循环伏安法、热分析、紫外-可见吸收光谱和 DFT 计算对这些偶氮化合物进行了研究。光开关主要受咪唑N取代的影响，( Z ) 异构体的半衰期在数十秒（NH-咪唑）与数十小时（N-甲基咪唑）之间。N-甲基咪唑开关可以通过改变附加取代基（酰基、溴、三氟甲基和五氟硫基）的电子效应来进一步调节。后一组被证明在稳定 ( Z )-异构体方面特别有趣。与 ( E )-异构体 (β E / Z = 3.82 ) 相比，其半衰期长 (∼24 h)、光转化率高 (89 %) 和非线性光学响应减弱，这 表明引入 SF 5基团是一种非常有用的策略在分子开关的结构中。总之，这项详细的研究表明，通过（防止）咪唑互变异构以及改变附加取代基的电子效应，可以在很大程度上显着调节偶氮咪唑的光开关特性。