2-(coumarinyl-6-azo)-4-methyl imidazole | 1310359-46-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 2-(coumarinyl-6-azo)-4-methyl imidazole
• 英文别名: 2-(coumarin-6-ylazo)-4-methylimidazole；2-(coumarinyl-6-azo)-4-methylimidazole；2-(coumaryl-6-azo)-4-methyl-imidazole；H-2-Cai-4-Me；4-Me-LH；CZ-4-Me-H；6-[(5-methyl-1H-imidazol-2-yl)diazenyl]chromen-2-one
• CAS: 1310359-46-6
• 化学式: C₁₃H₁₀N₄O₂
• 分子量: 254.248
• InChiKey: OAAQXBDAEPASLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(coumarinyl-6-azo)-4-methyl imidazole 在 sodium hydride 作用下， 以 四氢呋喃 、 paraffin oil 为溶剂， 反应 11.0h， 生成
  参考文献：
  名称：

  氢化羰基（的香豆素基偶氮咪唑基配合物：光谱和结构表征，氧化催化，光伏效应和密度泛函理论计算

  摘要：

  OS（II）香豆素azoimidazoles的氢化羰基络合物，[奥什（CO）（PPH 3）2（CZ-4R-R'）] 0 / +（3，4）（CZ-R-H = 2-（香豆素-6- [-偶氮] -4-取代的咪唑或1-烷基-2-（香豆基-6-偶氮）-4-取代的咪唑）是通过光谱数据和其中一种配合物的单晶X射线数据[[ Osh（CO）（PPh 3）2（CZ‐4‐Ph）]（3c）（CZ‐4‐Ph = 2‐（香豆基‐6‐偶氮）‐4‐苯基咪唑酸酯），确认了结构。的配合物表现出更高的发射（量子产率φ  = 0.0163-0.16）和更长的寿命（τ  = 1.4-10.3纳秒）比游离配体（φ = 0.0012–0.0185和τ  = 0.685–1.306 ns）。循环伏安法显示，[Os（III）/ Os（II）]在0.67–0.94 V时为准可逆金属氧化，[Os（IV）/ Os（III）]在1.21–1.36

  DOI：

  10.1002/aoc.3435
• 作为产物：
  描述：

  2H-1-苯并吡喃-2-酮,6-氨基- 在 盐酸 、 sodium carbonate 作用下， 以 水 为溶剂， 生成 2-(coumarinyl-6-azo)-4-methyl imidazole
  参考文献：
  名称：

  Structure, photophysics, electrochemistry and DFT calculations of [RuH(CO)(PPh3)2(coumarinyl-azo-imidazole)]

  摘要：

  2-(Coumarinyl-6-azo)-4-R-imidazole (4-R-LH, 1) and 4-(coumarinyl-6-azo)-5-R-imidazole (5-R-LH, 2) (R = H, Me, Ph) are two classes of -N=N-C=N- ligands used to synthesize [RuH(CO)(PPh3)(2)(4-R-L)] (3) and [RuH(CO)(PPh3)(2)(5-R-LH)Cl] (4). The characterization of the complexes has been done by elemental analysis and spectroscopic methods, and X-ray characterization is reported for one representative complex. The redox properties of the complexes were studied by cyclic voltammetry. They are emissive at room temperature. DFT and time dependent-DFT calculations were performed to explain the electronic structure, spectral and redox properties of the complexes. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2013.01.041

文献信息

• Ir(I)–carbonyl complexes of coumarinazoimidazoles: Synthesis structure, electrochemistry, photophysical properties and DFT calculations
  作者：Papia Datta、Dibakar Sardar、Partha Mitra、Chittaranjan Sinha

  DOI：10.1016/j.poly.2011.03.021

  日期：2011.5

  The reactions of Vaska's complex [IrCl(CO)(PPh3)(2)] with 2-(coumaryl-6-azo)imidazole (CZ-H) and its derivatives (CZ-X) have synthesized [Ir(CZ)(CO)(PPh3)(2)] and [Ir(CZ-X)(CO)(PPh3)(2)]. All the complexes have been characterized by FT-IR, UV-Vis, NMR and FAB-MS spectroscopy. The structural confirmation has been done in one case, by a single crystal X-ray diffraction study, which shows a distorted square pyramidal geometry around the central It atom. The complexes are emissive at room temperature. The cyclic voltammetry of the complexes shows a metal centered irreversible oxidation and ligand centered quasireversible reduction couples. To get an insight into the electronic structure, absorption spectra and electrochemical properties, detailed calculations on all three complexes have been performed at the DFT level. (C) 2011 Elsevier Ltd. All rights reserved.
• Structure, photophysics, electrochemistry and DFT calculations of [RuH(CO)(PPh3)2(coumarinyl-azo-imidazole)]
  作者：Papia Datta、Dibakar Sardar、Rajat Saha、Tapan Kumar Mondal、Chittaranjan Sinha

  DOI：10.1016/j.poly.2013.01.041

  日期：2013.4

  2-(Coumarinyl-6-azo)-4-R-imidazole (4-R-LH, 1) and 4-(coumarinyl-6-azo)-5-R-imidazole (5-R-LH, 2) (R = H, Me, Ph) are two classes of -N=N-C=N- ligands used to synthesize [RuH(CO)(PPh3)(2)(4-R-L)] (3) and [RuH(CO)(PPh3)(2)(5-R-LH)Cl] (4). The characterization of the complexes has been done by elemental analysis and spectroscopic methods, and X-ray characterization is reported for one representative complex. The redox properties of the complexes were studied by cyclic voltammetry. They are emissive at room temperature. DFT and time dependent-DFT calculations were performed to explain the electronic structure, spectral and redox properties of the complexes. (C) 2013 Elsevier Ltd. All rights reserved.
• Coumarinyl azoimidazolyl complexes of osmium(II) hydridocarbonyls: spectroscopic and structural characterization, oxidation catalysis, photovoltaic effect and density functional theory computation
  作者：Papia Datta、Dibakar Sardar、Uttam Panda、Ajanta Halder、Nabin Baran Manik、Chun-Jung Chen、Chittaranjan Sinha

  DOI：10.1002/aoc.3435

  日期：2016.5

  Os(II) hydridocarbonyl complexes of coumarinyl azoimidazoles, [Osh(CO)(PPh3)2(CZ‐4R‐R′)]0/+ (3, 4) (CZ‐R‐H = 2‐(coumarinyl‐6‐azo)‐4‐substituted imidazole or 1‐alkyl‐2‐(coumarinyl‐6‐azo)‐4‐substituted imidazole), were characterized from spectroscopic data and the single‐crystal X‐ray data for one of the complexes, [Osh(CO)(PPh3)2(CZ‐4‐Ph)] (3c) (CZ‐4‐Ph = 2‐(coumarinyl‐6‐azo)‐4‐phenylimidazolate), confirmed

  OS（II）香豆素azoimidazoles的氢化羰基络合物，[奥什（CO）（PPH 3）2（CZ-4R-R'）] 0 / +（3，4）（CZ-R-H = 2-（香豆素-6- [-偶氮] -4-取代的咪唑或1-烷基-2-（香豆基-6-偶氮）-4-取代的咪唑）是通过光谱数据和其中一种配合物的单晶X射线数据[[ Osh（CO）（PPh 3）2（CZ‐4‐Ph）]（3c）（CZ‐4‐Ph = 2‐（香豆基‐6‐偶氮）‐4‐苯基咪唑酸酯），确认了结构。的配合物表现出更高的发射（量子产率φ  = 0.0163-0.16）和更长的寿命（τ  = 1.4-10.3纳秒）比游离配体（φ = 0.0012–0.0185和τ  = 0.685–1.306 ns）。循环伏安法显示，[Os（III）/ Os（II）]在0.67–0.94 V时为准可逆金属氧化，[Os（IV）/ Os（III）]在1.21–1.36