1-octyl-2-[6-(2H-tetrazol-5-yl)pyridin-2-yl]benzimidazole | 1609032-99-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-octyl-2-[6-(2H-tetrazol-5-yl)pyridin-2-yl]benzimidazole
• CAS: 1609032-99-6
• 化学式: C₂₁H₂₅N₇
• 分子量: 375.476
• InChiKey: DGYZMRHOAPSFSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  85.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  europium(III) chloride hexahydrate 、 1-octyl-2-[6-(2H-tetrazol-5-yl)pyridin-2-yl]benzimidazole 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.34h， 以85%的产率得到
  参考文献：
  名称：

  Tridentate Benzimidazole-Pyridine-Tetrazolates as Sensitizers of Europium Luminescence

  摘要：

  We report on new anionic tridentate benzimidazole-pyridine-tetrazolate ligands that form neutral 3:1 complexes with trivalent lanthanides. The ligands are UV-absorbing chromophores that sensitize the red luminescence of europium with energy-transfer efficiency of 74-100%. The lifetime and quantum yield of the sensitized europium luminescence increase from 0.5 ms and 12-13% for the as-prepared solids to 2.8 ms and 41% for dichloromethane solution. From analysis of the data, the as-prepared solids can be described as aqua-complexes [Ln(k(3)-ligand)(2)(K-1-ligand)(H2O)x] where the coordinated water molecules are responsible for the strong quenching of the europium luminescence. In solution, the coordinated water molecules are replaced by the nitrogen atoms of the K-1-ligand to give anhydrous complexes [Ln(K-3-ligand)(3)] that exhibit efficient europium luminescence. X-ray structures of the anhydrous complexes confirm that the lanthanide ion (La-III, Eu-III) is nine-coordinate in a distorted tricapped trigonal prismatic environment and that coordination of the lanthanide ion by tetrazolate is weaker than by carboxylate.

  DOI：

  10.1021/ic500267b
• 作为产物：
  描述：

  6-(羟基甲基)吡啶甲醛 在 selenium(IV) oxide 、 甲酸 、 sodium azide 、 sodium dithionite 、 盐酸羟胺 、 sodium formate 、 氯化铵 作用下， 以 1,4-二氧六环 、 乙二醇甲醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.5h， 生成 1-octyl-2-[6-(2H-tetrazol-5-yl)pyridin-2-yl]benzimidazole
  参考文献：
  名称：

  Tridentate Benzimidazole-Pyridine-Tetrazolates as Sensitizers of Europium Luminescence

  摘要：

  We report on new anionic tridentate benzimidazole-pyridine-tetrazolate ligands that form neutral 3:1 complexes with trivalent lanthanides. The ligands are UV-absorbing chromophores that sensitize the red luminescence of europium with energy-transfer efficiency of 74-100%. The lifetime and quantum yield of the sensitized europium luminescence increase from 0.5 ms and 12-13% for the as-prepared solids to 2.8 ms and 41% for dichloromethane solution. From analysis of the data, the as-prepared solids can be described as aqua-complexes [Ln(k(3)-ligand)(2)(K-1-ligand)(H2O)x] where the coordinated water molecules are responsible for the strong quenching of the europium luminescence. In solution, the coordinated water molecules are replaced by the nitrogen atoms of the K-1-ligand to give anhydrous complexes [Ln(K-3-ligand)(3)] that exhibit efficient europium luminescence. X-ray structures of the anhydrous complexes confirm that the lanthanide ion (La-III, Eu-III) is nine-coordinate in a distorted tricapped trigonal prismatic environment and that coordination of the lanthanide ion by tetrazolate is weaker than by carboxylate.

  DOI：

  10.1021/ic500267b

文献信息

• Tridentate Benzimidazole-Pyridine-Tetrazolates as Sensitizers of Europium Luminescence
  作者：Nail M. Shavaleev、Svetlana V. Eliseeva、Rosario Scopelliti、Jean-Claude G. Bünzli

  DOI：10.1021/ic500267b

  日期：2014.5.19

  We report on new anionic tridentate benzimidazole-pyridine-tetrazolate ligands that form neutral 3:1 complexes with trivalent lanthanides. The ligands are UV-absorbing chromophores that sensitize the red luminescence of europium with energy-transfer efficiency of 74-100%. The lifetime and quantum yield of the sensitized europium luminescence increase from 0.5 ms and 12-13% for the as-prepared solids to 2.8 ms and 41% for dichloromethane solution. From analysis of the data, the as-prepared solids can be described as aqua-complexes [Ln(k(3)-ligand)(2)(K-1-ligand)(H2O)x] where the coordinated water molecules are responsible for the strong quenching of the europium luminescence. In solution, the coordinated water molecules are replaced by the nitrogen atoms of the K-1-ligand to give anhydrous complexes [Ln(K-3-ligand)(3)] that exhibit efficient europium luminescence. X-ray structures of the anhydrous complexes confirm that the lanthanide ion (La-III, Eu-III) is nine-coordinate in a distorted tricapped trigonal prismatic environment and that coordination of the lanthanide ion by tetrazolate is weaker than by carboxylate.