6-(1-Octylbenzimidazol-2-yl)pyridine-2-carbaldehyde | 1201193-56-7

• 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: 6-(1-Octylbenzimidazol-2-yl)pyridine-2-carbaldehyde
• 英文别名: 6-(1-octylbenzimidazol-2-yl)pyridine-2-carbaldehyde
• CAS: 1201193-56-7
• 化学式: C₂₁H₂₅N₃O
• 分子量: 335.449
• InChiKey: MKSHBWQKPBHVEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(1-Octylbenzimidazol-2-yl)pyridine-2-carbaldehyde 在 甲酸 、 sodium azide 、 盐酸羟胺 、 sodium formate 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 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
• 作为产物：
  描述：

  6-(羟基甲基)吡啶甲醛 在 selenium(IV) oxide 、 sodium dithionite 作用下， 以 1,4-二氧六环 、 乙二醇甲醚 、 水 为溶剂， 反应 24.0h， 生成 6-(1-Octylbenzimidazol-2-yl)pyridine-2-carbaldehyde
  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

• Designing Simple Tridentate Ligands for Highly Luminescent Europium Complexes
  作者：Nail M. Shavaleev、Svetlana V. Eliseeva、Rosario Scopelliti、Jean-Claude G. Bünzli

  DOI：10.1002/chem.200901996

  日期：2009.10.19

  pyridine‐2‐carboxylic acids have been prepared with a halogen, methyl or alkoxy group in the 6‐position of the benzimidazole ring, which additionally contains a solubilising N‐alkyl chain. The ligands form neutral homoleptic nine‐coordinate lanthanum, europium and terbium complexes as established from X‐ray crystallographic analysis of eight structures. The coordination polyhedron around the lanthanide ion

  制备了一系列三齿苯并咪唑取代的吡啶-2-羧酸，在苯并咪唑环的6位带有卤素，甲基或烷氧基，其中还含有可溶的N烷基链。配体形成中性的九坐标镧，euro和ter络合物，这是通过对八个结构的X射线晶体学分析确定的。镧系元素离子周围的配位多面体接近于三重三角棱镜，其配体以上-下-下的方式排列。配位体充当络合物中的集光生色团，其最大吸收范围为321–341 nm（ε =（4.9–6.0）×10 4  M -1  cm -1）以及21,300至18,800 cm -1之间的三重态能量; 最大的红移发生在溴和电子给体的烷氧基取代基上。配体有效地敏化铕的发光与整体的量子产率（）和观察到的寿命（τ OBS）分别达到71％和3.00毫秒，在固体状态下和52％和2.81毫秒，在CH 2氯2在室温下。铕（的辐射寿命5 d 0）电平量τ弧度= 3.6-4.6毫秒和敏化效率η SENS = （τ弧度/τ OBS）对于大
• 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.