5-bromo-1-ethyl-2-(6-(1-ethyl-1H-benzo[d]imidazol-2-yl)pyridin-2-yl)-1H-benzo[d]imidazole | 1334474-36-0

• 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: 5-bromo-1-ethyl-2-(6-(1-ethyl-1H-benzo[d]imidazol-2-yl)pyridin-2-yl)-1H-benzo[d]imidazole
• CAS: 1334474-36-0
• 化学式: C₂₃H₂₀BrN₅
• 分子量: 446.349
• InChiKey: HYIMEUAKTIGTLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.92
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  48.53
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-bromo-1-ethyl-2-(6-(1-ethyl-1H-benzo[d]imidazol-2-yl)pyridin-2-yl)-1H-benzo[d]imidazole 、 1,4-苯二硼酸 在 四(三苯基膦)钯 、 cesium fluoride 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 24.3h， 以71%的产率得到1-Ethyl-2-[6-(1-ethylbenzimidazol-2-yl)pyridin-2-yl]-5-[4-[1-ethyl-2-[6-(1-ethylbenzimidazol-2-yl)pyridin-2-yl]benzimidazol-5-yl]phenyl]benzimidazole
  参考文献：
  名称：

  Optimizing Sensitization Processes in Dinuclear Luminescent Lanthanide Oligomers: Selection of Rigid Aromatic Spacers

  摘要：

  This work illustrates a simple approach for optimizing the lanthanide luminescence in molecular dinuclear lanthanide complexes and identifies a particular multidentate europium complex as the best candidate for further incorporation into polymeric materials. The central phenyl ring in the bis-tridentate model ligands L3-L5, which are substituted with neutral (X = H, L3), electron-withdrawing (X = F, L4), or electron-donating (X = OCH3, L5) groups, separates the 2,6-bis(benzimidazol-2-yl)pyridine binding units of linear oligomeric multi-tridentate ligand strands that are designed for the complexation of luminescent trivalent lanthanides, Ln(III). Reactions of L3-L5 with [Ln(hfac)(3)(diglyme)] (hfac(-) is the hexafluoroacetylacetonate anion) produce saturated single-stranded dumbbell-shaped complexes [Ln(2)(Lk)(hfac)(6)] (k = 3-5), in which the lanthanide ions of the two nine-coordinate neutral [N(3)Ln(hfac)(3)] units are separated by 12-14 angstrom. The thermodynamic affinities of [Ln(hfac)(3)] for the tridentate binding sites in L3-L5 are average (6.6 <= log(beta(Y,Lk)(2,1)) <= 8.4) but still result in 15-30% dissociation at millimolar concentrations in acetonitrile. In addition to the empirical solubility trend found in organic solvents (L4 > L3 >> L5), which suggests that the 1,4-difluorophenyl spacer in L4 is preferable, we have developed a novel tool for deciphering the photophysical sensitization processes operating in [Eu-2(Lk)(hfac)(6)]. A simple interpretation of the complete set of rate constants characterizing the energy migration mechanisms provides straightforward objective criteria for the selection of [Eu-2(L4)(hfac)(6)] as the most promising building block.

  DOI：

  10.1021/ja206806t
• 作为产物：
  描述：

  4-溴-N-乙基-2-硝基苯胺 在 sodium dithionite 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 5-bromo-1-ethyl-2-(6-(1-ethyl-1H-benzo[d]imidazol-2-yl)pyridin-2-yl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Optimizing Sensitization Processes in Dinuclear Luminescent Lanthanide Oligomers: Selection of Rigid Aromatic Spacers

  摘要：

  This work illustrates a simple approach for optimizing the lanthanide luminescence in molecular dinuclear lanthanide complexes and identifies a particular multidentate europium complex as the best candidate for further incorporation into polymeric materials. The central phenyl ring in the bis-tridentate model ligands L3-L5, which are substituted with neutral (X = H, L3), electron-withdrawing (X = F, L4), or electron-donating (X = OCH3, L5) groups, separates the 2,6-bis(benzimidazol-2-yl)pyridine binding units of linear oligomeric multi-tridentate ligand strands that are designed for the complexation of luminescent trivalent lanthanides, Ln(III). Reactions of L3-L5 with [Ln(hfac)(3)(diglyme)] (hfac(-) is the hexafluoroacetylacetonate anion) produce saturated single-stranded dumbbell-shaped complexes [Ln(2)(Lk)(hfac)(6)] (k = 3-5), in which the lanthanide ions of the two nine-coordinate neutral [N(3)Ln(hfac)(3)] units are separated by 12-14 angstrom. The thermodynamic affinities of [Ln(hfac)(3)] for the tridentate binding sites in L3-L5 are average (6.6 <= log(beta(Y,Lk)(2,1)) <= 8.4) but still result in 15-30% dissociation at millimolar concentrations in acetonitrile. In addition to the empirical solubility trend found in organic solvents (L4 > L3 >> L5), which suggests that the 1,4-difluorophenyl spacer in L4 is preferable, we have developed a novel tool for deciphering the photophysical sensitization processes operating in [Eu-2(Lk)(hfac)(6)]. A simple interpretation of the complete set of rate constants characterizing the energy migration mechanisms provides straightforward objective criteria for the selection of [Eu-2(L4)(hfac)(6)] as the most promising building block.

  DOI：

  10.1021/ja206806t

文献信息

• Perfluorinated Aromatic Spacers for Sensitizing Europium(III) Centers in Dinuclear Oligomers: Better than the Best by Chemical Design?
  作者：Jean-François Lemonnier、Lucille Babel、Laure Guénée、Prasun Mukherjee、David H. Waldeck、Svetlana V. Eliseeva、Stéphane Petoud、Claude Piguet

  DOI：10.1002/anie.201205082

  日期：2012.11.5

  Transfer news: The use of a simple method allows the various sensitization steps in EuIII‐containing complexes to be deciphered. Incorporation of an increasing number of electron‐withdrawing fluorine atoms on the rigid and electronically tunable phenyl spacer between two tridentate binding units (see picture, red O, dark blue N) affects the quantum yield, intersystem crossing, and energy‐transfer processes

  Transfer news : 使用简单的方法可以破译含Eu III的复合物中的各种敏化步骤。在两个三齿结合单元（见图，红色 O，深蓝色 N）之间的刚性和电子可调苯基间隔基上掺入越来越多的吸电子氟原子会影响量子产率、系统间交叉和能量转移过程理性的方式。