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]-2,5-difluorophenyl]benzimidazole | 1334474-38-2

• 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-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]-2,5-difluorophenyl]benzimidazole
• 英文别名: 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]-2,5-difluorophenyl]benzimidazole
• CAS: 1334474-38-2
• 化学式: C₅₂H₄₂F₂N₁₀
• 分子量: 844.969
• InChiKey: XRFQYBDVJHIJPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  64
• 可旋转键数：
  10
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  97.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  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]-2,5-difluorophenyl]benzimidazole 、 [Eu(hexafluoroacetylacetonate)₃(1-methoxy-2-(2-methoxyethoxy)ethane)] 以 氯仿 为溶剂， 生成 [(Eu(hfac)3)2(C6H2F2(C7H3N2(CH2CH3)C5H3NC7H4N2(CH2CH3))2)]
  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：

  2,5-二溴硝基苯 在 四(三苯基膦)钯 、 sodium dithionite 、 三乙胺 、 cesium fluoride 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.3h， 生成 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]-2,5-difluorophenyl]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

文献信息

• Optimizing Sensitization Processes in Dinuclear Luminescent Lanthanide Oligomers: Selection of Rigid Aromatic Spacers
  作者：Jean-François Lemonnier、Laure Guénée、César Beuchat、Tomasz A. Wesolowski、Prasun Mukherjee、David H. Waldeck、Kristy A. Gogick、Stéphane Petoud、Claude Piguet

  DOI：10.1021/ja206806t

  日期：2011.10.12

  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.