[3-Ethyl-2-[6-[1-ethyl-6-(3,4,5-tridodecoxybenzoyl)oxybenzimidazol-2-yl]pyridin-2-yl]benzimidazol-5-yl] 3,4,5-tridodecoxybenzoate | 845737-43-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [3-Ethyl-2-[6-[1-ethyl-6-(3,4,5-tridodecoxybenzoyl)oxybenzimidazol-2-yl]pyridin-2-yl]benzimidazol-5-yl] 3,4,5-tridodecoxybenzoate
• 英文别名: [3-ethyl-2-[6-[1-ethyl-6-(3,4,5-tridodecoxybenzoyl)oxybenzimidazol-2-yl]pyridin-2-yl]benzimidazol-5-yl] 3,4,5-tridodecoxybenzoate
• CAS: 845737-43-1
• 化学式: C₁₀₉H₁₇₃N₅O₁₀
• 分子量: 1713.6
• InChiKey: JXVNWJGJFQHQEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  40
• 重原子数：
  124
• 可旋转键数：
  82
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  157
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  、 [3-Ethyl-2-[6-[1-ethyl-6-(3,4,5-tridodecoxybenzoyl)oxybenzimidazol-2-yl]pyridin-2-yl]benzimidazol-5-yl] 3,4,5-tridodecoxybenzoate 以 二氯甲烷 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Structural, Thermodynamic, and Mesomorphic Consequences of Replacing Nitrates with Trifluoroacetate Counteranions in Ternary Lanthanide Complexes with Hexacatenar Tridentate Ligands

  摘要：

  The promesogenic hexacatenar tridentate ligands L3(Cn) (I shape) and L4(Cn) (V shape) react with trivalent lanthanide trifluoroacetates, Ln((CF3CO2)(3), to give either monometallic [Ln(Li-Cn)(CF3CO2)(3)] or trifluoroacetato-bridged bimetallic [Ln(Li-Cn)(CF3CO2)(3)](2) complexes in the solid state, as exemplified by the crystal structures of [Lu(L4(C0))(CF3CO2)(3)-(H2O)], [Lu(L4(C0))(CF3CO2)(3)](2), and [La(L3(C4))(CF3CO2)(3)](2). Although the dimerization process is influenced by the competiting complexation of anions or solvent molecules, the coordination of CF3CO2- instead of NO3- to Ln(III) produces a significant lengthening of the Ln-N(ligand) bond distances. This translates into a considerable decrease of the affinity of the Li-C12 (i = 3, 4) ligands for Ln(CF3CO2)(3) in solution, thus leading to significant dissociation of the [Ln(Li-C12)(CF3CO2)(3)] complexes at millimolar concentrations. The thermal properties of these complexes also suffer from their limited thermodynamic stability, and the thermotropic liquid crystalline phases produced at high temperatures reflect mixtures of different species. However, a hexagonal columnar organization characterizes the main component in the mesophases obtained with [Ln(L3(C12))(CF3CO2)(3)] at high temperature. A tentative interpretation of the small-angle X-ray scaterring (SAXS) profiles suggests that disklike dimers of [Ln(L3(C12))(CF3CO2)(3)](2) are packed along the columnar axes. For [Ln(L4(C12))(CF3CO2)(3)], SAXS profiles are compatible with a lamellar organization in the mesophases originating from the existence of rodlike dimers of [Ln(L4(C12))(CF3CO2)(3)](2) as the major component in the liquid-crystal state.

  DOI：

  10.1021/ic052017u
• 作为产物：
  描述：

  苯甲酸,3,4,5-三(十二烷氧基)- 、 2,6-bis(1-ethyl-6-hydroxybenzimidazol-2-yl)pyridine 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 [3-Ethyl-2-[6-[1-ethyl-6-(3,4,5-tridodecoxybenzoyl)oxybenzimidazol-2-yl]pyridin-2-yl]benzimidazol-5-yl] 3,4,5-tridodecoxybenzoate
  参考文献：
  名称：

  Molecular Control of Macroscopic Cubic, Columnar, and Lamellar Organizations in Luminescent Lanthanide-Containing Thermotropic Liquid Crystals

  摘要：

  The connection of lipophilic gallic acid derivatives at the 5,5'- or 6,6'-positions of the rigid 2,6bis(1-ethyl-benzimidazol-2-yl)pyridine core provides two pro-mesogenic tridentate ligands L10 and L12, whose molecular shapes, anisometries, and directional intermolecular pi-stacking can be tuned. X-ray diffraction data in the crystalline state, combined with solution H-1 NMR measurements, show that complexation with trivalent lanthanides, Ln(III), produces the neutral hemi-disklike complexes [Ln(Li)(NO3)(3)] (i = 10, 12), which dimerize to give the rodlike bimetallic complexes [Ln(2)(Li)(2)(NO3)(6)] at lower temperature. The relevant thermodynamic parameters for the latter process depend on the nature of the ligand, the size of the metal ion, and the strength of the intermolecular interactions involved in the condensed phase. These three-dimensional models obtained for the complexes in the crystals and in solution are eventually confronted with small-angle XRD profiles recorded in the intermediate thermotropic liquid crystalline phase, in which the rigidity of the packed polyaromatic cores is maintained, while the alkyl chains are molten. According to the specific geometries and nuclearities of the molecular complexes, three types of mesophases (lamellar, columnar, and cubic) can be induced, which provides a direct correlation between the microscopic arrangements and the macroscopic ordering in lanthanicle-containing metallomesogens.

  DOI：

  10.1021/ja0446101

文献信息

• Molecular Control of Macroscopic Cubic, Columnar, and Lamellar Organizations in Luminescent Lanthanide-Containing Thermotropic Liquid Crystals
  作者：Emmanuel Terazzi、Stéphane Torelli、Gérald Bernardinelli、Jean-Pierre Rivera、Jean-Marc Bénech、Cyril Bourgogne、Bertrand Donnio、Daniel Guillon、Daniel Imbert、Jean-Claude G. Bünzli、André Pinto、Damien Jeannerat、Claude Piguet

  DOI：10.1021/ja0446101

  日期：2005.1.1

  The connection of lipophilic gallic acid derivatives at the 5,5'- or 6,6'-positions of the rigid 2,6bis(1-ethyl-benzimidazol-2-yl)pyridine core provides two pro-mesogenic tridentate ligands L10 and L12, whose molecular shapes, anisometries, and directional intermolecular pi-stacking can be tuned. X-ray diffraction data in the crystalline state, combined with solution H-1 NMR measurements, show that complexation with trivalent lanthanides, Ln(III), produces the neutral hemi-disklike complexes [Ln(Li)(NO3)(3)] (i = 10, 12), which dimerize to give the rodlike bimetallic complexes [Ln(2)(Li)(2)(NO3)(6)] at lower temperature. The relevant thermodynamic parameters for the latter process depend on the nature of the ligand, the size of the metal ion, and the strength of the intermolecular interactions involved in the condensed phase. These three-dimensional models obtained for the complexes in the crystals and in solution are eventually confronted with small-angle XRD profiles recorded in the intermediate thermotropic liquid crystalline phase, in which the rigidity of the packed polyaromatic cores is maintained, while the alkyl chains are molten. According to the specific geometries and nuclearities of the molecular complexes, three types of mesophases (lamellar, columnar, and cubic) can be induced, which provides a direct correlation between the microscopic arrangements and the macroscopic ordering in lanthanicle-containing metallomesogens.
• Structural, Thermodynamic, and Mesomorphic Consequences of Replacing Nitrates with Trifluoroacetate Counteranions in Ternary Lanthanide Complexes with Hexacatenar Tridentate Ligands
  作者：Homayoun Nozary、Stéphane Torelli、Laure Guénée、Emmanuel Terazzi、Gérald Bernardinelli、Bertrand Donnio、Daniel Guillon、Claude Piguet

  DOI：10.1021/ic052017u

  日期：2006.4.1

  The promesogenic hexacatenar tridentate ligands L3(Cn) (I shape) and L4(Cn) (V shape) react with trivalent lanthanide trifluoroacetates, Ln((CF3CO2)(3), to give either monometallic [Ln(Li-Cn)(CF3CO2)(3)] or trifluoroacetato-bridged bimetallic [Ln(Li-Cn)(CF3CO2)(3)](2) complexes in the solid state, as exemplified by the crystal structures of [Lu(L4(C0))(CF3CO2)(3)-(H2O)], [Lu(L4(C0))(CF3CO2)(3)](2), and [La(L3(C4))(CF3CO2)(3)](2). Although the dimerization process is influenced by the competiting complexation of anions or solvent molecules, the coordination of CF3CO2- instead of NO3- to Ln(III) produces a significant lengthening of the Ln-N(ligand) bond distances. This translates into a considerable decrease of the affinity of the Li-C12 (i = 3, 4) ligands for Ln(CF3CO2)(3) in solution, thus leading to significant dissociation of the [Ln(Li-C12)(CF3CO2)(3)] complexes at millimolar concentrations. The thermal properties of these complexes also suffer from their limited thermodynamic stability, and the thermotropic liquid crystalline phases produced at high temperatures reflect mixtures of different species. However, a hexagonal columnar organization characterizes the main component in the mesophases obtained with [Ln(L3(C12))(CF3CO2)(3)] at high temperature. A tentative interpretation of the small-angle X-ray scaterring (SAXS) profiles suggests that disklike dimers of [Ln(L3(C12))(CF3CO2)(3)](2) are packed along the columnar axes. For [Ln(L4(C12))(CF3CO2)(3)], SAXS profiles are compatible with a lamellar organization in the mesophases originating from the existence of rodlike dimers of [Ln(L4(C12))(CF3CO2)(3)](2) as the major component in the liquid-crystal state.