2,6-bis(1-ethyl-6-hydroxybenzimidazol-2-yl)pyridine | 314755-34-5

• 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: 2,6-bis(1-ethyl-6-hydroxybenzimidazol-2-yl)pyridine
• 英文别名: 2,2a(2)-(2,6-Pyridinediyl)bis[1-ethyl-1H-benzimidazol-6-ol]；3-ethyl-2-[6-(1-ethyl-6-hydroxybenzimidazol-2-yl)pyridin-2-yl]benzimidazol-5-ol
• CAS: 314755-34-5
• 化学式: C₂₃H₂₁N₅O₂
• 分子量: 399.452
• InChiKey: VFSDLPMAWLMYOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  30.0
• 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：
  88.99
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  苯甲酸 、 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 [2-[6-(6-Benzoyloxy-1-ethylbenzimidazol-2-yl)pyridin-2-yl]-3-ethylbenzimidazol-5-yl] benzoate
  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

• Metallomesogens with extended bent tridentate receptors: columnar and cubic mesomorphism tuned by the size of the lanthanide metal ionsElectronic supplementary information (ESI) available: experimental procedures and characterization (elemental analyses, NMR, ESI-MS, conductivity) for L3, L3-C4 and L4 and for the complexes [Zn(L1)(NO3)2]·DMF (1), [Zn(Li)(NO3)2]·3H2O (i = 2: 2; i = 4: 3), [Zn(L3)(NO3)2]·H2O (4) and [Ln(L3)(NO3)3] (Ln = Eu, 5; Ln = Dy, 6; Ln = Lu, 7). Tables collecting selected bond distances and bite angles for 1 and L3-C4 and scattering vectors for 5–7. Figures showing intermolecular interactions in 1 and L3-C4, DSC traces for 2, 4 and 6 , birefringent textures for L3 and 7 and a CPK modeling for 7. See http://www.rsc.org/suppdata/dt/b2/b211902a/
  作者：Emmanuel Terazzi、Jean-Marc Bénech、Jean-Pierre Rivera、Gérald Bernardinelli、Bertrand Donnio、Daniel Guillon、Claude Piguet

  DOI：10.1039/b211902a

  日期：2003.2.24

  The increase of the curvature of the interface between the rigid mesogenic core and the aliphatic chains in the hexacatenar tridentate ligand L3 overcomes the considerable expansion brought by the complexation of bulky metallic cores, thus leading to organized cubic mesophases for monometallic zincII and lanthanideIII complexes.

  六链三齿配体L3中刚性介晶核与脂肪链之间界面曲率的增加克服了大块金属核络合带来的相当大的膨胀，从而导致单金属锌II和镧系元素III配合物的有序立方中间相。