N-(2-heptylcarbamoyl-phenyl)-3-methoxy-2-naphthamide | 1340474-98-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(2-heptylcarbamoyl-phenyl)-3-methoxy-2-naphthamide
• 英文别名: N-[2-(heptylcarbamoyl)phenyl]-3-methoxynaphthalene-2-carboxamide
• CAS: 1340474-98-7
• 化学式: C₂₆H₃₀N₂O₃
• 分子量: 418.536
• InChiKey: UODBFCJTXWBZNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻氨基苯甲酸 在 吡啶 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 52.5h， 生成 N-(2-heptylcarbamoyl-phenyl)-3-methoxy-2-naphthamide
  参考文献：
  名称：

  Functional organogel based on a hydroxyl naphthanilide derivative and aggregation induced enhanced fluorescence emission

  摘要：

  A new class of low molecular weight organogelator (LMOG) of hydroxyl naphthanilide moiety was suitably designed and synthesized and it forms gels through noncovalent interactions in hydrocarbon solvents. Self-assembly structure, hydrogen bonding interaction, and photophysical properties of organogelator 3-hydroxy-naphthalene-2-carboxylic acid (2-heptylcarbamoyl-phenyl)-amide (2) have been investigated by field emission scanning electron microscope (FE-SEM), FT-IR, UV-vis absorption and photoluminescence combined with theoretical studies by hybrid density-functional theory (DFT) B3LYP and semi-empirical calculations AM1 with Cl methods. It was found that gelation is completely thermoreversible, and it occurs due to the aggregation of the organogelator resulting in the formation of a fibrous network due to the pi-pi stacking interaction complemented by the presence of both inter- and intra-molecular hydrogen bonding. The self-assembled fibrillar networks in the gels were distinctly evidenced by SEM observations. FT-IR studies confirm that the common driving force for aggregation in the organogels and microsegregation in the mesophase is the occurrence of a tight intermolecular hydrogen bonded network that does not persist in diluted solution. Gelator 2 is very weakly fluorescent in solution, but its intensity is increased by almost 30-32 times in their respective gelled state depending on the nature of the gelling solvents. The aggregation induced emission enhancement is ascribed to the formation of J-aggregation and inhibition of intramolecular rotation in the gel state. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2010.09.014