1-dodecyl-2-hydroxy-4-methyl-6-oxo-1,6-dihydropyridine-3-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-dodecyl-2-hydroxy-4-methyl-6-oxo-1,6-dihydropyridine-3-carbonitrile
• 英文别名: 1-Dodecyl-2-hydroxy-4-methyl-6-oxopyridine-3-carbonitrile
• 化学式: C₁₉H₃₀N₂O₂
• 分子量: 318.459
• InChiKey: RMTHFCKIYSHCAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  64.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-dodecyl-2-hydroxy-4-methyl-6-oxo-1,6-dihydropyridine-3-carbonitrile 、 1-(3-(4-(dodecyloxy)-6-(methoxycarbonyl)picolinamido)propyl)-4-methylpyridin-1-ium bromide 、 N,N'-二苯甲脒 在 乙酸酐 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.5h， 以75%的产率得到
  参考文献：
  名称：

  Stepwise Folding and Self-Assembly of a Merocyanine Folda-Pentamer

  摘要：

  Here we report a synthetic protocol toward a merocyanine (MC) pentamer 1 which represents the first merocyanine oligomer longer than a dimer. By continuously decreasing the solvent polarity, we demonstrate the stepwise folding from partially folded monomeric and dimeric MC subunits (in chloroform) up to the full pentamer jr-stack (in 75% methylcyclohexane/25% chloroform) and a subsequent self-assembly of pentamer 1 into larger aggregates (in 80% methylcyclohexane/20% chloroform). This hierarchical structure formation process became possible due to the predominant dipole-dipole interactions among MC dyes that allowed for a precise modulation of the energy landscape by the solvent polarity. This unprecedented stepwise control of dye assembly via hierarchical dipole-dipole interactions opens the door for a more precise control of dye-dye interactions in artificial multichromophoric ensembles.

  DOI：

  10.1021/jacs.9b12599

文献信息

• Stepwise Folding and Self-Assembly of a Merocyanine Folda-Pentamer
  作者：Xiaobo Hu、Joachim O. Lindner、Frank Würthner

  DOI：10.1021/jacs.9b12599

  日期：2020.2.19

  Here we report a synthetic protocol toward a merocyanine (MC) pentamer 1 which represents the first merocyanine oligomer longer than a dimer. By continuously decreasing the solvent polarity, we demonstrate the stepwise folding from partially folded monomeric and dimeric MC subunits (in chloroform) up to the full pentamer jr-stack (in 75% methylcyclohexane/25% chloroform) and a subsequent self-assembly of pentamer 1 into larger aggregates (in 80% methylcyclohexane/20% chloroform). This hierarchical structure formation process became possible due to the predominant dipole-dipole interactions among MC dyes that allowed for a precise modulation of the energy landscape by the solvent polarity. This unprecedented stepwise control of dye assembly via hierarchical dipole-dipole interactions opens the door for a more precise control of dye-dye interactions in artificial multichromophoric ensembles.