(E,E,E)-4-[4-{4-(3,4,5-tridodecyloxystyryl)-2,5-bis[(S)-2-methylbutoxy]styryl}-2,5-bis[(S)-2-methylbutoxy]styryl]phenylnitrile | 328249-46-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E,E,E)-4-[4-{4-(3,4,5-tridodecyloxystyryl)-2,5-bis[(S)-2-methylbutoxy]styryl}-2,5-bis[(S)-2-methylbutoxy]styryl]phenylnitrile
• CAS: 328249-46-3
• 化学式: C₈₇H₁₃₅NO₇
• 分子量: 1307.03
• InChiKey: MNXKJZPOUILBJV-FIQCIWHWSA-N

物化性质

• 沸点：
  1126.0±65.0 °C(predicted)
• 密度：
  1.01±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  26.67
• 重原子数：
  95.0
• 可旋转键数：
  58.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  88.4
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (E,E,E)-4-[4-{4-(3,4,5-tridodecyloxystyryl)-2,5-bis[(S)-2-methylbutoxy]styryl}-2,5-bis[(S)-2-methylbutoxy]styryl]phenylnitrile 在 二异丁基氢化铝 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 1.0h， 以66%的产率得到(E,E,E)-4-[4-{4-(3,4,5-tridodecyloxystyryl)-2,5-bis[(S)-2-methylbutoxy]styryl}-2,5-bis[(S)-2-methylbutoxy]styryl]benzaldehyde
  参考文献：
  名称：

  超分子结构对手性低聚（对亚苯基亚乙烯基）卟啉组装体能量传递特性的影响

  摘要：

  介绍了对包含所有反式亚乙烯基（亲水性或亲脂性）或酰胺键（亲脂性）的低聚（对亚苯基亚乙烯基）（OPV）附加卟啉的比较研究。在有机溶剂中获得的超分子排列类型证明强烈依赖于共价连接的性质。在所有反式亚乙烯基键的情况下，获得J型分子间堆积并且组装仅具有中等稳定性。相反，从酰胺连接系统获得的超分子结构显示出 H 型堆叠排列，由于沿堆叠方向的分子间氢键，从而使堆叠的构建块有利地互锁，从而增强了稳定性和手性。有趣的是，观察到的稳定性和组织性差异通过监测两种类型组件的顺序能量转移过程定性地说明。在两个系统中，从 OPV（供体）到相应卟啉核心的有效分子内能量转移之后是从锌卟啉（供体）到游离碱卟啉（受体）的能量转移。然而，酰胺连接系统改进的分子间组织提高了沿堆叠方向的能量转移效率。此外，水溶性 (OPV) 附加卟啉系统在水性环境中形成高度稳定的组件。然而，沿堆叠方向较差的能量传输效率表明这些组件相对缺乏组织。在两个系统中，从

  DOI：

  10.1021/ja072548c
• 作为产物：
  描述：

  3,4,5-三(十二烷氧基)苯甲醛 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 73.25h， 生成 (E,E,E)-4-[4-{4-(3,4,5-tridodecyloxystyryl)-2,5-bis[(S)-2-methylbutoxy]styryl}-2,5-bis[(S)-2-methylbutoxy]styryl]phenylnitrile
  参考文献：
  名称：

  Hierarchical Order in Supramolecular Assemblies of Hydrogen-Bonded Oligo(p-phenylene vinylene)s

  摘要：

  Mono- and bifunctional oligo(p-phenylene vinylene)s (OPVs) functionalized with ureido-s-triazine units have been synthesized and fully characterized. In chloroform monofunctional OPV derivatives dimerize with a dimerization constant of K-dim = (2.1 +/- 0.3) x 10(4) L/mol, while bifunctional OPV derivatives are present as random coil polymers in this solvent. In more apolar solvents such as dodecane, the hydrogen-bonded dimers of the monofunctional OPV derivative aggregate in chiral stacks, as can be concluded from UV/vis, fluorescence and CD spectroscopy. Temperature-dependent measurements show a first-order transition at 53 +/- 3 degreesC from the aggregated state to the molecularly dissolved phase. The bifunctional derivative also aggregates in dodecane; however, based on CD measurements, these aggregates are less: organized. This behavior is presumably the outcome of a competition between favorable pi-pi interactions and restricted conformational freedom, due to the hexyl spacer, which results in a frustrated supramolecular polymeric stack. The length of these polymers as well as the chiral order in the assemblies can be controlled by the addition of monofunctional OPV derivatives.

  DOI：

  10.1021/ja0033180

文献信息

• Quadruple hydrogen bonded oligo(p-phenylene vinylene) dimers
  作者：Abdelkrim El-ghayoury、Emiel Peeters、Albertus P. H. J. Schenning、E. W. Meijer

  DOI：10.1039/b005903j

  日期：——

  Direct self-assembly of π-conjugated oligomers via self-complementary quadruple hydrogen bonding is achieved and the first steps towards supramolecular polymers with functional side chains are described.

  通过自互补四重氢键实现了π-共轭低聚物的直接自组装，并描述了朝向具有功能侧链的超分子聚合物的第一步。
• Transfer of π-Conjugated Columnar Stacks from Solution to Surfaces
  作者：Pascal Jonkheijm、Freek J. M. Hoeben、Ralf Kleppinger、Jeroen van Herrikhuyzen、Albertus P. H. J. Schenning、E. W. Meijer

  DOI：10.1021/ja0383118

  日期：2003.12.1

  Three hydrogen-bonded oligo(p-phenylenevinylene)s, OPV3, OPV4, and OPV5, that differ in conjugation length have been synthesized and fully characterized. All three compounds contain chiral side chains, long aliphatic chains, and a ureido-s-triazine hydrogen bonding unit. H-1 NMR and photophysical measurements show that the OPV oligomers grow hierarchically in an apolar solvent; initially, dimers are formed by hydrogen bonds that subsequently develop into stacks by pi-pi interactions of the phenylenevinylene backbone with induced helicity via the chiral side chains. SANS measurements show that rigid cylindrical objects are formed. Stacks of OPV4 have a persistence length of 150 nm and a diameter of 6 nm. OPV3 shows rigid columnar domains of 60 nm with a diameter of 5 nm. Temperature and concentration variable measurements show that the stability of the stacks increases with the conjugation length as a result of more favorable pi-pi interactions. The transfer of the single cylinders from solution to a solid support as isolated objects is only possible when specific concentrations and specific solid supports are used as investigated by AFM. At higher concentrations, an intertwined network is formed, while, at low concentration, ill-defined globular objects are observed. Only in the case of inert substrates (graphite and silicium oxide) single fibers are visible. In the case of the repulsive surfaces (mica and glass), clustering of the stacks occurs, while, at attractive surfaces (gold), the stacks are destroyed.