(E,E)-4-{4-(3,4,5-tridodecyloxystyryl)-2,5-bis[(S)-2-methylbutoxy]styryl}-2,5-bis[(S)-2-methylbutoxy]benzaldehyde | 328249-45-2

• 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)-4-{4-(3,4,5-tridodecyloxystyryl)-2,5-bis[(S)-2-methylbutoxy]styryl}-2,5-bis[(S)-2-methylbutoxy]benzaldehyde
• 英文别名: 4-[(E)-2-[2,5-bis[(2S)-2-methylbutoxy]-4-[(E)-2-(3,4,5-tridodecoxyphenyl)ethenyl]phenyl]ethenyl]-2,5-bis[(2S)-2-methylbutoxy]benzaldehyde
• CAS: 328249-45-2
• 化学式: C₇₉H₁₃₀O₈
• 分子量: 1207.9
• InChiKey: FICKOSGJSFKATB-YYKBAHKDSA-N

物化性质

• 沸点：
  1061.4±65.0 °C(Predicted)
• 密度：
  0.969±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  29.2
• 重原子数：
  87
• 可旋转键数：
  57
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (E,E)-4-{4-(3,4,5-tridodecyloxystyryl)-2,5-bis[(S)-2-methylbutoxy]styryl}-2,5-bis[(S)-2-methylbutoxy]benzaldehyde 在 lithium aluminium tetrahydride 、 potassium tert-butylate 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 1,2,3-tris(dodecyloxy)-5-((E)-4-((E)-4-((E)-4-(isocyanatomethyl)styryl)-2,5-bis((S)-2-methylbutoxy)styryl)-2,5-bis((S)-2-methylbutoxy)styryl)benzene
  参考文献：
  名称：

  Quadruple hydrogen bonded oligo(p-phenylene vinylene) dimers

  摘要：

  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。

  DOI：

  10.1039/b005903j
• 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 1.0h， 生成 (E,E)-4-{4-(3,4,5-tridodecyloxystyryl)-2,5-bis[(S)-2-methylbutoxy]styryl}-2,5-bis[(S)-2-methylbutoxy]benzaldehyde
  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

• Supramolecular organisation of oligo(p-phenylenevinylene) at the air–water interface and in water
  作者：Pascal Jonkheijm、Michel Fransen、Albertus P. H. J. Schenning、E. W. Meijer

  DOI：10.1039/b103966k

  日期：——

  aggregate in chiral stacks, as can be concluded from UV–vis, fluorescence and CD spectroscopy. Temperature dependent measurements showed for OPV1 a transition at 50 °C from a chiral aggregated state to disordered aggregates. In the case of bolaamphiphilic OPV2, the transition at 55 °C between those states is a less cooperative process. The chiral order in the assemblies of the bolaamphiphiles can be influenced

  合成了两种新颖的手性（博拉）两亲性低聚物（对苯撑亚乙烯基）（OPV）并对其进行了全面表征。在一侧用亲水性三[四（环氧乙烷）]苯楔和在另一侧用疏水性三（烷氧基）苯楔装饰疏水性OPV主链，得到两亲性OPV1。在双亲性亲油OPV2中，两个亲水的三[四（环氧乙烷）]苯楔形分子连接在OPV主链的两端。已经在空气-水界面和水中对两亲物的组织进行了研究。OPV1的Langmuir单层膜表明，这些两亲物在空气-水界面处垂直定向。对于OPV2，OPV单元平放在子相上，亲水性乙二醇楔形物指向水相。在氯仿中，OPV衍生物以分子溶解形式存在。在水中，两亲OPV衍生物聚集在手性堆栈中，这可以从UV-vis，荧光和CD光谱学得出结论。温度相关的测量结果显示，OPV1在50°C时从手性聚集态过渡到无序聚集体。就嗜两性OPV2而言，这些状态之间在55°C的转变是一个较不协调的过程。盐的添加会影响双亲性亲脂分子装配体中的手性顺序。
• 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.
• Fractal-like Self-Assembly of Oligo(<i>p</i>-phenylene vinylene) Capped Gold Nanoparticles
  作者：Jeroen van Herrikhuyzen、René A. J. Janssen、E. W. Meijer、Stefan C. J. Meskers、Albertus P. H. J. Schenning

  DOI：10.1021/ja056504k

  日期：2006.1.1

  Reversible interparticle self-organization is reported for gold nanoparticles functionalized with an oligo(p-phenylene vinylene) moiety in butanol. The aggregates show a clear melting temperature at 80 degrees C, and atomic force microscopy and transmission electron microscopy indicate a fractal-like organization of the particles.
• 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。
• Hierarchical Order in Supramolecular Assemblies of Hydrogen-Bonded Oligo(<i>p</i>-phenylene vinylene)s
  作者：Albertus P. H. J. Schenning、Pascal Jonkheijm、Emiel Peeters、E. W. Meijer

  DOI：10.1021/ja0033180

  日期：2001.1.1

  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.