2,4-diamino-6-[(E,E,E)-4-<4-{4-(3,4,5-tridodecyloxystyryl)-2,5-bis[(S)-2-methylbutoxy]styryl}-2,5-bis[(S)-2-methylbutoxy]styryl>]phenyl-s-triazine | 328249-47-4

• 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: 2,4-diamino-6-[(E,E,E)-4-<4-{4-(3,4,5-tridodecyloxystyryl)-2,5-bis[(S)-2-methylbutoxy]styryl}-2,5-bis[(S)-2-methylbutoxy]styryl>]phenyl-s-triazine
• 英文别名: 2,4-diamino-6-{[(E,E,E)-4-{4-{4-(3,4,5-trisdodecyloxystyryl)-2,5-bis[(S)-2-methylbutoxy]styryl}-2,5-bis[(S)-2-methylbutoxy]styryl}]phenyl}-s-triazine；S-OPV4T；6-[4-[(E)-2-[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]phenyl]ethenyl]phenyl]-1H-1,3,5-triazine-2,4-diimine
• CAS: 328249-47-4
• 化学式: C₈₉H₁₃₉N₅O₇
• 分子量: 1391.11
• InChiKey: YVZDXLHBZYFUBJ-CYXNMSMGSA-N

物化性质

• 沸点：
  1206.9±75.0 °C(predicted)
• 密度：
  1.017±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  31
• 重原子数：
  101
• 可旋转键数：
  59
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  异氰酸正丁酯 、 2,4-diamino-6-[(E,E,E)-4-<4-{4-(3,4,5-tridodecyloxystyryl)-2,5-bis[(S)-2-methylbutoxy]styryl}-2,5-bis[(S)-2-methylbutoxy]styryl>]phenyl-s-triazine 在 吡啶 作用下， 反应 8.0h， 以58%的产率得到2-amino-4-butylureido-6-[(E,E,E)-4-<4-{4-(3,4,5-tridodecyloxystyryl)-2,5-bis[(S)-2-methylbutoxy]styryl}-2,5-bis[(S)-2-methylbutoxy]styryl>]phenyl-s-triazine
  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
• 作为产物：
  描述：

  二聚氰胺 、 (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 氢氧化钾 作用下， 以 乙二醇甲醚 为溶剂， 生成 2,4-diamino-6-[(E,E,E)-4-<4-{4-(3,4,5-tridodecyloxystyryl)-2,5-bis[(S)-2-methylbutoxy]styryl}-2,5-bis[(S)-2-methylbutoxy]styryl>]phenyl-s-triazine
  参考文献：
  名称：

  Transfer of π-Conjugated Columnar Stacks from Solution to Surfaces

  摘要：

  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.

  DOI：

  10.1021/ja0383118

文献信息

• Hydrogen-Bonded Oligo(p-phenylenevinylene) Functionalized with Perylene Bisimide: Self-Assembly and Energy Transfer
  作者：Jian Zhang、Freek J. M. Hoeben、Maarten J. Pouderoijen、Albertus P. H. J. Schenning、E. W. Meijer、Frans C. De Schryver、Steven De Feyter

  DOI：10.1002/chem.200600651

  日期：2006.12.4

  different electronic properties of the oligo(p-phenylenevinylene) and perylene bisimide moieties. In dodecane, the molecule self-assembles into H-type aggregates that are still soluble as a result of the hydrophobic shell formed by the dodecyloxy wedges. The donor-acceptor molecule is characterized by efficient energy transfer from the photoexcited OPV to the perylene bisimide. Mixed assemblies with analogous

  我们描述了合成，超分子在表面和溶液中的有序排列，以及OPV4UT-PERY（具有共价连接的bi双酰亚胺部分的低聚（对亚苯基亚乙烯基）（OPV））的光物理特征。在氯仿中，分子通过脲基-s-三嗪阵列的四重氢键形成二聚体。这通过扫描隧道显微镜（STM）研究得到支持，该研究揭示了在液体（1,2,4-三氯苯）/固体（石墨）界面处的二聚体形成。此外，依赖于偏压的STM成像中的对比度反转提供了有关低聚（对亚苯基亚乙烯基）和per双酰亚胺部分的有序性和不同电子性质的信息。在十二烷中，由于十二烷氧基楔形分子形成的疏水壳，分子自组装成H型聚集体，这些聚集体仍然可溶。供体-受体分子的特征在于从光激发的OPV到to二酰亚胺的有效能量转移。已经在十二烷溶液中制备了具有类似OPV的，缺少per双酰亚胺单元的混合组件，并且已经通过荧光光谱研究了向结合的per双酰亚胺的能量转移。
• On the transfer of cooperative self-assembled π-conjugated fibrils to a gold substrate
  作者：Martin Wolffs、Mantas Malisauskas、Inge De Cat、Željko Tomović、Jeroen van Herrikhuyzen、Christianus M. A. Leenders、Evan J. Spadafora、Benjamin Grévin、Steven De Feyter、E. W. Meijer、Albertus P. H. J. Schenning、Philippe Leclère

  DOI：10.1039/c1cc12799c

  日期：——

  The transfer of the cooperative self-assembled fibrils to a gold substrate has been studied by means of scanning probe microscopy techniques revealing the crucial role of the early formation of a monolayer.

  通过扫描探针显微镜技术，研究人员研究了将自组装纤维转移到金基底上的过程，揭示了单层早期形成的关键作用。
• 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.
• 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.