3,5-bis[2'-(6-dodecyloxy-2-naphthyl)vinyl]benzaldehyde | 348621-31-8

• 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: 3,5-bis[2'-(6-dodecyloxy-2-naphthyl)vinyl]benzaldehyde
• 英文别名: 3,5-bis[(E)-2-(6-dodecoxynaphthalen-2-yl)ethenyl]benzaldehyde
• CAS: 348621-31-8
• 化学式: C₅₅H₇₀O₃
• 分子量: 779.159
• InChiKey: MIUAZXMSRQUSPA-OGGGYYITSA-N

物化性质

• 熔点：
  101-103 °C(Solvent: Hexane; Dichloromethane)
• 沸点：
  864.3±64.0 °C(predicted)
• 密度：
  1.043±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  19.5
• 重原子数：
  58
• 可旋转键数：
  29
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-bis(dimethyl phosphonatemethyl)benzonitrile 、 3,5-bis[2'-(6-dodecyloxy-2-naphthyl)vinyl]benzaldehyde 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到3,5-bis{2'[3,5-bis[2'-(6-dodecyloxy-2-naphthyl)vinyl]phenylvinyl]}benzonitrile
  参考文献：
  名称：

  Rigid Dendritic Donor−Acceptor Ensembles:  Control over Energy and Electron Transduction

  摘要：

  Several generations of phenylenevinylene dendrons, covalently attached to a C-60 core, have been developed as synthetic model systems with hierarchical, fine-tuned architectures. End-capping of these dendritic spacers with dibutylaniline or dodecyloxynaphthalene, as antennas/electron donors, yielded new donor-bridge-acceptor ensembles in which one, two, or four donors are allocated at the peripheral positions of the well-defined dendrons, while the electron accepting fullerene is placed at the focal point of the dendron. On the basis of our cyclic voltammetry experiments, which disclose a single anodic oxidation and several cathodic reduction processes, we rule out significant, long-range couplings between the fullerene core and the end-standing donors in their ground-state configuration. Photophysical investigations, on the other hand, show that upon photoexcitation an efficient and rapid transfer of singlet excited-state energy (6 x 10(10) to 2.5 N 10(12) s(-1)) controls the reactivity of the initially excited antenna portion. Spectroscopic and kinetic evidence suggests that yet a second contribution, that is, an intramolecular electron-transfer, exists, affording C-60(.-) -dendron(.+) with quantum yields (Phi) as high as 0.76 and lifetimes (tau) that are on the order of hundreds of nanoseconds (220-725 ns). Variation of the energy gap modulates the interplay of these two pathways (i.e., competition or sequence between energy and electron transfer).

  DOI：

  10.1021/ja012694x
• 作为产物：
  描述：

  5-溴间二溴苄 在 potassium tert-butylate 、 二异丁基氢化铝 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 80.0h， 生成 3,5-bis[2'-(6-dodecyloxy-2-naphthyl)vinyl]benzaldehyde
  参考文献：
  名称：

  Rigid Dendritic Donor−Acceptor Ensembles:  Control over Energy and Electron Transduction

  摘要：

  Several generations of phenylenevinylene dendrons, covalently attached to a C-60 core, have been developed as synthetic model systems with hierarchical, fine-tuned architectures. End-capping of these dendritic spacers with dibutylaniline or dodecyloxynaphthalene, as antennas/electron donors, yielded new donor-bridge-acceptor ensembles in which one, two, or four donors are allocated at the peripheral positions of the well-defined dendrons, while the electron accepting fullerene is placed at the focal point of the dendron. On the basis of our cyclic voltammetry experiments, which disclose a single anodic oxidation and several cathodic reduction processes, we rule out significant, long-range couplings between the fullerene core and the end-standing donors in their ground-state configuration. Photophysical investigations, on the other hand, show that upon photoexcitation an efficient and rapid transfer of singlet excited-state energy (6 x 10(10) to 2.5 N 10(12) s(-1)) controls the reactivity of the initially excited antenna portion. Spectroscopic and kinetic evidence suggests that yet a second contribution, that is, an intramolecular electron-transfer, exists, affording C-60(.-) -dendron(.+) with quantum yields (Phi) as high as 0.76 and lifetimes (tau) that are on the order of hundreds of nanoseconds (220-725 ns). Variation of the energy gap modulates the interplay of these two pathways (i.e., competition or sequence between energy and electron transfer).

  DOI：

  10.1021/ja012694x

文献信息

• Rigid Dendritic Donor−Acceptor Ensembles:  Control over Energy and Electron Transduction
  作者：Dirk M. Guldi、Angela Swartz、Chuping Luo、Rafael Gómez、José L. Segura、Nazario Martín

  DOI：10.1021/ja012694x

  日期：2002.9.1

  Several generations of phenylenevinylene dendrons, covalently attached to a C-60 core, have been developed as synthetic model systems with hierarchical, fine-tuned architectures. End-capping of these dendritic spacers with dibutylaniline or dodecyloxynaphthalene, as antennas/electron donors, yielded new donor-bridge-acceptor ensembles in which one, two, or four donors are allocated at the peripheral positions of the well-defined dendrons, while the electron accepting fullerene is placed at the focal point of the dendron. On the basis of our cyclic voltammetry experiments, which disclose a single anodic oxidation and several cathodic reduction processes, we rule out significant, long-range couplings between the fullerene core and the end-standing donors in their ground-state configuration. Photophysical investigations, on the other hand, show that upon photoexcitation an efficient and rapid transfer of singlet excited-state energy (6 x 10(10) to 2.5 N 10(12) s(-1)) controls the reactivity of the initially excited antenna portion. Spectroscopic and kinetic evidence suggests that yet a second contribution, that is, an intramolecular electron-transfer, exists, affording C-60(.-) -dendron(.+) with quantum yields (Phi) as high as 0.76 and lifetimes (tau) that are on the order of hundreds of nanoseconds (220-725 ns). Variation of the energy gap modulates the interplay of these two pathways (i.e., competition or sequence between energy and electron transfer).