3,5-bis(dimethyl phosphonatemethyl)benzonitrile | 348621-27-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-bis(dimethyl phosphonatemethyl)benzonitrile
• 英文别名: 3,5-Bis(dimethoxyphosphorylmethyl)benzonitrile
• CAS: 348621-27-2
• 化学式: C₁₃H₁₉NO₆P₂
• 分子量: 347.244
• InChiKey: AGWFHABXTGCIHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  94.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,5-bis(dimethyl phosphonatemethyl)benzonitrile 在 potassium tert-butylate 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 3,5-bis[2'-4(dibuthylaminophenyl)vinyl]benzaldehyde
  参考文献：
  名称：

  带有二丁基氨基外围基团的光活性和电活性类胡萝卜素树状大分子的合成。

  摘要：

  [结构：见文字]。开发了一种新的聚合合成路线，用于制备功能化的和荧光的二苯乙烯类树突，其建立在1,3,5-苯核上并具有二丁基氨基外围。长烷基链已结合在外围氨基部分上以增加最终产物的溶解度。由于存在外围二丁基苯胺部分，通过循环伏安法测量已观察到新的树枝状聚合物的良好供体能力。

  DOI：

  10.1021/ol016083l
• 作为产物：
  描述：

  3,5-二甲基苯腈 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 3,5-bis(dimethyl phosphonatemethyl)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

文献信息

• Synthesis of Photo- and Electroactive Stilbenoid Dendrimers Carrying Dibutylamino Peripheral Groups
  作者：José L. Segura、Rafael Gómez、Nazario Martín、Dirk M. Guldi

  DOI：10.1021/ol016083l

  日期：2001.8.1

  [structure: see text]. A novel convergent synthetic route for the preparation of functionalized and fluorescent stilbenoid dendrons built on the 1,3,5-benzene core and endowed with a periphery of dibutylamino groups has been developed. Long alkyl chains have been incorporated on the peripheral amino moieties to increase the solubility of the final products. Good donor ability of the new dendrimers

  [结构：见文字]。开发了一种新的聚合合成路线，用于制备功能化的和荧光的二苯乙烯类树突，其建立在1,3,5-苯核上并具有二丁基氨基外围。长烷基链已结合在外围氨基部分上以增加最终产物的溶解度。由于存在外围二丁基苯胺部分，通过循环伏安法测量已观察到新的树枝状聚合物的良好供体能力。
• Variation of the energy gap in fullerene-based dendrons: competitive versus sequential energy and electron transfer events
  作者：José L. Segura、Rafael Gómez、Nazario Martín、Chuping Luo、Angela Swartz、Dirk M. Guldi

  DOI：10.1039/b100397f

  日期：——

  Artificial molecular models, based on rigid dendrimeric meta-substituted phenylenevinylene moieties bearing different electron donating groups and the electron acceptor C60, were probed in an effort to gain control over a sequential versus a competitive scenario in energy and electron transfer events.

  基于刚性树枝状聚合物的人工分子模型 间位取代的亚苯基亚乙烯基部分带有不同的 给电子基团和电子受体 C60 试图获得对顺序与顺序的控制 能量和电子转移事件中的竞争场景。
• 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).