(4,4'-(5-((trimethylsilyl)buta-1,3-diynyl)-1,3-phenylene)bis(ethyne-2,1-diyl)bis(2,5-bis(decyloxy)-4,1-phenylene))bis(ethyne-2,1-diyl)bis(triisopropylsilane) | 1211509-54-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (4,4'-(5-((trimethylsilyl)buta-1,3-diynyl)-1,3-phenylene)bis(ethyne-2,1-diyl)bis(2,5-bis(decyloxy)-4,1-phenylene))bis(ethyne-2,1-diyl)bis(triisopropylsilane)
• 英文别名: 4-[3,5-Bis[2-[2,5-didecoxy-4-[2-tri(propan-2-yl)silylethynyl]phenyl]ethynyl]phenyl]buta-1,3-diynyl-trimethylsilane
• CAS: 1211509-54-4
• 化学式: C₉₁H₁₄₂O₄Si₃
• 分子量: 1384.38
• InChiKey: IWPOXNDLGCBPPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  26.94
• 重原子数：
  98
• 可旋转键数：
  57
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4,4'-(5-((trimethylsilyl)buta-1,3-diynyl)-1,3-phenylene)bis(ethyne-2,1-diyl)bis(2,5-bis(decyloxy)-4,1-phenylene))bis(ethyne-2,1-diyl)bis(triisopropylsilane) 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以81%的产率得到(4,4'-(5-(buta-1,3-diynyl)-1,3-phenylene)bis(ethyne-2,1-diyl)-bis(2,5-bis(decyloxy)-4,1-phenylene))bis(ethyne-2,1-diyl)bis(triisopropylsilane)
  参考文献：
  名称：

  Conjugated Oligoyne-Bridged [60]Fullerene Molecular Dumbbells: Syntheses and Thermal and Morphological Properties

  摘要：

  A series of linear and star-shaped pi-conjugated oligomer hybrids (2-5) composed of an oligoyne core, ranging from 1,3-butadiyne to 1,3,5.7,9,11-dodecahexayne, and fullerenyl end-capping groups has been synthesized and studied. The molecular structures of these fullerene-oligoyne hybrids were assembled through three key reactions. Pd-catalyzed cross-coupling, Cu-catalyzed oxidative homocoupling, and an in situ alkynylation reaction on [60]fullerene. The properties of these compound were investigated by UV-vis spectroscopy, differential scanning calorimetry (DSC), and atomic force microscopy (AFM) with the purpose of understanding the thermal reactivity arising from the oliogyne moieties as well as the morphological properties on surface. Our study shows that these fullerene-oliogyne hybrids tend to aggregate in different morphologies, including nanospheres, nanoflakes, and continuous thin films, while the morphological properties appear to be subject to the influence of molecular factors such as oligomer chain length, solubilizing alkylphenyl groups, and the thermal reactivity of the oligoyne unit. The correlation between molecular property and interfacial aggregation behavior evinced by these fullerene-oligoyne hybrids suggests a viable approach to exert bottom-up control over the structures and properties of fullerene based nanomaterials.

  DOI：

  10.1021/jo9021748
• 作为产物：
  描述：

  (4,4'-(5-ethynyl-1,3-phenylene)bis(ethyne-2,1-diyl)bis(2,5-bis(decyloxy)-4,1-phenylene))bis(ethyne-2,1-diyl)bis(triisopropylsilane) 、 三甲基乙炔基硅 在 四甲基乙二胺 、 copper(l) chloride 作用下， 以 丙酮 为溶剂， 反应 40.0h， 以89%的产率得到(4,4'-(5-((trimethylsilyl)buta-1,3-diynyl)-1,3-phenylene)bis(ethyne-2,1-diyl)bis(2,5-bis(decyloxy)-4,1-phenylene))bis(ethyne-2,1-diyl)bis(triisopropylsilane)
  参考文献：
  名称：

  Conjugated Oligoyne-Bridged [60]Fullerene Molecular Dumbbells: Syntheses and Thermal and Morphological Properties

  摘要：

  A series of linear and star-shaped pi-conjugated oligomer hybrids (2-5) composed of an oligoyne core, ranging from 1,3-butadiyne to 1,3,5.7,9,11-dodecahexayne, and fullerenyl end-capping groups has been synthesized and studied. The molecular structures of these fullerene-oligoyne hybrids were assembled through three key reactions. Pd-catalyzed cross-coupling, Cu-catalyzed oxidative homocoupling, and an in situ alkynylation reaction on [60]fullerene. The properties of these compound were investigated by UV-vis spectroscopy, differential scanning calorimetry (DSC), and atomic force microscopy (AFM) with the purpose of understanding the thermal reactivity arising from the oliogyne moieties as well as the morphological properties on surface. Our study shows that these fullerene-oliogyne hybrids tend to aggregate in different morphologies, including nanospheres, nanoflakes, and continuous thin films, while the morphological properties appear to be subject to the influence of molecular factors such as oligomer chain length, solubilizing alkylphenyl groups, and the thermal reactivity of the oligoyne unit. The correlation between molecular property and interfacial aggregation behavior evinced by these fullerene-oligoyne hybrids suggests a viable approach to exert bottom-up control over the structures and properties of fullerene based nanomaterials.

  DOI：

  10.1021/jo9021748

文献信息

• Conjugated Oligoyne-Bridged [60]Fullerene Molecular Dumbbells: Syntheses and Thermal and Morphological Properties
  作者：Ningzhang Zhou、Yuming Zhao

  DOI：10.1021/jo9021748

  日期：2010.3.5

  A series of linear and star-shaped pi-conjugated oligomer hybrids (2-5) composed of an oligoyne core, ranging from 1,3-butadiyne to 1,3,5.7,9,11-dodecahexayne, and fullerenyl end-capping groups has been synthesized and studied. The molecular structures of these fullerene-oligoyne hybrids were assembled through three key reactions. Pd-catalyzed cross-coupling, Cu-catalyzed oxidative homocoupling, and an in situ alkynylation reaction on [60]fullerene. The properties of these compound were investigated by UV-vis spectroscopy, differential scanning calorimetry (DSC), and atomic force microscopy (AFM) with the purpose of understanding the thermal reactivity arising from the oliogyne moieties as well as the morphological properties on surface. Our study shows that these fullerene-oliogyne hybrids tend to aggregate in different morphologies, including nanospheres, nanoflakes, and continuous thin films, while the morphological properties appear to be subject to the influence of molecular factors such as oligomer chain length, solubilizing alkylphenyl groups, and the thermal reactivity of the oligoyne unit. The correlation between molecular property and interfacial aggregation behavior evinced by these fullerene-oligoyne hybrids suggests a viable approach to exert bottom-up control over the structures and properties of fullerene based nanomaterials.