4-[2',5'-bis(decyloxy)-4'-ethynylphenylethynyl]-2,5-bis(decyloxy)phenylethynyl-triisopropylsilane | 736179-70-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-[2',5'-bis(decyloxy)-4'-ethynylphenylethynyl]-2,5-bis(decyloxy)phenylethynyl-triisopropylsilane
• 英文别名: 2-[2,5-Didecoxy-4-[2-(2,5-didecoxy-4-ethynylphenyl)ethynyl]phenyl]ethynyl-tri(propan-2-yl)silane；2-[2,5-didecoxy-4-[2-(2,5-didecoxy-4-ethynylphenyl)ethynyl]phenyl]ethynyl-tri(propan-2-yl)silane
• CAS: 736179-70-7
• 化学式: C₆₇H₁₁₀O₄Si
• 分子量: 1007.69
• InChiKey: FYPQLTCEPVGZQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.72
• 重原子数：
  72
• 可旋转键数：
  48
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 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-[2',5'-bis(decyloxy)-4'-ethynylphenylethynyl]-2,5-bis(decyloxy)phenylethynyl-triisopropylsilane 在 四甲基乙二胺 、 copper(l) chloride 作用下， 以 丙酮 为溶剂， 以43%的产率得到1,4-bis(4-((2,5-bis(decyloxy)-4-((triisopropylsilyl)ethynyl)phenyl)ethynyl)-2,5-bis(decyloxy)phenyl)buta-1,3-diyne
  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：

  1-碘癸烷 在 bis-triphenylphosphine-palladium(II) chloride 氢氧化钾 、 copper(l) iodide 、 TEA 、 mercury(II) diacetate 、 碘 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 4-[2',5'-bis(decyloxy)-4'-ethynylphenylethynyl]-2,5-bis(decyloxy)phenylethynyl-triisopropylsilane
  参考文献：
  名称：

  多个[60]富勒烯-寡聚（对亚苯基乙炔基）杂化物的合成，光谱和非线性光学性质。

  摘要：

  通过一种新开发的原位乙炔化方法，合成了一系列多个[60]富勒烯封端的低聚（对亚苯基乙炔基）（OPE）杂化化合物。通过1D和2D NMR光谱分析表征了高度不饱和的富碳C（60）和OPE支架的结构和磁屏蔽性能。[60]富勒烯与OPE骨架之间的电子相互作用通过UV / Vis光谱和循环伏安法（CV）实验进行了研究。我们的研究清楚地表明，尽管多个[60]富勒烯基团通过pi共轭OPE框架连接，但它们在基态下呈现出微小的电子相互作用，并且[60]富勒烯笼的电子行为仅受OPE主链影响通过适度的感应效应。有趣的是，确定了相对于其OPE前驱体的多富勒烯-OPE杂化体31的较大的三阶非线性光学（NLO）响应（γ）和增强的双光子吸收（TPA）截面（sigma（（2）））。克尔效应（DOKE）实验。这种增强的NLO性能大概是由于在激发态中发生过共轭和/或电荷转移效应。另外，观察到了OPE五聚体12的相对强的激发态

  DOI：

  10.1002/chem.200401198

文献信息

• Facile Synthesis of Multifullerene-OPE Hybrids via in Situ Ethynylation
  作者：Yasuhiro Shirai、Yuming Zhao、Long Cheng、James M. Tour

  DOI：10.1021/ol049447t

  日期：2004.6.1

  A series of fullerene-terminated oligo(phenylene ethynylene)s (OPEs) (1a-d and 2) have been synthesized and further characterized by cyclic voltammetry (CV) and UV-vis spectroscopy. The key step in the syntheses is an effective one-pot reaction that allows the attachment of C-50 to multiple terminal alkynes.
• Synthesis of a Porphyrin-Fullerene Pinwheel
  作者：Takashi Sasaki、Andrew J. Osgood、J. L. Kiappes、Kevin F. Kelly、James M. Tour

  DOI：10.1021/ol7029917

  日期：2008.4.1

  We disclose the synthesis of a porphyrin-fullerene pinwheel that was subsequently observed by scanning tunneling microscopy. The molecule was designed to further our understanding of fullerene-surface interactions, directional control, and surface-rolling versus pivoting capabilities of this class of nanomachines. The inner porphyrin provides the square planar configuration that might lead to realization of the pinwheel spiraling motion on surfaces.
• Synthesis, electronic, and photophysical properties of cruciform OPE/OPV hybrid oligomer bridged bisfullerene triads
  作者：Ningzhang Zhou、Li Wang、David W. Thompson、Yuming Zhao

  DOI：10.1016/j.tetlet.2007.03.092

  日期：2007.5

  A series of cruciform-shaped phenyleneethynylene and phenylenevinylene hybrid oligomers was prepared via a sequence of Sonogashira reactions. Using an in situ ethynylation protocol, these oligomers were end-functionalized with bis(fullerenyl) groups at the termini of the oligomers. Spectroscopic and electrochemical properties of these novel bisfullerene triads were studied in detail by UV-vis, fluorescence, and cyclic voltammetric analyses, and the results of these investigations are reported. (C) 2007 Elsevier Ltd. All rights reserved.
• Synthesis, Spectroscopic and Nonlinear Optical Properties of Multiple [60]Fullerene-Oligo(p-phenylene ethynylene) Hybrids
  作者：Yuming Zhao、Yasuhiro Shirai、Aaron D. Slepkov、Long Cheng、Lawrence B. Alemany、Takashi Sasaki、Frank A. Hegmann、James M. Tour

  DOI：10.1002/chem.200401198

  日期：2005.6.6

  spectroscopic and cyclic voltammetry (CV) experiments. Our studies clearly show that although the multiple [60]fullerene groups are connected via pi-conjugated OPE frameworks, they present diminutive electronic interactions in the ground state, and the electronic behavior of the [60]fullerene cages are only affected by the OPE backbones through modest inductive effects. Interestingly, sizable third-order

  通过一种新开发的原位乙炔化方法，合成了一系列多个[60]富勒烯封端的低聚（对亚苯基乙炔基）（OPE）杂化化合物。通过1D和2D NMR光谱分析表征了高度不饱和的富碳C（60）和OPE支架的结构和磁屏蔽性能。[60]富勒烯与OPE骨架之间的电子相互作用通过UV / Vis光谱和循环伏安法（CV）实验进行了研究。我们的研究清楚地表明，尽管多个[60]富勒烯基团通过pi共轭OPE框架连接，但它们在基态下呈现出微小的电子相互作用，并且[60]富勒烯笼的电子行为仅受OPE主链影响通过适度的感应效应。有趣的是，确定了相对于其OPE前驱体的多富勒烯-OPE杂化体31的较大的三阶非线性光学（NLO）响应（γ）和增强的双光子吸收（TPA）截面（sigma（（2）））。克尔效应（DOKE）实验。这种增强的NLO性能大概是由于在激发态中发生过共轭和/或电荷转移效应。另外，观察到了OPE五聚体12的相对强的激发态
• 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.