Trimethyl-[2-[4-[2-[4-[4-[4-[2-[4-(2-trimethylsilylethynyl)-2,5-bis[2-tri(propan-2-yl)silylethynyl]phenyl]ethynyl]-2,5-bis[2-tri(propan-2-yl)silylethynyl]phenyl]buta-1,3-diynyl]-2,5-bis[2-tri(propan-2-yl)silylethynyl]phenyl]ethynyl]-2,5-bis[2-tri(propan-2-yl)silylethynyl]phenyl]ethynyl]silane | 1169835-82-8

• 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: Trimethyl-[2-[4-[2-[4-[4-[4-[2-[4-(2-trimethylsilylethynyl)-2,5-bis[2-tri(propan-2-yl)silylethynyl]phenyl]ethynyl]-2,5-bis[2-tri(propan-2-yl)silylethynyl]phenyl]buta-1,3-diynyl]-2,5-bis[2-tri(propan-2-yl)silylethynyl]phenyl]ethynyl]-2,5-bis[2-tri(propan-2-yl)silylethynyl]phenyl]ethynyl]silane
• CAS: 1169835-82-8
• 化学式: C₁₃₀H₁₉₄Si₁₀
• 分子量: 2037.83
• InChiKey: GDXUDGXHAZLJNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  36.9
• 重原子数：
  140
• 可旋转键数：
  51
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  4-trimethylsilylethynyl-2,5-bis-triisopropylsilylethynyl-iodobenzene 、 1,4-diethynyl-2,5-bis-triisopropylsilylethynylbenzene 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 氧气 、 copper(l) iodide 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 456.25h， 以52%的产率得到Trimethyl-[2-[4-[2-[4-[2-[4-(2-trimethylsilylethynyl)-2,5-bis[2-tri(propan-2-yl)silylethynyl]phenyl]ethynyl]-2,5-bis[2-tri(propan-2-yl)silylethynyl]phenyl]ethynyl]-2,5-bis[2-tri(propan-2-yl)silylethynyl]phenyl]ethynyl]silane
  参考文献：
  名称：

  Synthesis and Properties of Oligo[n]cruciforms: Nanosized Sterically Encumbered Tetraethynylphenyl-Homologated Fluorophores

  摘要：

  A series of nanosized phenylencethynylenes have been prepared which are sterically insulated from the surrounding environment by multiple functionalization with triisopropylsilyl (TIPS) substituents. The phenyleneethynylenes comprise oligo[n]cruciforms 1-4 (n = 3-5) and a dehydrotribenzo[12]annulene 5, the former of which possess para-acyclic and the latter ortho-cyclic electronic conjugation pathways. All compounds were characterized by H-1 and C-13 NMR, IR, and mass spectroscopic techniques. The X-ray crystal structure of 1 confirmed the sterically isolating properties of the TIPS substituents. A comparison of the physical properties of these electronically differing systems revealed that they were all luminescent upon UV irradiation displayed negligible aggregation in dilute solution and that particular members of the series studied were electrochemically active, undergoing facile reversible reductions. The phenyleneethynylenes also exhibited significantly enhanced thermal stability by virtue of the presence of the TIPS substituents. The properties of 1-5 suggest that they are promising building blocks for the construction of materials for novel molecular electronics applications.

  DOI：

  10.1021/jo802797e

文献信息

• Synthesis and Properties of Oligo[<i>n</i>]cruciforms: Nanosized Sterically Encumbered Tetraethynylphenyl-Homologated Fluorophores
  作者：Abdelaziz Al Ouahabi、Paul N. W. Baxter、Jean-Paul Gisselbrecht、André De Cian、Lydia Brelot、Nathalie Kyritsakas-Gruber

  DOI：10.1021/jo802797e

  日期：2009.7.3

  A series of nanosized phenylencethynylenes have been prepared which are sterically insulated from the surrounding environment by multiple functionalization with triisopropylsilyl (TIPS) substituents. The phenyleneethynylenes comprise oligo[n]cruciforms 1-4 (n = 3-5) and a dehydrotribenzo[12]annulene 5, the former of which possess para-acyclic and the latter ortho-cyclic electronic conjugation pathways. All compounds were characterized by H-1 and C-13 NMR, IR, and mass spectroscopic techniques. The X-ray crystal structure of 1 confirmed the sterically isolating properties of the TIPS substituents. A comparison of the physical properties of these electronically differing systems revealed that they were all luminescent upon UV irradiation displayed negligible aggregation in dilute solution and that particular members of the series studied were electrochemically active, undergoing facile reversible reductions. The phenyleneethynylenes also exhibited significantly enhanced thermal stability by virtue of the presence of the TIPS substituents. The properties of 1-5 suggest that they are promising building blocks for the construction of materials for novel molecular electronics applications.