2,5-bis[(triisopropylsilyl)ethynyl]-1,4-bis[(trimethylsilyl)ethynyl]benzene | 834856-06-3

• 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: 2,5-bis[(triisopropylsilyl)ethynyl]-1,4-bis[(trimethylsilyl)ethynyl]benzene
• 英文别名: 1,4-bis(triisopropylsilylacetylene)-2,5-bis(trimethylsilylacetylene)benzene；1,4-bis-trimethylsilylethynyl-2,5-bis-triisopropylsilylethynylbenzene；Trimethyl-[2-[4-(2-trimethylsilylethynyl)-2,5-bis[2-tri(propan-2-yl)silylethynyl]phenyl]ethynyl]silane
• CAS: 834856-06-3
• 化学式: C₃₈H₆₂Si₄
• 分子量: 631.252
• InChiKey: JOLLWJZRUXYNDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.28
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,5-bis[(triisopropylsilyl)ethynyl]-1,4-bis[(trimethylsilyl)ethynyl]benzene 在 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 1,4-diethynyl-2,5-bis-triisopropylsilylethynylbenzene
  参考文献：
  名称：

  供体-受体四（苯乙炔基）苯的合成及光学性质

  摘要：

  描述了一系列供体-受体取代的 1,2,4,5-四（苯基乙炔基）苯的简单有效合成。构建的分子表现出有趣的光学特性。初步研究表明，四炔有望作为非线性光学 (NLO) 材料。

  DOI：

  10.1055/s-2003-43372
• 作为产物：
  描述：

  1,4-二溴-2,5-二碘苯 在 bis-triphenylphosphine-palladium(II) chloride 、 四(三苯基膦)钯 copper(l) iodide 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 2,5-bis[(triisopropylsilyl)ethynyl]-1,4-bis[(trimethylsilyl)ethynyl]benzene
  参考文献：
  名称：

  供体-受体四（苯乙炔基）苯的合成及光学性质

  摘要：

  描述了一系列供体-受体取代的 1,2,4,5-四（苯基乙炔基）苯的简单有效合成。构建的分子表现出有趣的光学特性。初步研究表明，四炔有望作为非线性光学 (NLO) 材料。

  DOI：

  10.1055/s-2003-43372

文献信息

• Synthetic Routes toward Carborane-Wheeled Nanocars
  作者：Jean-François Morin、Takashi Sasaki、Yasuhiro Shirai、Jason M. Guerrero、James M. Tour

  DOI：10.1021/jo701400t

  日期：2007.12.1

  [GRAPHICS]A new set of aryleneethynylene derivatives bearing three, four, and six p-carboranes as potential wheels attached to a semirigid chassis have been designed and synthesized. These molecules are expected to move in predetermined patterns on atomically smooth surfaces, depending on their specific configuration.
• Structure−Property Relationships of Donor/Acceptor-Functionalized Tetrakis(phenylethynyl)benzenes and Bis(dehydrobenzoannuleno)benzenes
  作者：Jeremiah A. Marsden、Jeremie J. Miller、Laura D. Shirtcliff、Michael M. Haley

  DOI：10.1021/ja044175a

  日期：2005.3.1

  A series of tetrakis(phenylethynyl)benzenes and bis(dehydrobenzoannuleno)benzenes have been synthesized containing tetra-substitutions of neutral, donor, and mixed donor/acceptor groups. To ascertain the importance of substitutional and structural differences of the phenylacetylenes, the optical absorption and emission properties of each series were examined. Conjugation effectiveness, electron density, planarity, and geometry of charge-transfer pathways were found to have a pronounced effect on the overall optical and material properties. Considerable self-association behavior due to face-to-face stacking in solution was observed for donor/acceptor-functionalized macrocycles and was quantified by concentration-dependent H-1 NMR measurements. A solvent-dependent polymerization of one macrocycle regioisomer was observed and characterized. To provide further insight into the energy levels and electronic transitions present, computational studies of each system were performed.
• 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.