[4-(4-bromophenylethynyl)phenylethynyl]triisopropylsilane | 695152-69-3

• 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: [4-(4-bromophenylethynyl)phenylethynyl]triisopropylsilane
• 英文别名: 2-[4-[2-(4-Bromophenyl)ethynyl]phenyl]ethynyl-tri(propan-2-yl)silane；2-[4-[2-(4-bromophenyl)ethynyl]phenyl]ethynyl-tri(propan-2-yl)silane
• CAS: 695152-69-3
• 化学式: C₂₅H₂₉BrSi
• 分子量: 437.495
• InChiKey: PLMPLDIVJFPOKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.42
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  [4-(4-bromophenylethynyl)phenylethynyl]triisopropylsilane 在 正丁基锂 、 碘 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.17h， 以94%的产率得到2-[4-[2-(4-Iodophenyl)ethynyl]phenyl]ethynyl-tri(propan-2-yl)silane
  参考文献：
  名称：

  Electronic, Redox, and Photophysical Consequences of Metal-for-Carbon Substitution in Oligo-Phenylene-Ethynylenes

  摘要：

  The electronic structures, redox chemistry, and excited-state properties of tungsten-containing oligo-phenylene-ethynylenes (OPEs) of the form W[C(p-C6H4CC)(n-1)Ph](dppe)(2)Cl (n = 1-5; dppe =1,2-bis-(diphenylphosphino)ethane) are reported and compared with those of organic analogues in order to elucidate the effects of metal-for-carbon substitution on OPE bonding and electronic properties. Key similarities between the metallo- and organic OPEs that bear on materials-related functions include their nearly identical effective conjugation lengths, reduction potentials, and;14 orbital energies and delocalization. In addition to these conserved properties, the tungsten centers endow OPEs with reversible one-electron oxidation chemistry and long-lived emissive triplet excited states that are not accessible to organic OPEs. The electronic similarities and differences between metallo- and organic OPEs can be understood largely on the basis of pi/pi* orbital energy matching between tungsten and organic PE fragments and the introduction of an orthogonal mid-pi/pi*-gap d orbital in metallo-OPEs. These orbital energies can be tuned by varying the supporting ligands; this provides a means to rationally implement and control the emergent properties of metallo-OPE materials.

  DOI：

  10.1021/ja411354d
• 作为产物：
  描述：

  (4-溴苯基乙炔基)三甲基硅烷 在 bis-triphenylphosphine-palladium(II) chloride 、 四(三苯基膦)钯 sodium hydroxide 、 copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 26.0h， 生成 [4-(4-bromophenylethynyl)phenylethynyl]triisopropylsilane
  参考文献：
  名称：

  基于萘嵌苯染料的树突状多发色团的合成和表征，用于激发能的矢量传递。

  摘要：

  提出了基于刚性聚苯撑支架的树枝状多发色团的合成。不同的萘嵌苯生色团被并入树枝状聚合物的核心，分支和表面。以这种方式，获得了由三甲苯二酰亚胺核，坚硬的聚亚苯基支架和a单酰亚胺周边构成的两代树状二元体。此外，引入了第一种合成方法用于树突状三联体。该大分子的外球由萘单酰亚胺发色团形成，而per单酰亚胺基团位于树枝状支架中，并且r二酰亚胺发色团充当核心分子。该多色团在可见光谱的整个范围内吸收，并显示出分离良好的吸收包络线。

  DOI：

  10.1002/chem.200305359

文献信息

• Synthesis and Characterization of Dendritic Multichromophores Based on Rylene Dyes for Vectorial Transduction of Excitation Energy
  作者：Tanja Weil、Erik Reuther、Cornelia Beer、Klaus Müllen

  DOI：10.1002/chem.200305359

  日期：2004.3.19

  The synthesis of dendritic multichromophores based on a rigid polyphenylene scaffold is presented. Different rylene chromophores are incorporated into the core, the branches, and the surface of the dendrimer. In this way, two generations of dendritic dyads consisting of a terrylenediimide core, a stiff polyphenylene scaffold, and a perylenemonoimide periphery were obtained. Furthermore, the first synthetic

  提出了基于刚性聚苯撑支架的树枝状多发色团的合成。不同的萘嵌苯生色团被并入树枝状聚合物的核心，分支和表面。以这种方式，获得了由三甲苯二酰亚胺核，坚硬的聚亚苯基支架和a单酰亚胺周边构成的两代树状二元体。此外，引入了第一种合成方法用于树突状三联体。该大分子的外球由萘单酰亚胺发色团形成，而per单酰亚胺基团位于树枝状支架中，并且r二酰亚胺发色团充当核心分子。该多色团在可见光谱的整个范围内吸收，并显示出分离良好的吸收包络线。
• Electronic, Redox, and Photophysical Consequences of Metal-for-Carbon Substitution in Oligo-Phenylene-Ethynylenes
  作者：Daniel C. O’Hanlon、Brian W. Cohen、Davis B. Moravec、Richard F. Dallinger、Michael D. Hopkins

  DOI：10.1021/ja411354d

  日期：2014.2.26

  The electronic structures, redox chemistry, and excited-state properties of tungsten-containing oligo-phenylene-ethynylenes (OPEs) of the form W[C(p-C6H4CC)(n-1)Ph](dppe)(2)Cl (n = 1-5; dppe =1,2-bis-(diphenylphosphino)ethane) are reported and compared with those of organic analogues in order to elucidate the effects of metal-for-carbon substitution on OPE bonding and electronic properties. Key similarities between the metallo- and organic OPEs that bear on materials-related functions include their nearly identical effective conjugation lengths, reduction potentials, and;14 orbital energies and delocalization. In addition to these conserved properties, the tungsten centers endow OPEs with reversible one-electron oxidation chemistry and long-lived emissive triplet excited states that are not accessible to organic OPEs. The electronic similarities and differences between metallo- and organic OPEs can be understood largely on the basis of pi/pi* orbital energy matching between tungsten and organic PE fragments and the introduction of an orthogonal mid-pi/pi*-gap d orbital in metallo-OPEs. These orbital energies can be tuned by varying the supporting ligands; this provides a means to rationally implement and control the emergent properties of metallo-OPE materials.