2-[4-[2-(4-乙炔基苯基)乙炔基]苯基]乙炔基-三甲基硅烷 | 189118-73-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[4-[2-(4-乙炔基苯基)乙炔基]苯基]乙炔基-三甲基硅烷
• 英文名称: ((4-((4-ethynylphenyl)ethynyl)phenyl)ethynyl)trimethylsilane
• 英文别名: 4-[p-(trimethylsilylethynyl)phenylethynyl]phenylacetylene；({4-[(4-Ethynylphenyl)ethynyl]phenyl}ethynyl)(trimethyl)silane；2-[4-[2-(4-ethynylphenyl)ethynyl]phenyl]ethynyl-trimethylsilane
• CAS: 189118-73-8
• 化学式: C₂₁H₁₈Si
• 分子量: 298.459
• InChiKey: MLISLPQCZANTDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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-[4-[2-(4-乙炔基苯基)乙炔基]苯基]乙炔基-三甲基硅烷 在 manganese(IV) oxide 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 一水合肼 、 二乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 17.0h， 生成 dimethyl 2-[[4-[(4-ethynylphenyl)ethynyl]phenyl]ethynyl]spiro[9H-fluorene-9,5'(4'aH)-pyrrolo[1,2-b]pyridazine]-6',7'-dicarboxylate
  参考文献：
  名称：

  二氢吲哚并嗪的光致变色。第XV部分：带有共轭亚芳基乙炔撑三脚架连接系统的二氢吲哚嗪光开关的合成和光物理性质

  摘要：

  摘要使用几种Sonogashira偶联反应合成了带有共轭亚芳基乙炔基三脚架连接系统的不同光致变色二氢吲哚并二酮（DHI）。通过化学和光化学途径合成了在芴部分的2-位掺入不同炔键部分的螺环丙烯前体。研究了在芴（A区）和哒嗪（C区）部分取代的DHI衍生物的多址光致变色特性。还通过应用不同的钯介导的Sonogashira偶联反应来优化DHI的形成。用多色光照射光致变色DHI会导致有色甜菜碱经历热1,5-电环化。热力学1，使用多通道FT-UV-Vis分光光度计研究了5电环化。通过将取代从未取代的取代为二甲基取代的哒嗪，可以观察到对甜菜碱的1,5-电环化过程动力学行为的显着影响。光降解实验以及漂白和褪色循环表明所研究的甜菜具有很高的光稳定性。三脚架接头共轭物甜菜碱的这些特性将有助于这些材料的应用。光降解实验以及漂白和褪色循环表明所研究的甜菜具有很高的光稳定性。三脚架接头共轭物甜菜碱的这些特性将有助于

  DOI：

  10.1007/s00706-010-0267-7
• 作为产物：
  描述：

  4-三甲基硅乙炔基苯甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 二异丙胺 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 2-[4-[2-(4-乙炔基苯基)乙炔基]苯基]乙炔基-三甲基硅烷
  参考文献：
  名称：

  Synthesis and Characterization of Redox-Active Mononuclear Fe(κ²-dppe)(η⁵-C₅Me₅)-Terminated π-Conjugated Wires

  摘要：

  Several new redox-active Fe(kappa(2)-dppe)(eta(5)-C5Me5) arylacetylide complexes featuring pendant ethynyl (Fe(kappa(2)-dppe)(eta(5)-C5Me5)-[{C equivalent to C(1,4-C6H4)}(n)C equivalent to CH] (1b-d; n = 1-3), Fe(kappa(2)-dppe)(eta(5)-C5Me5)[C equivalent to C(1,3-C6H4)C equivalent to CH] (2)) or ethenyl (Fe(kappa(2)-dppe)(eta(5)-C5Me5)[CE equivalent to C(1,4-C6H4)CH equivalent to CH2] (3)) groups have been synthesized and characterized under their Fe(II) and Fe(III) states. In contrast to the known ethynyl Fe(III) complex [Fe(kappa(2)-dppe)(eta(5)-C5Me5)(C7 equivalent to CH)][PF6] (1a[PF6]), most of the new Fe(III) derivatives turned out to be kinetically stable in solution. A consistent picture of the electronic structure of the latter complexes in both redox states emerged from experimental data and DFT calculations. This study revealed that beyond the first 1,4-phenylene ring, modification or extension of the carbon-rich linker using (4-phenylene)ethynylene spacers will have only a minor influence on their electronic properties in their ground state, while still maintaining some (weak) electronic interaction along the carbon-rich backbone.

  DOI：

  10.1021/om400515g

文献信息

• Synthesis of conjugated 2,7-bis(trimethylsilylethynyl)-(phenylethynyl)nfluoren-9-one and 9-(p-methoxyphenyl)-9-methyl derivatives: optical properties
  作者：J. Gonzalo Rodríguez、J. Luis Tejedor、Teresa La Parra、Cristina Díaz

  DOI：10.1016/j.tet.2006.01.058

  日期：2006.4

  fluorene have been synthesized and their fluorescence properties analyzed. The synthesis of conjugated 2,7-bis(trimethylsilylethynyl)-(phenylethynyl)nfluoren-9-one (or the 9-(p-methoxyphenyl)-9-methyl) structures was carried out by the heterocoupling reaction between the 2,7-di(halo)fluoren-9-one (or 2,7-dibromo-9-(p-methoxyphenyl)-9-methylfluorene) and p-trimethylsilylethynyl(phenylethynyl)n (n=1,2), catalyzed

  已经合成了2，7-取代的9-芴酮和9，9-二取代的芴，并分析了它们的荧光性质。通过2,7之间的杂偶联反应进行共轭2,7-双（三甲基甲硅烷基乙炔基）-（苯基乙炔基）n芴-9-（或9-（对甲氧基苯基）-9-甲基）结构的合成-二（卤）芴-9-一（或2,7-二溴-9-（对甲氧基苯基）-9-甲基芴）和对-三甲基甲硅烷基乙炔基（苯基乙炔基）n（n = 1,2），由二氯催化双（三苯基膦）钯和碘化亚铜体系，呈发散性合成。
• Photochromism of dihydroindolizines. Part 12: synthesis and photochromism of novel π-conjugated rigid dihydroindolizines as potential molecular electronic devices
  作者：Saleh Abdel-Mgeed Ahmed

  DOI：10.1016/j.tet.2008.12.047

  日期：2009.2

  Novel carbon-rich photochromic dihydroindolizine DHI derivatives and new spirocyclopropenes have been synthesized. Three alternative synthetic pathways for the synthesis of DHI 10 have been established. Different Sonogashira-mediated coupling reactions have been applied to optimize the reaction conditions and to obtain the best yields. Palladium-mediated Sonogashira coupling of DHIs with 4-(thioacetyl)iodobenzene

  已经合成了新型的富碳光致变色二氢吲哚嗪DHI衍生物和新的螺环丙烯。已经建立了用于合成DHI 10的三种替代合成途径。已经应用了不同的Sonogashira介导的偶联反应，以优化反应条件并获得最佳收率。钯介导的DHI与4-（硫代乙酰基）碘苯13和碘苯17的Sonogashira偶联产生偶联产物，在分子电子学中具有潜在的应用。光致变色DHI 10a – f，12a – f，14a – f，16a –的辐照f和18a – f用多色光导致甜菜碱9a – f，13a – f，15a – f，17a – f和19a – f。有色甜菜碱形式 在室温下浓度为1×10 -5 mol / L的CH 2 Cl 2溶液中是显而易见的，因为它们的1,5-电环化较慢。发现有色甜菜碱的所有吸收最大值都在可见光区域，位于524（甜菜碱9a）和639 nm（甜菜碱15f）之间。）。使用多通道紫外可见分光光度法研究了热1，5
• Photochromism of tetrahydroindolizines. Part XIV: synthesis of cis-fixed conjugated photochromic pyridazinopyrrolo[1,2-b]isoquinolines incorporating carbon-rich linkers
  作者：Saleh A. Ahmed、Khalid S. Khairou、Basim H. Asghar、Hussni A. Muathen、Nariman M.A. Nahas、Hossa F. Alshareef

  DOI：10.1016/j.tetlet.2014.02.078

  日期：2014.4

  New carbon-rich photochromic tetrahydroindolizines (THIs) bearing dihydroisoquinoline derivatives as heterocyclic bases (region B) have been synthesized via different chemical and photochemical pathways. Three alternative pathways for the synthesis of the target photochromic THI-based pyridazinopyrrolo-[1,2-b]isoquinolines via in situ trapping with hydrazine hydrate have been established. In order to obtain high product yields, different Sonogashira-mediated coupling reactions have been optimized. Low temperature multichannel UV-vis and flash photolysis techniques were used to detect the photochromic and kinetic properties of the synthesized system. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis and Characterization of Redox-Active Mononuclear Fe(κ²-dppe)(η⁵-C₅Me₅)-Terminated π-Conjugated Wires
  作者：Katy Green、Nicolas Gauthier、Hiba Sahnoune、Gilles Argouarch、Loic Toupet、Karine Costuas、Arnaud Bondon、Bruno Fabre、Jean-François Halet、Frédéric Paul

  DOI：10.1021/om400515g

  日期：2013.8.12

  Several new redox-active Fe(kappa(2)-dppe)(eta(5)-C5Me5) arylacetylide complexes featuring pendant ethynyl (Fe(kappa(2)-dppe)(eta(5)-C5Me5)-[C equivalent to C(1,4-C6H4)}(n)C equivalent to CH] (1b-d; n = 1-3), Fe(kappa(2)-dppe)(eta(5)-C5Me5)[C equivalent to C(1,3-C6H4)C equivalent to CH] (2)) or ethenyl (Fe(kappa(2)-dppe)(eta(5)-C5Me5)[CE equivalent to C(1,4-C6H4)CH equivalent to CH2] (3)) groups have been synthesized and characterized under their Fe(II) and Fe(III) states. In contrast to the known ethynyl Fe(III) complex [Fe(kappa(2)-dppe)(eta(5)-C5Me5)(C7 equivalent to CH)][PF6] (1a[PF6]), most of the new Fe(III) derivatives turned out to be kinetically stable in solution. A consistent picture of the electronic structure of the latter complexes in both redox states emerged from experimental data and DFT calculations. This study revealed that beyond the first 1,4-phenylene ring, modification or extension of the carbon-rich linker using (4-phenylene)ethynylene spacers will have only a minor influence on their electronic properties in their ground state, while still maintaining some (weak) electronic interaction along the carbon-rich backbone.
• Photochromism of dihydroindolizines. Part XV: Synthesis and photophysical properties of dihydroindolizine photoswitches bearing a conjugated aryleneethynylene tripodal linker system
  作者：Saleh A. Ahmed、Shaya Y. Al-Raqa

  DOI：10.1007/s00706-010-0267-7

  日期：2010.3

  reactions. Irradiation of the photochromic DHIs with polychromatic light led to colored betaines which undergo thermal 1,5-electrocyclization. The kinetics of the thermal 1,5-electrocyclization were studied by using a multichannel FT–UV–Vis spectrophotometer. A pronounced effect on the kinetic behavior of the 1,5-electrocyclization process of the betaines was observed by changing substitution from non-substituted

  摘要使用几种Sonogashira偶联反应合成了带有共轭亚芳基乙炔基三脚架连接系统的不同光致变色二氢吲哚并二酮（DHI）。通过化学和光化学途径合成了在芴部分的2-位掺入不同炔键部分的螺环丙烯前体。研究了在芴（A区）和哒嗪（C区）部分取代的DHI衍生物的多址光致变色特性。还通过应用不同的钯介导的Sonogashira偶联反应来优化DHI的形成。用多色光照射光致变色DHI会导致有色甜菜碱经历热1,5-电环化。热力学1，使用多通道FT-UV-Vis分光光度计研究了5电环化。通过将取代从未取代的取代为二甲基取代的哒嗪，可以观察到对甜菜碱的1,5-电环化过程动力学行为的显着影响。光降解实验以及漂白和褪色循环表明所研究的甜菜具有很高的光稳定性。三脚架接头共轭物甜菜碱的这些特性将有助于这些材料的应用。光降解实验以及漂白和褪色循环表明所研究的甜菜具有很高的光稳定性。三脚架接头共轭物甜菜碱的这些特性将有助于