1,4-bis[4-trimethylsilyl-2-(trimethylsilylethynyl)but-1-en-3-ynyl]benzene | 360549-86-6

• 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: 1,4-bis[4-trimethylsilyl-2-(trimethylsilylethynyl)but-1-en-3-ynyl]benzene
• 英文别名: Trimethyl-[5-trimethylsilyl-3-[[4-[4-trimethylsilyl-2-(2-trimethylsilylethynyl)but-1-en-3-ynyl]phenyl]methylidene]penta-1,4-diynyl]silane
• CAS: 360549-86-6
• 化学式: C₃₀H₄₂Si₄
• 分子量: 515.005
• InChiKey: DMFNINMFMRHECJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.98
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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-溴吡啶 、 1,4-bis[4-trimethylsilyl-2-(trimethylsilylethynyl)but-1-en-3-ynyl]benzene 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium fluoride 、 copper(l) iodide 作用下， 以 甲醇 、 三乙胺 为溶剂， 反应 4.0h， 以56%的产率得到1,4-bis[4-(4-pyridyl)-2-(4-pyridylethynyl)but-1-en-3-ynyl]benzene
  参考文献：
  名称：

  Synthesis and Photophysical Studies of Bis-enediynes as Tunable Fluorophores

  摘要：

  We have synthesized a family of bis-enediynes by two complementary Pd/Cu-catalyzed Sonogashira cross-coupling methods. One is a modified Sonogashira reaction between the TMS-protected tetraalkyne 20 (or 21) and various aromatic bromides to afford bis-enediynes 22a-d and 23a-d bearing different peripheral aryl units. The other, the reaction of bifunctional 1,1-dibromo-1-alkenes with phenylacetylene, afforded a series of bis-enediynes 24-32 bearing various core aryl groups. These chemical modifications to the core and periphery of bis-enediynes induce dramatic changes in absorption and emission spectra. Bis-enediynes 22 and 23 show a large Stokes shift of about 50-110 nm when compared to the less-conjugated bis-enediynes 20 and 21. Absorptions and emissions of bis-enediynes 25, 27-29, and 31 were red-shifted relative to those of enediyne 35. Substantial increases in fluorescence quantum yields are observed as a result of extending the T-conjugation. The emission wavelength of bis-enediynes was tailored from indigo blue to reddish-orange, suggesting that the color of emission can be tunable by modification of the core and/or peripheral units.

  DOI：

  10.1021/ja0349148
• 作为产物：
  描述：

  1,4-双(2,2-二溴乙烯基)苯 、 三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 作用下， 以 三乙胺 为溶剂， 反应 2.0h， 以91%的产率得到1,4-bis[4-trimethylsilyl-2-(trimethylsilylethynyl)but-1-en-3-ynyl]benzene
  参考文献：
  名称：

  Novel Fluorophores:  Efficient Synthesis and Photophysical Study

  摘要：

  [GRAPHICS]We have synthesized novel fluorophores by using Sonogashira reactions of 1,4-bis(dibromovinyl)benzene and 2,5-bis(dibromovinyl)thiophene with various aromatic bromides. The emission maxima of these fluorophores vary from the indigo blue to the reddish-orange region, depending on the structures of aromatic nuclei and peripheral moieties.

  DOI：

  10.1021/ol0162264

文献信息

• Novel Fluorophores:  Efficient Synthesis and Photophysical Study
  作者：Gil Tae Hwang、Hyung Su Son、Ja Kang Ku、Byeang Hyean Kim

  DOI：10.1021/ol0162264

  日期：2001.8.9

  [GRAPHICS]We have synthesized novel fluorophores by using Sonogashira reactions of 1,4-bis(dibromovinyl)benzene and 2,5-bis(dibromovinyl)thiophene with various aromatic bromides. The emission maxima of these fluorophores vary from the indigo blue to the reddish-orange region, depending on the structures of aromatic nuclei and peripheral moieties.
• Synthesis and Photophysical Studies of Bis-enediynes as Tunable Fluorophores
  作者：Gil Tae Hwang、Hyung Su Son、Ja Kang Ku、Byeang Hyean Kim

  DOI：10.1021/ja0349148

  日期：2003.9.1

  We have synthesized a family of bis-enediynes by two complementary Pd/Cu-catalyzed Sonogashira cross-coupling methods. One is a modified Sonogashira reaction between the TMS-protected tetraalkyne 20 (or 21) and various aromatic bromides to afford bis-enediynes 22a-d and 23a-d bearing different peripheral aryl units. The other, the reaction of bifunctional 1,1-dibromo-1-alkenes with phenylacetylene, afforded a series of bis-enediynes 24-32 bearing various core aryl groups. These chemical modifications to the core and periphery of bis-enediynes induce dramatic changes in absorption and emission spectra. Bis-enediynes 22 and 23 show a large Stokes shift of about 50-110 nm when compared to the less-conjugated bis-enediynes 20 and 21. Absorptions and emissions of bis-enediynes 25, 27-29, and 31 were red-shifted relative to those of enediyne 35. Substantial increases in fluorescence quantum yields are observed as a result of extending the T-conjugation. The emission wavelength of bis-enediynes was tailored from indigo blue to reddish-orange, suggesting that the color of emission can be tunable by modification of the core and/or peripheral units.