4,4'-dibromo-2,2'-bis[(trimethylsilyl)ethynyl]-1,1'-biphenyl

• 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'-dibromo-2,2'-bis[(trimethylsilyl)ethynyl]-1,1'-biphenyl
• 英文别名: 2-[5-Bromo-2-[4-bromo-2-(2-trimethylsilylethynyl)phenyl]phenyl]ethynyl-trimethylsilane；2-[5-bromo-2-[4-bromo-2-(2-trimethylsilylethynyl)phenyl]phenyl]ethynyl-trimethylsilane
• 化学式: C₂₂H₂₄Br₂Si₂
• 分子量: 504.412
• InChiKey: LMJLVEHXOZLXKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.34
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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'-dibromo-2,2'-bis[(trimethylsilyl)ethynyl]-1,1'-biphenyl 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 以75%的产率得到4,4'-dibromo-2,2'-diethynyl-1,1'-biphenyl
  参考文献：
  名称：

  Bottom-Up Synthesis of Necklace-Like Graphene Nanoribbons

  摘要：

  AbstractGraphene nanoribbons (GNRs) with an unprecedented “necklace‐like” structure were synthesized through a bottom‐up chemical approach, based on the oxidative cyclodehydrogenation of tailor‐made polyphenylene precursors. A polycyclic aromatic hydrocarbon consisting of 84 sp2 carbons (C84) was also synthesized and characterized as a model compound. Characterizations by a combination of MALDI‐TOF MS and FTIR, Raman, and UV/Vis absorption spectroscopy validated the formation of the necklace‐like GNRs. The absorption spectrum and DFT calculations revealed a bandgap of approximately 1.4 eV for this novel GNR system, which has not been attained with other GNR structures, enabling further fine‐tuning of GNR bandgaps by structural modulation.

  DOI：

  10.1002/asia.201500450
• 作为产物：
  描述：

  2,5-二溴硝基苯 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 tin 、 铜 、 copper(II) iodide 、 sodium nitrite 作用下， 以 乙醇 、 水 、 三乙胺 为溶剂， 反应 27.0h， 生成 4,4'-dibromo-2,2'-bis[(trimethylsilyl)ethynyl]-1,1'-biphenyl
  参考文献：
  名称：

  Bottom-Up Synthesis of Necklace-Like Graphene Nanoribbons

  摘要：

  AbstractGraphene nanoribbons (GNRs) with an unprecedented “necklace‐like” structure were synthesized through a bottom‐up chemical approach, based on the oxidative cyclodehydrogenation of tailor‐made polyphenylene precursors. A polycyclic aromatic hydrocarbon consisting of 84 sp2 carbons (C84) was also synthesized and characterized as a model compound. Characterizations by a combination of MALDI‐TOF MS and FTIR, Raman, and UV/Vis absorption spectroscopy validated the formation of the necklace‐like GNRs. The absorption spectrum and DFT calculations revealed a bandgap of approximately 1.4 eV for this novel GNR system, which has not been attained with other GNR structures, enabling further fine‐tuning of GNR bandgaps by structural modulation.

  DOI：

  10.1002/asia.201500450