5-bromo-2-((triisopropylsilyl)ethynyl)benzaldehyde | 1038395-11-7

• 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: 5-bromo-2-((triisopropylsilyl)ethynyl)benzaldehyde
• CAS: 1038395-11-7
• 化学式: C₁₈H₂₅BrOSi
• 分子量: 365.385
• InChiKey: HVJRACQMMUUWNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.83
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  5-bromo-2-((triisopropylsilyl)ethynyl)benzaldehyde 在 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.08h， 生成 methyl 2-((3-formyl-4-((triisopropylsilyl)ethynyl)phenyl)ethynyl)benzoate
  参考文献：
  名称：

  OPE/OPV H-mers: synthesis, electronic properties, and spectroscopic responses to binding with transition metal ions

  摘要：

  A new type of structurally defined H-shaped OPE/OPV co-oligomers (termed H-mers) functionalized with various donor and/or acceptor end groups was synthesized by iterative Sonogashira coupling and Horner-Wadsworth-Emmons (HWE) reactions. Electronic substitution effects on the H-mer backbone were investigated by UV-vis absorption and fluorescence spectroscopy. Some H-mers were found to show spectral responses upon binding to an acid (TFA) or transition metal ions, revealing the applicability of H-mers in the field of chromophore and fluorophore based chemosensors. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.012
• 作为产物：
  描述：

  (5-溴-2-碘苯基)甲醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 重铬酸吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 28.08h， 生成 5-bromo-2-((triisopropylsilyl)ethynyl)benzaldehyde
  参考文献：
  名称：

  OPE/OPV H-mers: synthesis, electronic properties, and spectroscopic responses to binding with transition metal ions

  摘要：

  A new type of structurally defined H-shaped OPE/OPV co-oligomers (termed H-mers) functionalized with various donor and/or acceptor end groups was synthesized by iterative Sonogashira coupling and Horner-Wadsworth-Emmons (HWE) reactions. Electronic substitution effects on the H-mer backbone were investigated by UV-vis absorption and fluorescence spectroscopy. Some H-mers were found to show spectral responses upon binding to an acid (TFA) or transition metal ions, revealing the applicability of H-mers in the field of chromophore and fluorophore based chemosensors. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.012

文献信息

• H-Shaped OPE/OPV Oligomers: A New Member of 2D-Conjugated Fluorophore Cores
  作者：Ningzhang Zhou、Li Wang、David W. Thompson、Yuming Zhao

  DOI：10.1021/ol8009623

  日期：2008.7.17

  A new class of two-dimensional (2D), pi-conjugated, skewed H-shaped co-oligomers of phenylene vinylene and phenylene ethynylene (11a-d, termed H-mers) were synthesized using Sonogashira coupling and Wittig-Horner reactions as the key steps. Electronic and spectroscopic properties of the H-mers were investigated by UV-vis absorption, fluorescence spectroscopic techniques, and ab initio calculations (HF/321G). Two amino-containing functional H-mers (11b and 11d) were found to exhibit appealing fluorescence sensitivity to selected Bronsted acids and transition-metal ions.