1,4-bis[3-({4-[(triisopropylsilyl)ethynyl]pyridin-3-yl}ethynyl)pyridin-4-yl]buta-1,3-diyne | 860021-97-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1,4-bis[3-({4-[(triisopropylsilyl)ethynyl]pyridin-3-yl}ethynyl)pyridin-4-yl]buta-1,3-diyne
• 英文别名: Tri(propan-2-yl)-[2-[3-[2-[4-[4-[3-[2-[4-[2-tri(propan-2-yl)silylethynyl]pyridin-3-yl]ethynyl]pyridin-4-yl]buta-1,3-diynyl]pyridin-3-yl]ethynyl]pyridin-4-yl]ethynyl]silane
• CAS: 860021-97-2
• 化学式: C₅₀H₅₄N₄Si₂
• 分子量: 767.177
• InChiKey: RSLMRYILHVJHLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.61
• 重原子数：
  56
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-bis[3-({4-[(triisopropylsilyl)ethynyl]pyridin-3-yl}ethynyl)pyridin-4-yl]buta-1,3-diyne 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 20.0h， 以99%的产率得到1,4-bis{3-[(4-ethynylpyridin-3-yl)ethynyl]pyridin-4-yl}buta-1,3-diyne
  参考文献：
  名称：

  Nitrogen Heterocyclic Carbon-Rich Materials:  Synthesis and Spectroscopic Properties of Dehydropyridoannulene Macrocycles

  摘要：

  A new series of nitrogen heterocyclic dehydroannulenes 1-3 have been synthesized and their macrocyclic structures assigned using spectroscopic methods. The chiral and planar ground state conformations of 1 and 3, respectively, were determined by semiempirical theoretical calculations. All dehydropyridoannulenes and precursors possessing four aromatic rings functioned as fluorescent chromophores. A detailed spectroscopic investigation into the cation-binding properties of 3 in dilute solution revealed a particularly selective photoluminescence quenching sensory response for Pd-II ions. Cycle 3, as well as 1 and 2, also exhibited reversible proton-triggered luminescence quenching behavior. At higher concentrations, 3 afforded a coordination polymer precipitate with Ag-I ions. Cycles I and 2 and precursors 15, 23, and 29 also undergo thermochemical reactions that may potentially lead to carbon-rich polymers. The physicochemical properties of 1-3 suggest that dehydropyridoarmulenes may serve as a particularly versatile new class of ligands for the creation of novel heteroatom-containing carbon-rich materials with many potential applications in supramolecular materials science and nanotechnology.

  DOI：

  10.1021/jo040276f
• 作为产物：
  描述：

  3-溴-4-碘吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 copper(l) iodide 、 正丁基锂 、 三乙胺 作用下， 以 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 194.5h， 生成 1,4-bis[3-({4-[(triisopropylsilyl)ethynyl]pyridin-3-yl}ethynyl)pyridin-4-yl]buta-1,3-diyne
  参考文献：
  名称：

  Nitrogen Heterocyclic Carbon-Rich Materials:  Synthesis and Spectroscopic Properties of Dehydropyridoannulene Macrocycles

  摘要：

  A new series of nitrogen heterocyclic dehydroannulenes 1-3 have been synthesized and their macrocyclic structures assigned using spectroscopic methods. The chiral and planar ground state conformations of 1 and 3, respectively, were determined by semiempirical theoretical calculations. All dehydropyridoannulenes and precursors possessing four aromatic rings functioned as fluorescent chromophores. A detailed spectroscopic investigation into the cation-binding properties of 3 in dilute solution revealed a particularly selective photoluminescence quenching sensory response for Pd-II ions. Cycle 3, as well as 1 and 2, also exhibited reversible proton-triggered luminescence quenching behavior. At higher concentrations, 3 afforded a coordination polymer precipitate with Ag-I ions. Cycles I and 2 and precursors 15, 23, and 29 also undergo thermochemical reactions that may potentially lead to carbon-rich polymers. The physicochemical properties of 1-3 suggest that dehydropyridoarmulenes may serve as a particularly versatile new class of ligands for the creation of novel heteroatom-containing carbon-rich materials with many potential applications in supramolecular materials science and nanotechnology.

  DOI：

  10.1021/jo040276f

文献信息

• Nitrogen Heterocyclic Carbon-Rich Materials:  Synthesis and Spectroscopic Properties of Dehydropyridoannulene Macrocycles
  作者：Paul N. W. Baxter、Riad Dali-Youcef

  DOI：10.1021/jo040276f

  日期：2005.6.1

  A new series of nitrogen heterocyclic dehydroannulenes 1-3 have been synthesized and their macrocyclic structures assigned using spectroscopic methods. The chiral and planar ground state conformations of 1 and 3, respectively, were determined by semiempirical theoretical calculations. All dehydropyridoannulenes and precursors possessing four aromatic rings functioned as fluorescent chromophores. A detailed spectroscopic investigation into the cation-binding properties of 3 in dilute solution revealed a particularly selective photoluminescence quenching sensory response for Pd-II ions. Cycle 3, as well as 1 and 2, also exhibited reversible proton-triggered luminescence quenching behavior. At higher concentrations, 3 afforded a coordination polymer precipitate with Ag-I ions. Cycles I and 2 and precursors 15, 23, and 29 also undergo thermochemical reactions that may potentially lead to carbon-rich polymers. The physicochemical properties of 1-3 suggest that dehydropyridoarmulenes may serve as a particularly versatile new class of ligands for the creation of novel heteroatom-containing carbon-rich materials with many potential applications in supramolecular materials science and nanotechnology.