1,4-bis[2-((4-ethynylpyridin-3-yl)ethynyl)phenyl]buta-1,3-diyne | 860022-02-2

• 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[2-((4-ethynylpyridin-3-yl)ethynyl)phenyl]buta-1,3-diyne
• 英文别名: 4-Ethynyl-3-[2-[2-[4-[2-[2-(4-ethynylpyridin-3-yl)ethynyl]phenyl]buta-1,3-diynyl]phenyl]ethynyl]pyridine
• CAS: 860022-02-2
• 化学式: C₃₄H₁₆N₂
• 分子量: 452.514
• InChiKey: BNIBHSCIMAIUDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-bis[2-((4-ethynylpyridin-3-yl)ethynyl)phenyl]buta-1,3-diyne 在 吡啶 、 [Cu2(OAc)4(H2O)2] 作用下， 以 甲苯 为溶剂， 反应 600.0h， 以79%的产率得到6,17-Diazapentacyclo[30.4.0.04,9.014,19.022,27]hexatriaconta-1(36),4(9),5,7,14(19),15,17,22,24,26,32,34-dodecaen-2,10,12,20,28,30-hexayne
  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-ethynyl-4-triisopropylsilylethynylpyridine 在 bis-triphenylphosphine-palladium(II) chloride 吡啶 、 copper(l) iodide 、 四丁基氟化铵 、 氧气 、 potassium carbonate 、 三乙胺 、 copper(l) chloride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 217.5h， 生成 1,4-bis[2-((4-ethynylpyridin-3-yl)ethynyl)phenyl]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