5,5′-di(1-butyl-1,2,3-triazol-4-yl)-2,2′-bipyridine | 1413941-50-0

• 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: 5,5′-di(1-butyl-1,2,3-triazol-4-yl)-2,2′-bipyridine
• 英文别名: 5-(1-Butyltriazol-4-yl)-2-[5-(1-butyltriazol-4-yl)pyridin-2-yl]pyridine
• CAS: 1413941-50-0
• 化学式: C₂₂H₂₆N₈
• 分子量: 402.502
• InChiKey: QWWODEQWUDQKDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  87.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  六氟磷酸钾 、 顺-双(2,2-二吡啶)二氯化钌(II) 水合物 、 5,5′-di(1-butyl-1,2,3-triazol-4-yl)-2,2′-bipyridine 以 乙二醇 、 水 为溶剂， 反应 0.5h， 以76%的产率得到[Ru(bpy)₂(Bu-dtabpyH)](PF6)₂
  参考文献：
  名称：

  Redox-Asymmetric Bisruthenium Complex Bridged by a Pyridin-4-yl Moiety: Synthesis, Characterization, and Electronic Coupling Studies

  摘要：

  A polyazine ligand, 5,5'-di(1-butyl-1,2,3-triazol-4-yl)-2,2'-bipyridine (Bu-dtabpyH), has been prepared by a "click" reaction. The treatment of Bu-dtabpyH with [Ru(bpy)(2)Cl-2] affords complex [Ru(bpy)(2)(Bu-dtabpyH)](2+) (bpy = 2,2'-bipyridine), which has been characterized by single-crystal X-ray analysis. The reaction of [Ru(bpy)(2)(Bu-dtabpyH)](2+) with another equivalent of [Ru(bpy)(2)Cl-2] in the presence of AgOTf gives a redox-asymmetric bisruthenium complex, [Ru(bpy)(2)(Bu-dtabpy)Ru(bpy)(2)](3+) (Bu-dtabpy is the 4-deprotonated form of Bu-dtabpyH), with one ruthenium atom binding to the pyridin-4-yl bridge with a Ru-N bond and the other with a Ru-C bond. This complex displays two Ru(II/III) redox couples at +0.79 and +1.28 V vs Ag/AgCl. After being transformed into a mixed-valence species, [Ru(bpy)(2)(Bu-dtabpy)Ru(bpy)(2)](4+), by one-electron oxidation, it exhibits a moderate metal-to-metal charge-transfer band around 1300 nm. Density functional theory and time-dependent density functional theory calculations have been carried out for the model complex [Ru(bpy)(2)(Me-dtabpy)Ru(bpy)(2)](3+) and the mixed-valence state [Ru(bpy)(2)(Me-dtabpy)Ru(bpy)(2)](4+) to complement these experimental results, where Me-dtabpy is the 4-deprotonated form of 5,5'-di(1-methyl-1,2,3-triazol-4-yl)-2,2'-bipyridine.

  DOI：

  10.1021/om3009662
• 作为产物：
  描述：

  5,5'-二溴-2,2'-联吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 ammonium hydroxide 、 copper(l) iodide 、 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 sodium ascorbate 、 二异丙胺 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 44.0h， 生成 5,5′-di(1-butyl-1,2,3-triazol-4-yl)-2,2′-bipyridine
  参考文献：
  名称：

  Redox-Asymmetric Bisruthenium Complex Bridged by a Pyridin-4-yl Moiety: Synthesis, Characterization, and Electronic Coupling Studies

  摘要：

  A polyazine ligand, 5,5'-di(1-butyl-1,2,3-triazol-4-yl)-2,2'-bipyridine (Bu-dtabpyH), has been prepared by a "click" reaction. The treatment of Bu-dtabpyH with [Ru(bpy)(2)Cl-2] affords complex [Ru(bpy)(2)(Bu-dtabpyH)](2+) (bpy = 2,2'-bipyridine), which has been characterized by single-crystal X-ray analysis. The reaction of [Ru(bpy)(2)(Bu-dtabpyH)](2+) with another equivalent of [Ru(bpy)(2)Cl-2] in the presence of AgOTf gives a redox-asymmetric bisruthenium complex, [Ru(bpy)(2)(Bu-dtabpy)Ru(bpy)(2)](3+) (Bu-dtabpy is the 4-deprotonated form of Bu-dtabpyH), with one ruthenium atom binding to the pyridin-4-yl bridge with a Ru-N bond and the other with a Ru-C bond. This complex displays two Ru(II/III) redox couples at +0.79 and +1.28 V vs Ag/AgCl. After being transformed into a mixed-valence species, [Ru(bpy)(2)(Bu-dtabpy)Ru(bpy)(2)](4+), by one-electron oxidation, it exhibits a moderate metal-to-metal charge-transfer band around 1300 nm. Density functional theory and time-dependent density functional theory calculations have been carried out for the model complex [Ru(bpy)(2)(Me-dtabpy)Ru(bpy)(2)](3+) and the mixed-valence state [Ru(bpy)(2)(Me-dtabpy)Ru(bpy)(2)](4+) to complement these experimental results, where Me-dtabpy is the 4-deprotonated form of 5,5'-di(1-methyl-1,2,3-triazol-4-yl)-2,2'-bipyridine.

  DOI：

  10.1021/om3009662