4,4'-azobis(2,2'-bipyridine) | 1144521-82-3

• 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: 4,4'-azobis(2,2'-bipyridine)
• 英文别名: azobpy；6,6''-azobis(2,2'-bipyridine)；Bis(6-pyridin-2-ylpyridin-2-yl)diazene
• CAS: 1144521-82-3
• 化学式: C₂₀H₁₄N₆
• 分子量: 338.371
• InChiKey: OXRPJAZNFFKTQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  顺-双(2,2'-二吡啶基)二氯化钌(II)二水合物 、 4,4'-azobis(2,2'-bipyridine) 以 乙醇 、 水 为溶剂， 反应 8.0h， 以60%的产率得到[Ru(bpy)2(azobpy)Ru(bpy)2]Cl4
  参考文献：
  名称：

  Colorimetric and luminescent dual-signaling responsive probing of thiols by a ruthenium(II)-azo complex

  摘要：

  A dinuclear ruthenium(II) complex linked via a reducible azo group [Ru(bpy)(2)(azobpy)Ru(bpy)(2)]Cl-4 (Ru(2)azo, bpy=2,2'-bipyridine, azobpy=4,4 ''-azobis (2,2'-bipyridine)) was adopted as a probe for thiols. Results showed that Ru(2)azo could selectively and effectively react with biological thiols (such as cysteine, homocysteine and glutathione) with a 10(-7) M detection limit. After it reacted with thiols, the original gray color of Ru(2)azo solution immediately turned yellow and the luminescence significantly enhanced, showing "naked-eye" colorimetric and "off-on" luminescent dual-signaling response for thiols. Mechanism studies demonstrated that Ru(2)azo reacted with thiols undergoing a two-electron transfer process, forming the azo(2-) anion product. (c) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2012.12.019

文献信息

• 6,6″-Azobis(2,2′-bipyridine) and Its Dinuclear Ruthenium Complex: A Comparative Study with Positional Isomers
  作者：Joe Otsuki、Izumi Kurihara、Arata Imai、Yuki Hamada、Nobuyuki Omokawa

  DOI：10.1246/bcsj.80.902

  日期：2007.5.15

  signals in the part of the 6-azobpy ligand. The analysis of 1 H NMR spectra clearly identified the structure of the complex, in which the Ru 2+ ions are chelated by the bpy parts of the bridging 6-azobpy ligand. Electronic absorption and electrochemical properties are characterized by the presence of a low-lying π*level of the bridging ligand, manifested by a metal-to-ligand charge-transfer band extending

  表现为金属到配体的电荷转移带延伸至 800 nm，以及循环伏安法中负电位相对较低的两个连续单电子还原波。借助密度泛函理论 (DFT)、瞬态 DFT 和 ZINDO 计算，将这些特性与先前报道的位置异构体的特性进行了比较。Ru 3+/2+ 氧化还原对的分析表明，非对映异构体之间的氧化还原电位略有不同，并且存在金属间电子相互作用。