1,2-di(2,2'-bipyridin-5-yl)ethane

• 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: 1,2-di(2,2'-bipyridin-5-yl)ethane
• 英文别名: 1,2-bis(bipyridine-6'-yl)ethane；6,6'-(ethan-1,2-diyl)bis-2,2'-bipyridine；O-bpy；2-Pyridin-2-yl-5-[2-(6-pyridin-2-ylpyridin-3-yl)ethyl]pyridine；2-pyridin-2-yl-5-[2-(6-pyridin-2-ylpyridin-3-yl)ethyl]pyridine
• 化学式: C₂₂H₁₈N₄
• 分子量: 338.412
• InChiKey: KMZSQWKJFGMAQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  1,2-di(2,2'-bipyridin-5-yl)ethane 、 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以68 mg的产率得到
  参考文献：
  名称：

  Electrochemiluminescent dinuclear Ru(II) complexes assembled with 1,1′-(1,2-ethynediyl)- or dimethlyene-bridged bis(bipyridine) ligands: Synthesis and photophysical and electrochemical properties

  摘要：

  1,2-Di(2,2'-bipyridin-5-yl) ethane (BL1) and 1,2-di(2,2'-bipyridin-5-yl)ethyne (BL2) were synthesized as new bridging ligands and coordinated to (RuL2(acetone)(2))(PF6)(2) for the preparation of various [Ru(L)(2) (BL) Ru(L)(2)](PF6)(4)-type dinuclear ruthenium complexes (where BL = BL1, BL2 and L = bpy, o-phen, DTDP). The electrochemical redox potentials, spectroscopic properties, and relative electrochemiluminescence intensity of BL1 and BL2 were characterized and compared to those of well-known tris(1,10-phenanthroline) rutheniun(II) [Ru(o-phen)(3)](PF6)(2)] complex as a reference. Dinuclear Ru(II) complexes containing the conjugated bridging ligand (BL2) showed much more intense electrochemiluminescent responses than dinuclear Ru(II) complexes with the non-conjugated bridging ligand (BL1). Among the complexes with conjugated bridging ligands, [(DTDP)(2)Ru(bpy-CC-bpy)Ru(DTDP)(2)](PF6)(4) exhibited enhanced ECL intensities as high as 3.6 times greater than that of the reference, [Ru(o-phen)(3)](PF6)(2). (C)2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.10.028
• 作为产物：
  描述：

  2-(三甲基甲锡烷基)吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium tetrahydroborate 、 硫酸 、 氢溴酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 间二甲苯 为溶剂， 反应 46.0h， 生成 1,2-di(2,2'-bipyridin-5-yl)ethane
  参考文献：
  名称：

  Electrochemiluminescent dinuclear Ru(II) complexes assembled with 1,1′-(1,2-ethynediyl)- or dimethlyene-bridged bis(bipyridine) ligands: Synthesis and photophysical and electrochemical properties

  摘要：

  1,2-Di(2,2'-bipyridin-5-yl) ethane (BL1) and 1,2-di(2,2'-bipyridin-5-yl)ethyne (BL2) were synthesized as new bridging ligands and coordinated to (RuL2(acetone)(2))(PF6)(2) for the preparation of various [Ru(L)(2) (BL) Ru(L)(2)](PF6)(4)-type dinuclear ruthenium complexes (where BL = BL1, BL2 and L = bpy, o-phen, DTDP). The electrochemical redox potentials, spectroscopic properties, and relative electrochemiluminescence intensity of BL1 and BL2 were characterized and compared to those of well-known tris(1,10-phenanthroline) rutheniun(II) [Ru(o-phen)(3)](PF6)(2)] complex as a reference. Dinuclear Ru(II) complexes containing the conjugated bridging ligand (BL2) showed much more intense electrochemiluminescent responses than dinuclear Ru(II) complexes with the non-conjugated bridging ligand (BL1). Among the complexes with conjugated bridging ligands, [(DTDP)(2)Ru(bpy-CC-bpy)Ru(DTDP)(2)](PF6)(4) exhibited enhanced ECL intensities as high as 3.6 times greater than that of the reference, [Ru(o-phen)(3)](PF6)(2). (C)2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.10.028

文献信息

• Physical, photophysical and structural properties of ruthenium(ii) complexes containing a tetradentate bipyridine ligand
  作者：R. A. Kirgan、P. A. Witek、C. Moore、D. P. Rillema

  DOI：10.1039/b800531a

  日期：——

  The focus of this report is the synthesis and properties of two new analogues of ruthenium(II) tris-bipyridine, a monomer and dimer. The complexes contain the ligand 6,6′-(ethan-1,2-diyl)bis-2,2′-bipyridine (O-bpy) which contains two bipyridine units bridged in the 6,6′ positions by an ethylene bridge. Crystal structures of the two complexes formulated as [Ru(bpy)(O-bpy)](PF6)2 and [(Ru(bpy)2)2(O-bpy)](PF6)4

  本报告的重点是两种新的类似物的合成和性质。 钌（II） Tris-联吡啶，单体和二聚体。配合物含有配体6,6'-（乙氧基1,2-二基）双-2,2'-联吡啶 （-），其中包含两个 联吡啶 单元在6,6'位置被一个 乙烯桥。配制为[Ru（bpy）（O-bpy）]（PF 6）2和[（Ru（bpy）2）2（O-bpy）]（PF 6）4的两个配合物的晶体结构显示出较低对称性的结构比d 3从而影响复合物的电子特性通过密度泛函理论（DFT）和时间依赖性密度泛函理论（TDDFT）的计算，证实。HOMO主要位于钌中央; LUMO将其电子密度分布在整个联吡啶单位，但在混合的O-bpy-bpy复合物中并不相等。计算的Vis /紫外线光谱 使用TDDFT方法与实验相符 光谱。对的[Ru（联吡啶）（O-联吡啶）]（PF最低躺在三重激发态6）2是3 MC导致低的发射量子产率和大氯化物 离子光饱和量子产率。
• Sannudo, E. Carolina; Grillo, Vincent A.; Yoo, Jae, Polyhedron, <hi>2001</hi>, vol. 20, p. 1269 - 1272
  作者：Sannudo, E. Carolina、Grillo, Vincent A.、Yoo, Jae、Huffman, John C.、Bollinger, John C.、et al.

  DOI：——

  日期：——
• Electrochemiluminescent dinuclear Ru(II) complexes assembled with 1,1′-(1,2-ethynediyl)- or dimethlyene-bridged bis(bipyridine) ligands: Synthesis and photophysical and electrochemical properties
  作者：Minki Kim、Chang Hoon Kang、Subong Hong、Won-Yong Lee、Byeong Hyo Kim

  DOI：10.1016/j.ica.2012.10.028

  日期：2013.1

  1,2-Di(2,2'-bipyridin-5-yl) ethane (BL1) and 1,2-di(2,2'-bipyridin-5-yl)ethyne (BL2) were synthesized as new bridging ligands and coordinated to (RuL2(acetone)(2))(PF6)(2) for the preparation of various [Ru(L)(2) (BL) Ru(L)(2)](PF6)(4)-type dinuclear ruthenium complexes (where BL = BL1, BL2 and L = bpy, o-phen, DTDP). The electrochemical redox potentials, spectroscopic properties, and relative electrochemiluminescence intensity of BL1 and BL2 were characterized and compared to those of well-known tris(1,10-phenanthroline) rutheniun(II) [Ru(o-phen)(3)](PF6)(2)] complex as a reference. Dinuclear Ru(II) complexes containing the conjugated bridging ligand (BL2) showed much more intense electrochemiluminescent responses than dinuclear Ru(II) complexes with the non-conjugated bridging ligand (BL1). Among the complexes with conjugated bridging ligands, [(DTDP)(2)Ru(bpy-CC-bpy)Ru(DTDP)(2)](PF6)(4) exhibited enhanced ECL intensities as high as 3.6 times greater than that of the reference, [Ru(o-phen)(3)](PF6)(2). (C)2012 Elsevier B. V. All rights reserved.