4-methyl-4′-[2-(2-naphthyl)ethyl]-2,2′-bipyridine

• 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-methyl-4′-[2-(2-naphthyl)ethyl]-2,2′-bipyridine
• 英文别名: bpyC2H4naph；4-Methyl-4'-(2-(2-naphthyl)ethyl]-2,2'-bipyridine；2-(4-methylpyridin-2-yl)-4-(2-naphthalen-2-ylethyl)pyridine
• 化学式: C₂₃H₂₀N₂
• 分子量: 324.425
• InChiKey: AZWQLHZSFJFVTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  4-methyl-4′-[2-(2-naphthyl)ethyl]-2,2′-bipyridine 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 [(4-methyl-4′-[2-(2-naphthyl)ethyl]-2,2′-bipyridine)2Ru(5,5′-dibromo-2,2′-bipyrimidine)](BF4)2
  参考文献：
  名称：

  合成，光物理性质，和Ru组成的新颖bichromophoric的Pd络合物的反应性（II）和-polypyridyl萘基部分†

  摘要：

  一系列带有萘基发色团的新型双发色Ru（II）配合物。2,2'-联吡啶 （py） 和 2,2'-联嘧啶（bpm）配体被合成。与钯烷基单元的络合导致双色Ru-Pd催化剂的形成。研究了新合成化合物的光化学和电化学性质。已经表明，在萘基侧基部分吸收的紫外光能有效地转移到Ru（II）中心。通过萘基单元的激发观察到金属到配体的电荷转移发光，这与通过可见光激发观察到的发光相同。带有萘基直接与萘基连接的配合物的发光寿命。py配体延长至约。1000 ns。当使用含有具有延长寿命的双发色性单元的Pd络合物作为催化剂时，与使用其他催化剂的二聚反应形成鲜明对比，观察到了在可见光或UV光照射下的苯乙烯聚合。这些结果表明形成了具有延长的激发态寿命的激发态，其优先于竞争性β-H消除步骤而促进了插入步骤。

  DOI：

  10.1039/c3dt50266j
• 作为产物：
  描述：

  4,4'-二甲基-2,2'-联吡啶 在 palladium on activated charcoal 正丁基锂 、 dehydrating agent 、 氢气 作用下， 以 四氢呋喃 为溶剂， 生成 4-methyl-4′-[2-(2-naphthyl)ethyl]-2,2′-bipyridine
  参考文献：
  名称：

  Excited-State Processes in Ruthenium(II) Bipyridine Complexes Containing Covalently Bound Arenes

  摘要：

  The photophysical properties of a series of ruthenium trisbipyridine complexes covalently linked to aromatic chromophores of the type [Ru(bpy)(2)(4-methyl-4'-(2-arylethyl)-2,2'-bipyridine)](2)(+)(ClO4)(2), where aryl = 2-naphthyl ([Ru]-naphthalene), 1-pyrenyl ([Ru]-pyrene), and 9-anthryl ([Ru]-anthracene) have been investigated at room temperature and at 77 K. The photophysical properties of these bichromophores are determined by intramolecular energy-transfer processes that are governed by the relative positions of the various singlet and tripler energy levels. As a result, fluorescence from each of the pendant aromatic chromophores is completely quenched following their photoexcitation. For [Ru]-naphthalene the initial excitation energy is localized on the [Ru]-centered (MLCT)-M-3 state, whereas for [Ru]-anthracene the energy is localized on the anthracene triplet state. Since the [Ru]-centered 3MLCT state and the lowest energy pyrene tripler state are isoenergetic, an equilibrium is established resulting in a long-lived room-temperature 3MLCT emission from [Ru]-pyrene (tau = 5.23 mu s). At 77 K dual emission is observed from this bichromophore comprising pyrene phosphorescence and (MLCT)-M-3 emission, the relative proportions of which vary with time after the laser pulse.

  DOI：

  10.1021/jp970667g

文献信息

• Excited-State Processes in Ruthenium(II) Bipyridine Complexes Containing Covalently Bound Arenes
  作者：Gerard J. Wilson、Anton Launikonis、Wolfgang H. F. Sasse、Albert W.-H. Mau

  DOI：10.1021/jp970667g

  日期：1997.7.1

  The photophysical properties of a series of ruthenium trisbipyridine complexes covalently linked to aromatic chromophores of the type [Ru(bpy)(2)(4-methyl-4'-(2-arylethyl)-2,2'-bipyridine)](2)(+)(ClO4)(2), where aryl = 2-naphthyl ([Ru]-naphthalene), 1-pyrenyl ([Ru]-pyrene), and 9-anthryl ([Ru]-anthracene) have been investigated at room temperature and at 77 K. The photophysical properties of these bichromophores are determined by intramolecular energy-transfer processes that are governed by the relative positions of the various singlet and tripler energy levels. As a result, fluorescence from each of the pendant aromatic chromophores is completely quenched following their photoexcitation. For [Ru]-naphthalene the initial excitation energy is localized on the [Ru]-centered (MLCT)-M-3 state, whereas for [Ru]-anthracene the energy is localized on the anthracene triplet state. Since the [Ru]-centered 3MLCT state and the lowest energy pyrene tripler state are isoenergetic, an equilibrium is established resulting in a long-lived room-temperature 3MLCT emission from [Ru]-pyrene (tau = 5.23 mu s). At 77 K dual emission is observed from this bichromophore comprising pyrene phosphorescence and (MLCT)-M-3 emission, the relative proportions of which vary with time after the laser pulse.
• Syntheses, photophysical properties, and reactivities of novel bichromophoric Pd complexes composed of Ru(ii)–polypyridyl and naphthyl moieties
  作者：Kei Murata、Mizuki Araki、Akiko Inagaki、Munetaka Akita

  DOI：10.1039/c3dt50266j

  日期：——

  complexes bearing a naphthyl chromophore linked with 2,2′-bipyridyl (bpy) and 2,2′-bipyrimidine (bpm) ligands were synthesized. Complexation with a Pd-alkyl unit led to the formation of bichromophoric Ru–Pd catalysts. The photochemical and electrochemical properties of the newly synthesized compounds were studied. It has been shown that the UV-light energy absorbed at the pendant naphthyl moiety is effectively

  一系列带有萘基发色团的新型双发色Ru（II）配合物。2,2'-联吡啶 （py） 和 2,2'-联嘧啶（bpm）配体被合成。与钯烷基单元的络合导致双色Ru-Pd催化剂的形成。研究了新合成化合物的光化学和电化学性质。已经表明，在萘基侧基部分吸收的紫外光能有效地转移到Ru（II）中心。通过萘基单元的激发观察到金属到配体的电荷转移发光，这与通过可见光激发观察到的发光相同。带有萘基直接与萘基连接的配合物的发光寿命。py配体延长至约。1000 ns。当使用含有具有延长寿命的双发色性单元的Pd络合物作为催化剂时，与使用其他催化剂的二聚反应形成鲜明对比，观察到了在可见光或UV光照射下的苯乙烯聚合。这些结果表明形成了具有延长的激发态寿命的激发态，其优先于竞争性β-H消除步骤而促进了插入步骤。