4-Methyl-4'-(2-hydroxyethylpyrenyl)-2,2'-bipyridine | 253325-69-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 4-Methyl-4'-(2-hydroxyethylpyrenyl)-2,2'-bipyridine
• 英文别名: 2-[2-(4-Methylpyridin-2-yl)pyridin-4-yl]-1-pyren-1-ylethanol；2-[2-(4-methylpyridin-2-yl)pyridin-4-yl]-1-pyren-1-ylethanol
• CAS: 253325-69-8
• 化学式: C₂₉H₂₂N₂O
• 分子量: 414.506
• InChiKey: SSZPSGQKHFPSNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Methyl-4'-(2-hydroxyethylpyrenyl)-2,2'-bipyridine 在 dehydrating agent 作用下， 生成 4-Methyl-4'-((E)-2-pyren-1-yl-vinyl)-[2,2']bipyridinyl
  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
• 作为产物：
  描述：

  4,4'-二甲基-2,2'-联吡啶 、 1-芘甲醛 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以38%的产率得到4-Methyl-4'-(2-hydroxyethylpyrenyl)-2,2'-bipyridine
  参考文献：
  名称：

  Intramolecular Singlet and Triplet Energy Transfer in a Ruthenium(II) Diimine Complex Containing Multiple Pyrenyl Chromophores

  摘要：

  We report the synthesis and the photophysical properties of UV light-harvesting arrays constructed around a [Ru(bpy)(3)](2+) core (bpy = 2,2'-bipyridine) bearing one and three pyrenyl units in the periphery. The free ligand containing the pyrenyl unit, 4-methyl-4'-(2-hydroxyethylpyrenyl)-2,2'-bipyridine, displays an intense emission band centered near 400 nm with a lifetime of 264 ns, characteristic of singlet pyrene emission.;The complexes [Ru(dmb)(2)(4-methyl-4'-(2-hydroxyethylpyrenyl)-2,2'-bipyridine)](PF6)(2), where dmb is 4,4'-dimethyl-2,2'-bipyridine, and [Ru(4-methyl-4'- (2-hydroxyethylpyrenyl) -2,2'-bipyridine)(3)] (PF6)(2) exhibit visible emission characteristic of the [Ru(bpy)(3)](2+) unit, regardless of excitation wavelength. The singlet emission from the pyrene chromophores is almost quantitatively quenched by the metal-to-ligand charge transfer (MLCT) states of each respective Ru(TI) complex resulting in the observation of sensitized MLCT-based emission. On account of the energetic proximity between the (MLCT)-M-3 states and the (3)pyrene states, a long-lived (MLCT)-M-3 emission is observed which decays with the same first-order Lifetime as the pyrene triplet states in deaerated CH3CN. In deaerated CH3CN, the bichromophoric system displays a lifetime of 2.96 mu s, whereas the tetrad complex exhibits a lifetime of 9.0 mu s. The results are indicative of excited-state equilibrium between the (MLCT)-M-3 and (3)pyrene states. Our findings demonstrate rapid and efficient singlet-singlet energy transfer through the antenna effect whereas the reversible triplet-triplet energy transfer processes help sustain long-lived MLCT excited states.

  DOI：

  10.1021/jp992983w

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.
• Intramolecular Singlet and Triplet Energy Transfer in a Ruthenium(II) Diimine Complex Containing Multiple Pyrenyl Chromophores
  作者：Daniel S. Tyson、Felix N. Castellano

  DOI：10.1021/jp992983w

  日期：1999.12.1

  We report the synthesis and the photophysical properties of UV light-harvesting arrays constructed around a [Ru(bpy)(3)](2+) core (bpy = 2,2'-bipyridine) bearing one and three pyrenyl units in the periphery. The free ligand containing the pyrenyl unit, 4-methyl-4'-(2-hydroxyethylpyrenyl)-2,2'-bipyridine, displays an intense emission band centered near 400 nm with a lifetime of 264 ns, characteristic of singlet pyrene emission.;The complexes [Ru(dmb)(2)(4-methyl-4'-(2-hydroxyethylpyrenyl)-2,2'-bipyridine)](PF6)(2), where dmb is 4,4'-dimethyl-2,2'-bipyridine, and [Ru(4-methyl-4'- (2-hydroxyethylpyrenyl) -2,2'-bipyridine)(3)] (PF6)(2) exhibit visible emission characteristic of the [Ru(bpy)(3)](2+) unit, regardless of excitation wavelength. The singlet emission from the pyrene chromophores is almost quantitatively quenched by the metal-to-ligand charge transfer (MLCT) states of each respective Ru(TI) complex resulting in the observation of sensitized MLCT-based emission. On account of the energetic proximity between the (MLCT)-M-3 states and the (3)pyrene states, a long-lived (MLCT)-M-3 emission is observed which decays with the same first-order Lifetime as the pyrene triplet states in deaerated CH3CN. In deaerated CH3CN, the bichromophoric system displays a lifetime of 2.96 mu s, whereas the tetrad complex exhibits a lifetime of 9.0 mu s. The results are indicative of excited-state equilibrium between the (MLCT)-M-3 and (3)pyrene states. Our findings demonstrate rapid and efficient singlet-singlet energy transfer through the antenna effect whereas the reversible triplet-triplet energy transfer processes help sustain long-lived MLCT excited states.