4-methyl-4'-[2-(1-pyrenyl)ethyl]-2,2'-bipyridine | 500615-70-3

• 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-(1-pyrenyl)ethyl]-2,2'-bipyridine
• 英文别名: 4-methyl-4'-[2-(pyren-1-yl)ethyl]-2,2'-bipyridine；4-methyl-4’-[2-(1-pyrenyl)ethyl]-2,2’-bipyridyl；Pyrbpy；2-(4-Methylpyridin-2-yl)-4-(2-pyren-1-ylethyl)pyridine；2-(4-methylpyridin-2-yl)-4-(2-pyren-1-ylethyl)pyridine
• CAS: 500615-70-3
• 化学式: C₂₉H₂₂N₂
• 分子量: 398.507
• InChiKey: TUWZUGHKYBTKJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  31
• 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：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (tetrabutylammonium)4[Ru(CN)6] 、 4-methyl-4'-[2-(1-pyrenyl)ethyl]-2,2'-bipyridine 在 H₂SO₄ 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 以60%的产率得到(TBA)2[Ru(Pyrbpy)(CN)4]
  参考文献：
  名称：

  双发色体系中分子内能量转移的溶剂转换：（2,2'-联吡啶）四氰基尿酸酯（II）/吡啶基络合物的光物理。

  摘要：

  超分子系统[Ru（Pyr（n）bpy）（CN）（4）]（2-）（n = 1，2），其中一个和两个pyr烯单元通过两个亚甲基桥连接到[Ru（bpy） ）（CN）（4）]（2-）发色团已合成。已在水，甲醇和乙腈中研究了这些系统的光物理性质，这些系统包含高度溶剂化的金属络合物部分。在所有溶剂中，迅速，有效的单重态-单重态能量转移都发生在从moiety到无机部分的过程中。另一方面，三重态水平下的能量转移显着地取决于溶剂。在水中，Ru基发色团的金属至配体电荷转移（MLCT）发射被完全淬灭，并且在超快光谱学中检测到快速（对于n = 1为200 ps）不可逆的三重态能量转移至to单元。在乙腈中 the基发色团的存在实际上不影响MLCT的发射，这意味着不存在任何组分间三重态能量转移。在甲醇中，三重态能量转移会导致激发的发色团之间达到平衡，从而大大延长了MLCT的寿命。对[Ru（Pyr（n）bpy）（CN）

  DOI：

  10.1021/ic034185x
• 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-(1-pyrenyl)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

• Direct Observation of Reversible Electronic Energy Transfer Involving an Iridium Center
  作者：Sergey A. Denisov、Yanouk Cudré、Peter Verwilst、Gediminas Jonusauskas、Marta Marín-Suárez、Jorge Fernando Fernández-Sánchez、Etienne Baranoff、Nathan D. McClenaghan

  DOI：10.1021/ic4030712

  日期：2014.3.3

  the pendant pyrene were studied using steady-state and time-resolved spectroscopies. Reversible electronic energy transfer (REET) is demonstrated, uniquely with an emissive cyclometalated iridium center and an adjacent organic chromophore. After excited-state equilibration is established (5 ns) as a result of REET, extremely long luminescence lifetimes of up to 225 μs result, compared to 8.3 μs for the

  报道了一种环金属化铱配合物，其中核心配合物包含作为主要配体的萘基吡啶，辅助的 2,2'-联吡啶配体通过短烷基桥连接到芘单元。为了获得具有令人满意纯度的配合物，有必要将标准合成（辅助配体与氯桥接铱二聚体的直接反应）修改为利用中间体四甲基庚醇盐基配合物的方法，该配合物经过酸促进去除辅助配体和随后的络合。使用稳态和时间分辨光谱研究了双发色复合物和没有悬垂芘的模型复合物的光物理行为。可逆电子能量转移（REET）被证明，独特的发光环金属化铱中心和相邻的有机发色团。在 REET 建立激发态平衡 (5 ns) 后，产生高达 225 μs 的极长发光寿命，而模型复合体的发光寿命为 8.3 μs，而不会降低发射量子产率。因此，在溶液和聚合物基质中都观察到了非常高的氧敏感性。
• Visible-light-driven Electron Transport across Vesicle Membrane Sensitized by Cationic Iridium Complexes
  作者：Ryo Aboshi、Shin-ya Takizawa、Shigeru Murata

  DOI：10.1246/cl.141203

  日期：2015.4.5

  A bichromophoric cationic iridium complex having a pyrene-substituted bipyridine ligand acts as a sensitizer for visible-light-driven electron transport from ascorbate (an electron donor) to methyl viologen (an electron acceptor) across hydrophobic vesicle membrane without any additional components acting as electron carriers.

  一种具有芘取代双吡啶配体的双色阳离子铱络合物，可作为可见光驱动的电子传输的敏化剂，在疏水性囊泡膜上从抗坏血酸盐（电子供体）向甲基紫精（电子受体）传输电子，无需任何其他成分作为电子载体。
• Towards ruthenium(ii) polypyridine complexes with prolonged and predetermined excited state lifetimesElectronic supplementary information (ESI) available: synthesis of the new ligands bpy–pyr and pyr–bpy–pyr and of their ruthenium compounds. See http://www.rsc.org/suppdata/cc/b1/b110291e/
  作者：Nathan D. McClenaghan、Francesco Barigelletti、Béatrice Maubert、Sebastiano Campagna

  DOI：10.1039/b110291e

  日期：2002.3.7

  The excited state lifetime of a Ru(bpy)3-motif is linearly related to the number of appended pyrenyl chromophores, but independent of connectivity; values for nine complexes range from 0.8 to 18.1 microseconds.

  Ru（bpy）3-基团的激发态寿命与附着的pyr基发色团的数量成线性关系，但与连接性无关。九种复合物的值范围从0.8到18.1微秒。
• ——
  作者：Nathan D. McClenaghan、Frédérique Loiseau、Fausto Puntoriero、Scolastica Serroni、Sebastiano Campagna

  DOI：10.1039/b109068b

  日期：2001.12.19

  A new tetranuclear heterometallic complex carrying six pyrenyl chromophores at the periphery has been prepared: this species is an example of a new class of light-harvesting metal dendrimer, in which multinuclear metal dendrimers are surrounded by additional purely organic chromophores.
• 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.