1,3-bis(4'-methyl-2,2'-bipyridyl-4-yl)propane | 104704-12-3

• 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: 1,3-bis(4'-methyl-2,2'-bipyridyl-4-yl)propane
• 英文别名: bis<4'-methyl<2,2'-bipyridyl>-4-yl>propane；2-(4-Methylpyridin-2-yl)-4-[3-[2-(4-methylpyridin-2-yl)pyridin-4-yl]propyl]pyridine；2-(4-methylpyridin-2-yl)-4-[3-[2-(4-methylpyridin-2-yl)pyridin-4-yl]propyl]pyridine
• CAS: 104704-12-3
• 化学式: C₂₅H₂₄N₄
• 分子量: 380.492
• InChiKey: YIFHTAGVTRIGJQ-UHFFFAOYSA-N

物化性质

• 沸点：
  560.1±45.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  1,4-二溴丁烷 、 1,3-bis(4'-methyl-2,2'-bipyridyl-4-yl)propane 生成
  参考文献：
  名称：

  Charge Separation in Donor-Chromophore-Acceptor Assemblies: Linkage and Driving Force Dependence of Photoinduced Electron Transfers

  摘要：

  A series of covalently linked Ru(bipyridine)(3)-donor-acceptor complexes was prepared where the donor-to-chromophore and acceptor-to-chromophore methylene chain lengths were varied. Time-resolved absorption studies were performed to elucidate intramolecular electron transfer rates. The electron donor in the above series is a phenothiazine moiety Linked to a bipyridine by a (-CH2-)(p), p = 3-8 chain, and the electron acceptor is an N,N'-diquaternary-2,2'-bipyridinium moiety Linked to a bipyridine by a (-CH2-)(m), m = 2, 3, 4 chain. Oxidative quenching of the Ru(bipyridine)(3) metal-to-ligand charge transfer (MLCT) state followed by phenothiazine-to-ruthenium electron transfer resulted in a long-lived charge-separated state. A wavelength-dependent excitation resulted in a slowly decaying absorption which is assigned to the excited-state phenothiazine. The magnitude of this component in the transient absorption serves as an internal standard for determining relative quantum yield for formation of the charge-separated state. Marcus inverted region behavior was observed in back electron transfer. Rate constants for electron transfer from phenothiazine to Ru(III) decreased as the length of the bridging chain increased from p = 4 to 8. Chain length independence of the back electron transfer rate in the series of complexes with varied chromophore-acceptor distances (m = 2, 3, and 4) suggests the formation of an association complex during oxidative quenching of MLCT state and argues against a sigma-bond superexchange pathway for back electron transfer.

  DOI：

  10.1021/j100017a038
• 作为产物：
  描述：

  4,4'-二甲基-2,2'-联吡啶 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 1,3-bis(4'-methyl-2,2'-bipyridyl-4-yl)propane
  参考文献：
  名称：

  二-和三-亚甲基连接的三（2,2'-联吡啶）钌（II）复合二聚体的合成和发光特性。地激发态相互作用

  摘要：

  合成了二和三亚甲基连接的 Ru(bpy)32+ 配合物 2。将2的发光性能与其组分单体的发光性能进行了比较。在激发的 2 系统中，未观察到导致淬灭增强或形成新的三重态准分子的分子内相互作用。

  DOI：

  10.1246/cl.1986.1209

文献信息

• Intramolecular Energy Transfer in Covalently Linked Polypyridine Ruthenium(II)/Osmium(II) Binuclear Complexes. Ru(II)(bpy)₂Mebpy– (CH₂)<i>_n</i>–MebpyOs(II)(bpy)₂(<i>n</i>=2, 3, 5, and 7)
  作者：Masaoki Furue、Toshiyuki Yoshidzumi、Shuichi Kinoshita、Takashi Kushida、Shun-ichi Nozakura、Mikiharu Kamachi

  DOI：10.1246/bcsj.64.1632

  日期：1991.5

  heterobinuclear complexes of polypyridine ruthenium(II)/osmium(II) complex Ru(II)(bpy)2Mebpy–(CH2)n–MebpyOs(II)(bpy)2(bpy=2,2′-bipyridine and n=2, 3, 5, and 7), 1, was prepared. The photophysical behavior was examined in various solvents. The emission spectra of 1 (excitation wavelength: 455nm) showed a nearly complete quenching of RuII→π*(bpy) metal-to-ligand charge transfer (MLCT) emission and the enhancement of

  聚吡啶钌(II)/锇(II)配合物Ru(II)(bpy)2Mebpy-(CH2)n-MebpyOs(II)(bpy)2(bpy=2,2')的一系列新型多亚甲基连接的异双核配合物-联吡啶和 n=2、3、5 和 7), 1, 被制备。在各种溶剂中检查光物理行为。1的发射光谱（激发波长：455nm）显示RuII→π*（bpy）金属-配体电荷转移（MLCT）发射几乎完全猝灭，OsII→π*（bpy）MLCT发射增强。通过时间相关的单光子计数方法测量的发光寿命提供了证据，表明分子内能量转移是观察到的发射猝灭的重要途径。乙醇中分子内能量转移的速率常数分别为 5.3×108、3.3×108、1.3×108 和 1.0×108s−1（n=2、3、5 和 7）。发现它们与两个复合物的中心到中心距离的倒数六次方成正比。该机制是根据 Forster（偶极子...
• Ru(<scp>ii</scp>)–Re(<scp>i</scp>) binuclear photocatalysts connected by –CH₂XCH₂– (X = O, S, CH₂) for CO₂ reduction
  作者：Eishiro Kato、Hiroyuki Takeda、Kazuhide Koike、Kei Ohkubo、Osamu Ishitani

  DOI：10.1039/c4sc03710c

  日期：——

  developed Ru(II)–Re(I) supramolecular photocatalysts in which each metal complex unit is connected by a –CH2XCH2– (X = O, S, CH2) chain. The photocatalyst with X = O exhibited the best photocatalytic efficiency for CO2 reduction in the reported systems using a NAD(P)H model compound as an electron donor because the introduced oxygen atom strengthened the oxidation power of the Ru photosensitizer unit in the

  我们开发了Ru（II）-Re（I）超分子光催化剂，其中每个金属络合物单元通过–CH 2 XCH 2 –（X = O，S，CH 2）链连接。X = O的光催化剂在使用NAD（P）H模型化合物作为电子供体的已报道系统中表现出最佳的CO 2还原光催化效率，因为引入的氧原子增强了Ru光敏剂单元在激发态下的氧化能力并加速电子从单电子还原Ru光敏剂单元到Re的转移催化剂单元。相反，由于超分子结构分裂成单核络合物，因此X = S的光催化剂的催化能力迅速降低。首次研究了涉及这些超分子光催化剂的有效光催化反应的详细机理。
• Electrochemical Studies of Structurally Related Triply-Bridged Dinuclear Tris(bipyridine)iron(II) Complexes: An Electrostatic Model for Site-Site Interaction
  作者：Suzanne Ferrere、C. Michael Elliott

  DOI：10.1021/ic00127a020

  日期：1995.11

  The structures and electrochemical behavior of a series of symmetric dinuclear complexes in which two iron centers are bridged by three bis[4-(4'-methyl-2,2'-bipyridinyl)]alkane ligands are presented. Square wave voltammetry was used to characterize the extent of interaction between the metal-centered halves. Because the saturated linkages preclude significant electron delocalization the observed interaction is concluded to be almost purely Coulombic in nature. Furthermore, molecular modeling and X-ray crystallographic data confirm that the iron-iron separation in the complex containing three methylenes in the linkages is nearly identical to the iron-iron separation in the complex containing two methylenes in the linkages. Using a simple electrostatic model and employing structural parameters obtained from X-ray data and molecular modeling, the electrochemical trends within the series are interpreted.
• Synthesis and Luminescence Properties of Di- and Tri-methylene Linked Tris(2,2′-bipyridine)ruthenium(II) Complex Dimers. Ground-Excited State Interaction
  作者：Masaoki Furue、Noritaka Kuroda、Shun-ichi Nozakura

  DOI：10.1246/cl.1986.1209

  日期：1986.7.5

  Di- and tri-methylene-linked Ru(bpy)32+ complexes 2 were synthesized. The luminescence properties of 2 were compared with those of its component monomer. In the excited 2 systems, the intramolecular interaction leading to the enhanced quenching or the formation of a new triplet excimer was not observed.

  合成了二和三亚甲基连接的 Ru(bpy)32+ 配合物 2。将2的发光性能与其组分单体的发光性能进行了比较。在激发的 2 系统中，未观察到导致淬灭增强或形成新的三重态准分子的分子内相互作用。
• Charge Separation in Donor-Chromophore-Acceptor Assemblies: Linkage and Driving Force Dependence of Photoinduced Electron Transfers
  作者：S. L. Larson、C. Michael Elliott、D. F. Kelley

  DOI：10.1021/j100017a038

  日期：1995.4

  A series of covalently linked Ru(bipyridine)(3)-donor-acceptor complexes was prepared where the donor-to-chromophore and acceptor-to-chromophore methylene chain lengths were varied. Time-resolved absorption studies were performed to elucidate intramolecular electron transfer rates. The electron donor in the above series is a phenothiazine moiety Linked to a bipyridine by a (-CH2-)(p), p = 3-8 chain, and the electron acceptor is an N,N'-diquaternary-2,2'-bipyridinium moiety Linked to a bipyridine by a (-CH2-)(m), m = 2, 3, 4 chain. Oxidative quenching of the Ru(bipyridine)(3) metal-to-ligand charge transfer (MLCT) state followed by phenothiazine-to-ruthenium electron transfer resulted in a long-lived charge-separated state. A wavelength-dependent excitation resulted in a slowly decaying absorption which is assigned to the excited-state phenothiazine. The magnitude of this component in the transient absorption serves as an internal standard for determining relative quantum yield for formation of the charge-separated state. Marcus inverted region behavior was observed in back electron transfer. Rate constants for electron transfer from phenothiazine to Ru(III) decreased as the length of the bridging chain increased from p = 4 to 8. Chain length independence of the back electron transfer rate in the series of complexes with varied chromophore-acceptor distances (m = 2, 3, and 4) suggests the formation of an association complex during oxidative quenching of MLCT state and argues against a sigma-bond superexchange pathway for back electron transfer.