methyl-4'-(4-(N-phenothiazinato)pentyl)-2,2'-bipyridine | 165749-10-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: methyl-4'-(4-(N-phenothiazinato)pentyl)-2,2'-bipyridine
• 英文别名: 4-methyl-4'-(4-(N-phenothiazinato)pentyl)-2,2'-bipyridine；PTZpbpy；10-[5-[2-(4-Methylpyridin-2-yl)pyridin-4-yl]pentyl]phenothiazine；10-[5-[2-(4-methylpyridin-2-yl)pyridin-4-yl]pentyl]phenothiazine
• CAS: 165749-10-0
• 化学式: C₂₈H₂₇N₃S
• 分子量: 437.608
• InChiKey: ZYPXZYOEELMWDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  54.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dichlorotetrakis(dimethylsulfoxide)ruthenium(II) 、 methyl-4'-(4-(N-phenothiazinato)pentyl)-2,2'-bipyridine 在 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 bis(4-methyl-4'-(4-(N-phenothiazinato)pentyl)-2,2'-bipyridine)dichlororuthenium(II)
  参考文献：
  名称：

  包含多嗪桥连配体 2,3-双（2-吡啶基）吡嗪的供体-发色团复合物

  摘要：

  摘要 络合物 [(PTZpbpy) 2 Ru(dpp)](PF 6 ) 2 将吩噻嗪衍生的电子供体与具有多嗪桥连配体 dpp 的钌络合物偶联 (PTZpbpy = 4-methyl-4'-(4-( N - phenothiazinato)pentyl)-2,2'-bipyridine, dpp = 2,3-bis(2-pyridyl)pyrazine) 已被合成，并阐明了氧化还原、光谱和激发态特性。在耦合电子供体系统中，Ru(dπ) → dpp(π ∗ ) 3 MLCT 态的发射强度淬灭了类似系统 [(bpy) 2 Ru(dpp)](PF 6 ) 的 94% 2 (bpy = 2,2'-联吡啶) 缺少耦合电子供体。将供体-发色团单元与桥接配体偶联将允许分子结构扩展以形成包含共价连接的电子供体的复杂分子组装体。

  DOI：

  10.1016/j.inoche.2007.06.019
• 作为产物：
  描述：

  吩噻嗪 、 4-(5-bromopentyl)-4'-methyl-2,2'-bipyridine 在 sodium hydride 作用下， 生成 methyl-4'-(4-(N-phenothiazinato)pentyl)-2,2'-bipyridine
  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

文献信息

• 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.
• A donor–chromophore complex containing the polyazine bridging ligand 2,3-bis(2-pyridyl)pyrazine
  作者：Shamindri M. Arachchige、Karen J. Brewer

  DOI：10.1016/j.inoche.2007.06.019

  日期：2007.10

  Abstract The complex [(PTZpbpy) 2 Ru(dpp)](PF 6 ) 2 coupling a phenothiazine derived electron donor to a ruthenium complex with a polyazine bridging ligand dpp (PTZpbpy = 4-methyl-4′-(4-( N -phenothiazinato)pentyl)-2,2′-bipyridine, dpp = 2,3-bis(2-pyridyl)pyrazine) has been synthesized and the redox, spectroscopic, and excited state properties elucidated. In the coupled electron donor system, the emission

  摘要 络合物 [(PTZpbpy) 2 Ru(dpp)](PF 6 ) 2 将吩噻嗪衍生的电子供体与具有多嗪桥连配体 dpp 的钌络合物偶联 (PTZpbpy = 4-methyl-4'-(4-( N - phenothiazinato)pentyl)-2,2'-bipyridine, dpp = 2,3-bis(2-pyridyl)pyrazine) 已被合成，并阐明了氧化还原、光谱和激发态特性。在耦合电子供体系统中，Ru(dπ) → dpp(π ∗ ) 3 MLCT 态的发射强度淬灭了类似系统 [(bpy) 2 Ru(dpp)](PF 6 ) 的 94% 2 (bpy = 2,2'-联吡啶) 缺少耦合电子供体。将供体-发色团单元与桥接配体偶联将允许分子结构扩展以形成包含共价连接的电子供体的复杂分子组装体。