methyl-4'-(4-(N-phenothiazinato)butyl)-2,2'-bipyridine | 136847-75-1

• 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)butyl)-2,2'-bipyridine
• 英文别名: 4-methyl-4'-(4-(N-phenothiazinato)butyl)-2,2'-bipyridine；10-[4-[2-(4-Methylpyridin-2-yl)pyridin-4-yl]butyl]phenothiazine；10-[4-[2-(4-methylpyridin-2-yl)pyridin-4-yl]butyl]phenothiazine
• CAS: 136847-75-1
• 化学式: C₂₇H₂₅N₃S
• 分子量: 423.582
• InChiKey: UVUSFBUXLFUYCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 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)butyl)-2,2'-bipyridine 以 N,N-二甲基甲酰胺 为溶剂， 生成 bis(4-methyl-4'-(4-(N-phenothiazinato)butyl)-2,2'-bipyridine)dichlororuthenium(II)
  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：

  吩噻嗪 、 4-(4-bromobutyl)-4'-methyl-2,2'-bipyridine 在 sodium hydride 作用下， 生成 methyl-4'-(4-(N-phenothiazinato)butyl)-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 linked tris(2,2'-(bipyridine)-ruthenium donor-acceptor complexes
  作者：L. F. Cooley、S. L. Larson、C. M. Elliott、D. F. Kelley

  DOI：10.1021/j100179a034

  日期：1991.12

  Time-resolved emission studies have been performed on a series of covalently linked Ru(bipyridine)3-donor-acceptor complexes. In these complexes the donor is a phenothiazine moiety linked to a bipyridine by a (-CH2-)4 chain, and the acceptor is an N,N'-diquaternary-2,2'-bipyridinium moiety, linked to a bipyridine by a (-CH2-)2 chain. Excitation to the Ru(bipyridine)3 metal-to-ligand charge-transfer (MLCT) state leads to a long-lived charge-separated state. The results are compared to those obtained in the analogous Ru(bipyridine)3-acceptor complexes. The results can be understood in terms of a model in which the initial step in the formation of the charge-separated state is oxidative quenching of the MLCT state, followed by phenothiazine to ruthenium electron transfer. The charge separation occurs efficiently in dichloroethane, but not in acetonitrile. This result is discussed in terms of the relative rates of acceptor-to-ruthenium reverse electron transfer in the two solvents.
• 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.