10-(perylen-3-yl)-10H-phenothiazine | 1012068-11-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 10-(perylen-3-yl)-10H-phenothiazine
• 英文别名: 10-Perylen-3-ylphenothiazine
• CAS: 1012068-11-9
• 化学式: C₃₂H₁₉NS
• 分子量: 449.576
• InChiKey: SMJROZZAZWXFKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  34
• 可旋转键数：
  1
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  10-(perylen-3-yl)-10H-phenothiazine 在 nitrosyl hexafluorophosphate 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  紧凑正交苝 - 吩噻嗪或 -吩恶嗪三联体中的有效对称破缺自旋轨道电荷转移诱导的系统间交叉和延迟荧光的观察

  摘要：

  通过连接两个相同的电子供体单元，即吩噻嗪 (PTZ, Pery-2PTZ ) 和吩恶嗪 (PXZ, Pery-2PXZ ) 来合成基于苝的正交三元组，以研究对称破坏自旋轨道电荷转移系统间交叉 (SOCT-ISC) ）。ISC 效率高度依赖于溶剂极性，在中等极性溶剂中最大（单线态氧量子产率Φ Δ = 46-70%），并且高于先前报道的Pery-PTZ / Pery-PXZ二元组（Φ Δ= DCM 中的 20–60%）。飞秒瞬态吸收光谱证实了这些紧凑的电子供体-受体-供体 (D-A-D) 三元组中的对称破缺电荷转移 (SBCT) 过程，其中电荷分离 (CS) 发生在ca. 0.17-0.27 ps，其次是 SOCT-ISC 在 1.0-2.6 ns 内，这比先前报道的模拟二元组（CS，0.25-0.49 ps 和 ISC，0.99-5.98 ns）更快。在 DCM 溶液 ( τ T = 359

  DOI：

  10.1039/d2tc01640k
• 作为产物：
  描述：

  吩噻嗪 、 3,10-dibromoperylene 在 tris-(dibenzylideneacetone)dipalladium(0) potassium tert-butylate 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 1,4-二氧六环 为溶剂， 反应 14.0h， 以31%的产率得到3,10-di(10H-phenothiazin-10-yl)perylene
  参考文献：
  名称：

  Synthesis and Electronic Properties of Sterically Demanding N-Arylphenothiazines and Unexpected Buchwald−Hartwig Aminations

  摘要：

  [Graphics]Phenothiazine is coupled under Buchwald - Hartwig conditions with bromo anthracenes and perylene as substrates to give phenothiazine-anthracene and phenothiazine-perylene dyads and triads. Investigation of the electronic properties of these sterically demanding N-aryl phenothiazines by absorption and emission spectroscopy, cyclic voltammetry, and DFT calculations revealed that the individual chromophores are decoupled in the electronic ground state but show unique electronic communication in the excited state. For the anthracenyl-bridged diphenothiazine an intense electronic coupling of the phenothiazinyl units is detected upon oxidation. Besides, attempts to synthesize phenothiazine compounds with even more sterically demanding aryl substituents in the 10-position under N-arylation conditions gave rise to the formation of quite unexpected products of arylation and/or oxidative coupling. The folding angle of the phenothiazine in a consanguineous series correlates well with the first oxidation potential.

  DOI：

  10.1021/jo702389v

文献信息

• Synthesis and Electronic Properties of Sterically Demanding <i>N-</i>Arylphenothiazines and Unexpected Buchwald−Hartwig Aminations
  作者：Adam W. Franz、Frank Rominger、Thomas J. J. Müller

  DOI：10.1021/jo702389v

  日期：2008.3.1

  [Graphics]Phenothiazine is coupled under Buchwald - Hartwig conditions with bromo anthracenes and perylene as substrates to give phenothiazine-anthracene and phenothiazine-perylene dyads and triads. Investigation of the electronic properties of these sterically demanding N-aryl phenothiazines by absorption and emission spectroscopy, cyclic voltammetry, and DFT calculations revealed that the individual chromophores are decoupled in the electronic ground state but show unique electronic communication in the excited state. For the anthracenyl-bridged diphenothiazine an intense electronic coupling of the phenothiazinyl units is detected upon oxidation. Besides, attempts to synthesize phenothiazine compounds with even more sterically demanding aryl substituents in the 10-position under N-arylation conditions gave rise to the formation of quite unexpected products of arylation and/or oxidative coupling. The folding angle of the phenothiazine in a consanguineous series correlates well with the first oxidation potential.
• Efficient symmetry breaking spin–orbit charge transfer-induced intersystem crossing in compact orthogonal perylene-phenothiazine or -phenoxazine triads and observation of the delayed fluorescence
  作者：Muhammad Imran、Junhong Pang、Jianzhang Zhao、Ming-De Li

  DOI：10.1039/d2tc01640k

  日期：——

  state of the triad in polar solvent was confirmed by an intermolecular photosensitizing method. Solvent-dependent, triplet–triplet annihilation (TTA)-based p-type delayed fluorescence was observed for the triads (luminescence lifetime = 114 μs under the specific experimental conditions). The triads were also used as efficient triplet photosensitizers for the generation of delayed fluorescence with solvent

  通过连接两个相同的电子供体单元，即吩噻嗪 (PTZ, Pery-2PTZ ) 和吩恶嗪 (PXZ, Pery-2PXZ ) 来合成基于苝的正交三元组，以研究对称破坏自旋轨道电荷转移系统间交叉 (SOCT-ISC) ）。ISC 效率高度依赖于溶剂极性，在中等极性溶剂中最大（单线态氧量子产率Φ Δ = 46-70%），并且高于先前报道的Pery-PTZ / Pery-PXZ二元组（Φ Δ= DCM 中的 20–60%）。飞秒瞬态吸收光谱证实了这些紧凑的电子供体-受体-供体 (D-A-D) 三元组中的对称破缺电荷转移 (SBCT) 过程，其中电荷分离 (CS) 发生在ca. 0.17-0.27 ps，其次是 SOCT-ISC 在 1.0-2.6 ns 内，这比先前报道的模拟二元组（CS，0.25-0.49 ps 和 ISC，0.99-5.98 ns）更快。在 DCM 溶液 ( τ T = 359