3,10-di(10H-phenothiazin-10-yl)perylene | 252755-37-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3,10-di(10H-phenothiazin-10-yl)perylene
• 英文别名: 10-(10-Phenothiazin-10-ylperylen-3-yl)phenothiazine
• CAS: 252755-37-6
• 化学式: C₄₄H₂₆N₂S₂
• 分子量: 646.836
• InChiKey: BEVFVKBXEBOPNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.5
• 重原子数：
  48
• 可旋转键数：
  2
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 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.