3-bromo-7-cyano-10-hexyl-10H-phenothiazine | 1258422-45-5

• 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: 3-bromo-7-cyano-10-hexyl-10H-phenothiazine
• 英文别名: 7-Bromo-10-hexylphenothiazine-3-carbonitrile
• CAS: 1258422-45-5
• 化学式: C₁₉H₁₉BrN₂S
• 分子量: 387.343
• InChiKey: FPBGMDIAPAEGKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9,10-蒽二硼酸二频哪酯 、 3-bromo-7-cyano-10-hexyl-10H-phenothiazine 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 9.0h， 以51%的产率得到7,7'-(anthracene-9,10-diyl)bis(10-hexyl-10H-phenothiazine-3-carbonitrile)
  参考文献：
  名称：

  Luminescent, Redox-Active Diphenothiazine Dumbbells Expanded by Conjugated Arenes and Heteroarenes

  摘要：

  Dumbbell-shaped diphenothiazines bridged by conjugatively linked (hetero)aromatic moieties were synthesized in a modular fashion by Suzuki-Miyaura coupling in good yields. The electronic structure was studied by DFT computations, determining the geometry optimized lowest energy conformers and scrutinizing the Kohn-Sham FMOs. The torsional deviation from coplanarity is predominantly influencing the electronic structure, i.e., by deviation from ideal overlap and maximal electron transmission. The reversible oxidation potentials assigned to the phenothiazinyl electrophores in most cases can thereby be qualitatively rationalized. All dumbbell-shaped diphenothiazines are strongly luminescent, which can be attributed to extended pi-electron conjugation with considerable excited state electronic coupling as a consequence of large structural and electronic distributional changes upon photoexcitation.

  DOI：

  10.1021/jo101997t
• 作为产物：
  描述：

  3-bromo-10-hexyl-10H-phenothiazine 在 N-甲基吡咯烷酮 、 1,1'-双(二苯基膦)二茂铁 、 溴 、 palladium diacetate 、 sodium carbonate 、 溶剂黄146 作用下， 反应 32.0h， 生成 3-bromo-7-cyano-10-hexyl-10H-phenothiazine
  参考文献：
  名称：

  Luminescent, Redox-Active Diphenothiazine Dumbbells Expanded by Conjugated Arenes and Heteroarenes

  摘要：

  Dumbbell-shaped diphenothiazines bridged by conjugatively linked (hetero)aromatic moieties were synthesized in a modular fashion by Suzuki-Miyaura coupling in good yields. The electronic structure was studied by DFT computations, determining the geometry optimized lowest energy conformers and scrutinizing the Kohn-Sham FMOs. The torsional deviation from coplanarity is predominantly influencing the electronic structure, i.e., by deviation from ideal overlap and maximal electron transmission. The reversible oxidation potentials assigned to the phenothiazinyl electrophores in most cases can thereby be qualitatively rationalized. All dumbbell-shaped diphenothiazines are strongly luminescent, which can be attributed to extended pi-electron conjugation with considerable excited state electronic coupling as a consequence of large structural and electronic distributional changes upon photoexcitation.

  DOI：

  10.1021/jo101997t

文献信息

• Luminescent, Redox-Active Diphenothiazine Dumbbells Expanded by Conjugated Arenes and Heteroarenes
  作者：Martina Hauck、Raluca Turdean、Karin Memminger、Jan Schönhaber、Frank Rominger、T. J. J. Müller

  DOI：10.1021/jo101997t

  日期：2010.12.17

  Dumbbell-shaped diphenothiazines bridged by conjugatively linked (hetero)aromatic moieties were synthesized in a modular fashion by Suzuki-Miyaura coupling in good yields. The electronic structure was studied by DFT computations, determining the geometry optimized lowest energy conformers and scrutinizing the Kohn-Sham FMOs. The torsional deviation from coplanarity is predominantly influencing the electronic structure, i.e., by deviation from ideal overlap and maximal electron transmission. The reversible oxidation potentials assigned to the phenothiazinyl electrophores in most cases can thereby be qualitatively rationalized. All dumbbell-shaped diphenothiazines are strongly luminescent, which can be attributed to extended pi-electron conjugation with considerable excited state electronic coupling as a consequence of large structural and electronic distributional changes upon photoexcitation.