1-(10-methylphenothiazin-3-yl)-N-[4-[9-[4-[(10-methylphenothiazin-3-yl)methylideneamino]phenyl]fluoren-9-yl]phenyl]methanimine | 1417424-41-9

• 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: 1-(10-methylphenothiazin-3-yl)-N-[4-[9-[4-[(10-methylphenothiazin-3-yl)methylideneamino]phenyl]fluoren-9-yl]phenyl]methanimine
• CAS: 1417424-41-9
• 化学式: C₅₃H₃₈N₄S₂
• 分子量: 795.044
• InChiKey: CRARVJCVDJQMNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.9
• 重原子数：
  59
• 可旋转键数：
  6
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  81.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  10-甲基-10H-吩噻嗪-3-甲醛 、 9,9-双(4-氨基苯基)芴 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以94%的产率得到1-(10-methylphenothiazin-3-yl)-N-[4-[9-[4-[(10-methylphenothiazin-3-yl)methylideneamino]phenyl]fluoren-9-yl]phenyl]methanimine
  参考文献：
  名称：

  Novel luminescent phenothiazine-based Schiff bases with tuned morphology. Synthesis, structure, photophysical and thermotropic characterization

  摘要：

  New Schiff base dimers based on phenothiazine heterocycle have been obtained with high yield and purity by condensation of 3-formyl-10-methyl-phenothiazine with various amines. The structural characterization was performed by elemental analysis, FTIR, 1D and 2D NMR spectroscopy and single crystal and powder wide angle X-ray diffraction. The obtained compounds have high thermal stability and some of them self-assemble into cubic mesophase and form stable molecular glass. The thermotropic study performed by polarized optical microscopy and differential scanning calorimetry revealed the possibility to control the compound morphology by thermal annealing and blending miscible components. The photophysical characterization indicates green light emission, with good absolute fluorescence quantum yield, large Stokes shift and high purity and fully saturated color. The special thermal behavior and photophysical properties appear to be significantly dependent on the special supramolecular architecture generated by the hockey-stick shape of the imino-phenothiazine mesogenic core.Collectively, the properties of these azomethines provide a starting point for new compounds with great advantages for optoelectronic applications. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.11.001

文献信息

• Novel luminescent phenothiazine-based Schiff bases with tuned morphology. Synthesis, structure, photophysical and thermotropic characterization
  作者：Andrei Zabulica、Mihaela Balan、Dalila Belei、Mitica Sava、Bogdan C. Simionescu、Luminita Marin

  DOI：10.1016/j.dyepig.2012.11.001

  日期：2013.3

  New Schiff base dimers based on phenothiazine heterocycle have been obtained with high yield and purity by condensation of 3-formyl-10-methyl-phenothiazine with various amines. The structural characterization was performed by elemental analysis, FTIR, 1D and 2D NMR spectroscopy and single crystal and powder wide angle X-ray diffraction. The obtained compounds have high thermal stability and some of them self-assemble into cubic mesophase and form stable molecular glass. The thermotropic study performed by polarized optical microscopy and differential scanning calorimetry revealed the possibility to control the compound morphology by thermal annealing and blending miscible components. The photophysical characterization indicates green light emission, with good absolute fluorescence quantum yield, large Stokes shift and high purity and fully saturated color. The special thermal behavior and photophysical properties appear to be significantly dependent on the special supramolecular architecture generated by the hockey-stick shape of the imino-phenothiazine mesogenic core.Collectively, the properties of these azomethines provide a starting point for new compounds with great advantages for optoelectronic applications. (C) 2012 Elsevier Ltd. All rights reserved.