3,7-bis(ferrocenylethynyl)-10-methylphenothiazine | 928768-55-2

• 英文名称: 3,7-bis(ferrocenylethynyl)-10-methylphenothiazine
• CAS: 928768-55-2
• 化学式: C₃₇H₂₇Fe₂NS
• 分子量: 629.388
• InChiKey: WYVFRSSJQYIQJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为产物：
  描述：

  二茂铁乙炔 、 3,7-dibromo-10-methyl-10H-phenothiazine 在 bis(triphenylphosphine)palladium(II) dichloride 、 copper(I) iodide 、 triethylamine 作用下， 以 三乙胺 为溶剂， 以42.1%的产率得到3,7-bis(ferrocenylethynyl)-10-methylphenothiazine
  参考文献：
  名称：

  Ferrocene−Phenothiazine Conjugated Molecules:  Synthesis, Structural Characterization, Electronic Properties, and DFT-TDDFT Computational Study

  摘要：

  Two novel Fc-MPT conjugated compounds, 3-(ferrocenylethynyl)-10-methylphenothiazine (1) and 3,7-bis(ferrocenylethynyl)-10-methylphenothiazine (2), have been synthesized by Sonogashira cross-coupling reactions. Single-crystal X-ray diffraction shows that 2 displays better coplanarity between the Fc and MPT subunits. The crystal packing reveals that 1 stacks in the same direction between the neighboring molecules by the S center dot center dot center dot H-C (of the Fc moiety) hydrogen bonds, while 2 stacks in an inverse fashion between the adjacent molecules, not only by the S center dot center dot center dot H-C (of the MPT moiety) hydrogen bonds but also by pi center dot center dot center dot pi interactions. Both complexes show MLCT, ICT, and pi -> pi* transitions in the UV-visible range in solution, and 2 has a tremendous bathochromic shift and shows a higher oscillator strength of the absorption, which has been verified by TDDFT theoretical calculations. DFT calculations explain the electrochemistry of the two complexes and show that the larger conjugative effect in 2 leads to the smaller HOMO-LUMO gap (E-g). The differences between 1 and 2 indicate that the structural and conjugative effects have great influence on the electronic properties of the molecules.

  DOI：

  10.1021/om060923o