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Synthesis and characterization of octa-alkyl-substituted metallophthalocyanines and noncentrosymmetrical metallophthalocyanines.

机译：八烷基取代的金属酞菁和非中心对称的金属酞菁的合成与表征。

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摘要

Octylthio and octylsulfonyl metallophthalocyanines (MPcs) [M: Ni, Cu, Co, and Zn] were synthesized and characterized by spectroscopic, magnetic, and electrochemical measurements. The overall B and Q bands of octylsufonyl MPcs are blue-shifted, compared to octylthio MPcs due to electron attracting octylsulfonyl groups in the UV-Vis spectrum. In each series of octylthio and octylsulfonyl MPcs, the B (Soret) and Q band of NiPc are more blue-shifted than the other MPcs due to stronger electronegativity of the nickel central metal ion. Octylthio ZnPc gives the highest intensity of emission spectrum.; Octylthio NiPc and CoPc crystals are fibrous needles which are unsuitable for X-ray single crystal diffraction.; The broad EPR signal was observed in CuPc and CoPc because of the paramagnetic properties of central metal ions. The g value of octylthio CoPc increases with decreasing temperature due to more efficient spin-orbital coupling of the unpaired electron at lower temperature.; The redox potentials of MPcs were investigated by using cyclic voltammetry. All samples show quasi-reversible or irreversible voltammograms. Consequently, Δredox of octylsulfonyl MPcs does not present consistent increase, as expected, compared to Δredox of octylthio MPcs in contrast to the blue shift of the Q band in most octylsulfonyl MPcs, compared to octylthio MPcs in UV Vis spectrum.; In the second part of the thesis, we prepared a non-centrosymmetrical NiPc containing one triazole subunit and its complex with silver ions. The B (Soret) and Q band of silver dimer complex were blue-shifted against NiPc due to the electron-withdrawing effect of silver metal ions in the UV-Vis spectrum. FT IR spectroscopy was rather insensitive to NO3 − counter ions. Atomic Absorption Spectroscopy (AAS) showed a 10% of silver content in the sample solution. This is in fair agreement with a 7% silver content in the dimer complex.; In the third part of the thesis, we prepared a non-centrosymmetrical ZnPc containing one phenanthroline subunit. The B (Soret) band is seen around 360 nm and is red-shifted, compared to other metallophthalocyanines due to the extended π systems.
机译：合成了辛基硫基和辛基磺酰基金属酞菁（Mcs：Ni，Cu，Co和Zn），并通过光谱，磁和电化学测量对其进行了表征。与辛硫基MPcs相比，由于硫在UV-Vis光谱中吸引了辛基磺酰基，因此辛基磺酰基MPcs的整个B和Q带发生了蓝移。在每个系列的辛硫基和辛基磺酰基MPcs中，由于镍中心金属离子的电负性较强，NiPc的B（Soret）和Q带比其他MPcs蓝移更多。辛硫基ZnPc具有最高的发射光谱强度。辛硫基NiPc和CoPc晶体是不适合X射线单晶衍射的纤维针。由于中心金属离子的顺磁特性，在CuPc和CoPc中观察到了宽的EPR信号。辛硫基CoPc的g值随温度降低而增加，这是由于未配对电子在较低温度下更有效的自旋轨道耦合。使用循环伏安法研究了MPcs的氧化还原电位。所有样品均显示准可逆或不可逆伏安图。因此，与预期的辛基磺酰基MPcs的Δredox相比，与辛硫基MPcs的Δredox相比，并没有表现出一致的增加，而与大多数辛基磺酰基MPcs的Q谱带的蓝移相比，与UV Vis光谱中的辛硫基MPcs相比。在论文的第二部分，我们制备了一种非中心对称的NiPc，它含有一个三唑亚基及其与银离子的络合物。由于在紫外-可见光谱中银金属离子的电子吸收作用，银二聚体配合物的B（Soret）和Q带相对NiPc发生了蓝移。 FT IR光谱对NO3 -抗衡离子非常不敏感。原子吸收光谱法（AAS）显示样品溶液中银的含量为10％。这与二聚体中银含量为7％完全吻合。在论文的第三部分，我们制备了包含一个菲咯啉亚基的非中心对称ZnPc。与其他金属酞菁类化合物相比，由于扩展的π系统，B（Soret）带可见于360 nm附近，并发生了红移。

著录项

  • 作者

    Chang, Seung Wook.;

  • 作者单位

    Polytechnic University.;

  • 授予单位 Polytechnic University.;
  • 学科 Chemistry Organic.
  • 学位 Ph.D.
  • 年度 2003
  • 页码 101 p.
  • 总页数 101
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 有机化学;
  • 关键词

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