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The Synthesis and Characterization of Imidazolium Lithium Phthalocyanines

Kelley, John J.
http://rave.ohiolink.edu/etdc/view?acc_num=wright1221535816

Abstract Details

2008, Master of Science (MS), Wright State University, Chemistry.
A series of 1,3-di-substituted-imidazolium lithium phthalocyanines, in which the substituents on the imidazolium nitrogens were combinations of methyl, ethyl, pentyl, hexyl, isopropyl, adamantyl or 2,4,6-trimethylphenyl groups, was synthesized. The cation exchange of a single lithium ion of dilithium phthalocyanine for a 1,3-disubstituted-imidazolium ion was performed by mixing their salts in common organic solvents under ambient conditions. This afforded a number of imidazolium lithium phthalocyanines in moderate yields. They exhibited poor solubility in most solvents. Their composition and purity were initially verified by 1H and 13C-NMR and elemental analysis. The 1H-NMR spectra also indicated that the imidazolium and lithium phthalocyanine ions are present in a 1:1 ratio. Infrared spectra confirmed the C-C and C-N stretching modes that are characteristic of phthalocyanine and imidazolium aromatic structures. UV-Vis spectra for each compound showed essentially no change in absorption from that of dilithium phthalocyanine, which suggests a lack of influence of the imidazolium ions. Thermal properties of the title compounds were determined through melting points and TGA, in which high melting temperatures (330-370°C) were seen for several complexes and lowered thermal stability was seen for all. The crystal structure of the bis(adamantyl)imidazolium derivative was determined through X-ray diffraction. It was found that water molecules are associated to imidazolium and lithium phthalocyanine ions through hydrogen-bonding, which is possibly the basis for crystallization in imidazolium-lithium-phthalocyanines.
William Feld, PhD (Advisor)
David Grossie, PhD (Committee Member)
David Dolson, PhD (Committee Member)
Kenneth Turnbull, PhD (Other)
Joseph F. Thomas, Jr., PhD (Other)
136 p.
Chemistry
dilithium phthalocyanine; imidazolium; phthalocyanine; NMR; FT-IR; TGA; UV-Vis; Single Crystal X-ray Diffraction

Recommended Citations

Citations

  • Kelley, J. J. (2008). The Synthesis and Characterization of Imidazolium Lithium Phthalocyanines [Master's thesis, Wright State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=wright1221535816

    APA Style (7th edition)

  • Kelley, John. The Synthesis and Characterization of Imidazolium Lithium Phthalocyanines. 2008. Wright State University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=wright1221535816.

    MLA Style (8th edition)

  • Kelley, John. "The Synthesis and Characterization of Imidazolium Lithium Phthalocyanines." Master's thesis, Wright State University, 2008. http://rave.ohiolink.edu/etdc/view?acc_num=wright1221535816

    Chicago Manual of Style (17th edition)

wright1221535816
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© 2008, all rights reserved.
This open access ETD is published by Wright State University and OhioLINK.