Synthesis of polyionic tetraazaporphyrins and their Langmuir-Blodgett properties.

Date of Award


Publication Type

Master Thesis

Degree Name



Chemistry and Biochemistry


Chemistry, Physical.




Octaalkylthio tetraazaporphyrins (TAPS) having carboxylic acid moieties attached via alkyl spacers have been prepared as new polyionic discotics. Octaester TAP precursors were synthesized following the established Mg propanolate route and subsequently cleaved to the octaacid TAPs. Octaacid TAPs with spacers of 3, 5, and 10 methylene groups were studied by the Langmuir Blodgett technique at different pH values of the aq. subphase. Rigid Langmuir films of molecules with face-on orientation of the macrocycle were obtained, and could be transferred onto hydrophilic substrates by Z-deposition. Langmuir films were characterized by their isotherms, ellipsometry and Brewster angle microscopy whereas the transferred Langmuir Blodgett films were characterized by linear polarized UV/VIS spectroscopy or ellipsometry. The length of the aliphatic spacer and the pH of the subphase were found to be crucial in governing the interfacial properties of these octaacids. Octaazide TAPS were also prepared but their reduction to octaamines gave insoluble TAP products.Dept. of Chemistry and Biochemistry. Paper copy at Leddy Library: Theses & Major Papers - Basement, West Bldg. / Call Number: Thesis2006 .D846. Source: Masters Abstracts International, Volume: 45-01, page: 0328. Thesis (M.Sc.)--University of Windsor (Canada), 2006.

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