Date of Award
11-18-2015
Document Type
Thesis and Dissertation
Degree Name
Master of Science (MS)
Department
Department of Chemistry
First Advisor
Timothy D. Lash
Abstract
Carbaporphyrins have been the focus of many studies, and a wide variety of related carbaporphyrinoid systems have been reported. N-confused porphyrins are a class of carbaporphyrins where one pyrrole unit has been inverted. In this work, a newly discovered family of porphyrin isomers where one of the pyrrolic subunits is connected to the meso-bridges in a 1,3-fashion, called neo-confused porphyrins, has been investigated.
Reaction of pyrrole-3-carbaldehydes with acetoxymethylpyrroles and NaH in DMF gave neo-confused dipyrrylmethane dialdehydes. The resulting dialdehydes underwent an acid catalyzed condensation with a dipyrrylmethane to give neo-confused phlorins, and following oxidation with FeCl3 afforded new neo-confused porphyrins. These porphyrinoids differ from previous neo-confused porphyrins in that they do not possess fused benzo- units or electron withdrawing ester substituents. Instead, the neo-confused ring is substituted with a phenyl or bromo group. Reaction of neo-confused porphyrins with nickel(II) or palladium(II) acetate afforded the metaled complexes. The aromaticity of the neo-confused porphyrin and their derivatives were assured by proton NMR spectroscopy and UV-Vis spectroscopy.
Recommended Citation
Almejbel, Arwa Salem, "Synthesis And Characterization Of Neo-Confused Porphyrins And Related Systems" (2015). Theses and Dissertations. 486.
https://ir.library.illinoisstate.edu/etd/486
DOI
http://doi.org/10.30707/ETD2015.Almejbel.A
Page Count
144
Comments
Imported from ProQuest Almejbel_ilstu_0092N_10655.pdf