Date of Award
11-18-2015
Document Type
Thesis
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