Graduation Term
Summer 2025
Degree Name
Master of Science (MS)
Department
Department of Chemistry
Committee Chair
Timothy D Lash
Committee Member
Shawn R. Hitchcock
Committee Member
Susil Baral
Abstract
Porphyrinoid systems constitute a widely studied class of cyclic tetrapyrrole macrocycles. While naturally prevalent in crucial biological processes as metalloporphyrins, such as heme and chlorophyll, these structures also exhibit intriguing spectroscopic properties commonly attributed to their [18]annulene-like delocalization pathway, contributing to their inherent aromaticity. Research in this area frequently involves modifications of subunits.
This study investigates phenaliporphyrin, a novel porphyrinoid system, conceived to overcome the inherent nonaromatic character observed in benziporphyrins. The nonaromaticity of benziporphyrins arises from the strong resonance stabilization of their benzene subunit, which actively counteracts the development of a global porphyrinoid aromatic system. By incorporating a phenalene unit, our design aimed to restore aromaticity in phenaliporphyrin by facilitating a continuous 18π-electron conjugation pathway.
Furthermore, this work explores the synthesis of carbachlorins, which are synthetic analogues of chlorin where core nitrogen atoms are replaced by carbon. Our investigation into carbachlorins aims to address the relative paucity of comprehensive research into these compelling macrocyclic systems.
Access Type
Thesis-Open Access
Recommended Citation
Jacob, Sunday O., "Development of a Novel Route to Phenaliporphyrin and Investigations into the Synthesis of Carbachlorins" (2025). Theses and Dissertations. 2157.
https://ir.library.illinoisstate.edu/etd/2157
DOI
https://doi.org/10.30707/ETD.1763755358.987944
Included in
Heterocyclic Compounds Commons, Organic Chemicals Commons, Pharmaceutical Preparations Commons