This dissertation concerns the description of porphyrin analogs in which one pyrrolic moiety was replaced by non-pyrrolic heterocycle. Their general structures of the resulting pyrrole-modified porphyrins (PMPs) are represented by structures A or B. Focus is on the description of their syntheses and chemical transformations. In particular, the synthesis of porpholactones, chlorolactones, porpholactams, chlorolactams, imidazoloporphyrins, and morpholinochlorins are discussed. The crystal structures of many porphyrinoids prepared and the determination of the underlying structure-optical properties relationships are described.*.;In due course of the work toward PMPs, an efficient pathway toward quinoline-annulated porphyrins was discovered. The syntheses, structures, and spectroscopic properties of this class of peripherally modified porphyrins are also discussed.;Thus, this dissertation introduces a number of novel porphyrin-based chromophore classes with significantly red-shifted optical spectra compared to the parent porphyrins. The facile access to many of the compound classes, their optical properties, and their chemical stability suggest their uses in light harvesting and biomedical applications.;*Please refer to dissertation for diagrams.
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