Date of Completion

8-22-2013

Embargo Period

8-22-2013

Keywords

Porphyrin, Chlorin, Bacteriochlorin, Expanded Bacteriochlorins, Porphyrinoids, Pyrrole-Modified Porphyrins, Aromatic Macrocycles, Heterocycles, Synthetic Methods, Spectroscopic Methods

Major Advisor

Prof. Christian Brückner

Associate Advisor

Prof. Amy R. Howell

Associate Advisor

Prof. Mark W. Peczuh

Associate Advisor

Prof. Alfredo Angeles-Boza

Field of Study

Chemistry

Degree

Doctor of Philosophy

Open Access

Open Access

Abstract

This dissertation focuses on the development of new synthetic methodologies for the preparation of meso-tetraaryl­bacterio­chlorin analogs in which one or two opposite pyrrollic moieties were formally replaced by non-pyrrolic groups, such as morpholine, indanone, oxazolone. In particular, starting form the osmylation of porpyrins, to generate bacteriochlorin tetraols, the first syntheses of ring-expanded and ring-cleaved bacteriochlorin derivatives are discussed. Solid-state structures of most of these compounds were determined, and the underlined structure photo­physical property relationships were studied.

This dissertation introduces a number of novel bacteriochlorin chromophores with singnificantly red-shifted UV-visible spectra compared to their starting porphyrinoids. Thus, their facile availability, relative chemical stability and optical properties suggest their uses in artificial light-harvesting and biomedical applications.

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