Date of Completion
Porphyrin, Chlorin, Bacteriochlorin, Expanded Bacteriochlorins, Porphyrinoids, Pyrrole-Modified Porphyrins, Aromatic Macrocycles, Heterocycles, Synthetic Methods, Spectroscopic Methods
Prof. Christian Brückner
Prof. Amy R. Howell
Prof. Mark W. Peczuh
Prof. Alfredo Angeles-Boza
Field of Study
Doctor of Philosophy
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.
Samankumara, Lalith P., "Bacteriochlorins and Bacteriochlorin Analogs from meso-Tetraarylporphyrins" (2013). Doctoral Dissertations. 216.