Synthesis of
Porphyrin-Imidazolium-Ferrocene Complexes as Precursors to
Porphyrin Arrays
Alison Hyslop, Department of
Chemistry, St. John’s College of Liberal Arts and Sciences
Samantha Blondel, Jennifer Chabra, Weici
Fang, Maung–Tin Htoo Kway, and Elissa Ramcharitar, St.
John's University Student
Abstract: Porphyrin arrays are
ubiquitous in nature and play a key role in light harvesting
processes in photosynthesis through absorbing light energy and
transferring the energy to a reaction center. Porphyrins and
metalloporphyrins compounds are used in energy conversion and in
molecular-scale electronic devises. The synthesis of
asymmetric porphyrin derivatives is of great interest for the
development of new molecular structures. Our research
interests lie in the formation of porphyrin arrays through novel
binding modes to metal centers. We are interested in the
synthesis of porphyrin arrays utilizing imidazole and pyridyl rings
to link porphyrins to metal centers. The first project is the
synthesis of porphyrin–imidazole compounds, and the imidazole ring
affords two binding sites, the unsubstituted nitrogen can act as a
Lewis base to coordinate to a metal or by substituting both
nitrogens, the N-heterocyclic carbene can be formed and this
carbene used to bind to metals. The second project, in
collaboration with Dr. Elise Megehee, is the formation of a series
of porphyrin–pyridyl–osmium compounds with a variety of
substituents on the osmium metal center which will modulate the
electronics of the system and will affect the energy transfer and
electron transfer properties of the system.