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Porphine or porphin is an organic compound of empirical formula C20H14N4. It is heterocyclic and aromatic. The molecule is a flat macrocycle, consisting of four pyrrole-like rings joined by four methine bridges, which makes it the simplest of the tetrapyrroles.
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Phosphorus-centered porphyrins are conjugated polycyclic ring systems consisting of either four pyrroles with inward-facing nitrogens and a phosphorus atom at their core or porphyrins with one of the four pyrroles substituted for a phosphole. Unmodified porphyrins are composed of pyrroles and linked by unsaturated hydrocarbon bridges often acting as multidentate ligands centered around a transition metal like Cu II, Zn II, Co II, Fe III. Being highly conjugated molecules with many accessible energy levels, porphyrins are used in biological systems to perform light-energy conversion and modified synthetically to perform similar functions as a photoswitch or catalytic electron carriers. Phosphorus III and V ions are much smaller than the typical metal centers and bestow distinct photochemical properties unto the porphyrin. Similar compounds with other pnictogen cores or different polycyclic rings coordinated to phosphorus result in other changes to the porphyrin’s chemistry.
References
- 1 2 3 4 5 6 "Dr. Timothy Lash "Distinguished Professor, Organic Chemistry"". chemistry.illinoisstate.edu. illinoisstate.edu.
- 1 2 3 Lash, Timothy D. (November 2007). "Recent Advances on the Synthesis and Chemistry of Carbaporphyrins and Related Porphyrinoid Systems". European Journal of Organic Chemistry. 2007 (33): 5461–5481. doi:10.1002/ejoc.200700478.
- ↑ Kadish, Karl M.; Smith, Kevin M.; Guilard, Roger (2016). Handbook of Porphyrin Science – With Applications to Chemistry, Physics, Material Science, Engineering, Biology and Medicine (Volume 16) "Chapter 74 – Carbaporphyrins and Related Systems. Synthesis, Characterization, Reactivity and Insights into the Nature of Porphyrinoid Aromaticity". Vol. 40. World Scientific Publishing. doi:10.1142/10055. ISBN 978-9814417280.
