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Izomery porfiryny : podobieństwa i różnice

Waluk Jacek

Wiadomości Chemiczne

2021

[Z] 75, 5-6

631--652

Porphyrins, “pigments of life”, are extremely popular objects of fundamental research and as candidates for diverse applications. The prerequisite for a successful application is the understanding of the electronic structure. For that purpose, it is instructive to compare the properties of porphyrin with those of its isomers. To date, six such isomers have been synthesized. In this work, we compare the characteristics of all “nitrogen-in”, N-confused- and neo-confused porphyrin isomers, including three structures that have not yet been obtained. We discuss the electronic spectra, intramolecular hydrogen bonding, and tautomerism. Analysis of the energy pattern of frontier orbitals allows predicting the redox properties, as well as the pattern of electronic absorption and magnetic circular dichroism (MCD) spectra. In turn, the geometry of the inner cavity is the factor that determines the strength of hydrogen bonds and, in consequence, the kinetics of tautomerization.