Local versus global aromaticity in azuliporphyrin and benziporphyrin derivatives

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Authors

GHOSH A. LARSEN S. CONRADIE J. FOROUTANNEJAD Cina

Year of publication 2018
Type Article in Periodical
Magazine / Source ORGANIC & BIOMOLECULAR CHEMISTRY
MU Faculty or unit

Central European Institute of Technology

Citation
Doi http://dx.doi.org/10.1039/c8ob01672k
Keywords ORGANOMETALLIC CHEMISTRY; PORPHYRINOID AROMATICITY; MOLECULAR-STRUCTURES; CURRENT DENSITIES; CARBAPORPHYRINS; PATHWAYS; NICKEL(II); INSIGHTS; ELECTROCHEMISTRY; CARBACHLORINS
Description Carbaporphyrinoids afford fascinating examples of competition between local and global aromaticity in conjugated, polycyclic systems. Thus, whereas density functional theory calculations reveal only a modest effect of metal complexation on the current density profiles of true carbaporphyrins and azuliporphyrins, the impact is much greater for benziporphyrins, underscoring a strong competition between local and global aromaticity in the latter system. Furthermore, the calculations shed light on the remarkable efficacy of suitably placed electron-donating substituents on the benzene ring in boosting the global diatropic currents in a metallobenziporphyrin.
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