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Journal of the American Chemical Society

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American Chemical Society





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The synthesis and characterization of a new phthalocyanine(Pc) Mn-nitride complex, (OEtPc)MnN (2; OEtPc= 1,4,8,11,15,18,22,25-octaethoxy-Pc), as well as its stable, readily accessible oxidized (2+ and 22+) and reduced (2-, 22-) congeners is reported. This unique isostructural series displays switchable aromatic character spanning the aromatic (2), non-aromatic (22+), and antiaromatic (22-) triad, in addition to the open-shell radical states (2+, 2-). All complexes were structurally characterized and displayed significant structural distortions at the redox extrema (22+, 22-) consistent with proposed [16 or 18]annulene π ring circuit models. Spectroscopic and computational studies further support these models. This isolated, fully characterized, isostructural series spanning five redox states (22+, 2+, 2, 2-, 22-) is unique in both the Pc and related macrocyclic (ex. porphyrinoids) literature and may offer direct insight into structural-electronic correlations driven by switchable aromaticity.


This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see

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