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Issue 27, 2012
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The origin of global and macrocyclic aromaticity in porphyrinoids

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Abstract

The global and macrocyclic aromaticity of porphyrinoids was characterized using our graph theory of aromaticity. The sequential line plots of topological resonance energy (TRE) against the number of π-electrons (Nπ) for different porphyrinoids are similar with four major extrema to those for five-membered heterocycles. This supports the view that five-membered rings are the main origin of global aromaticity in porphyrinoids. Macrocyclic circuits contribute significantly to macrocyclic π-circulation but modestly to global aromaticity. Macrocyclic aromaticity/antiaromaticity in oligopyrrolic macrocycles can be predicted by formally applying Hückel's [4n + 2] rule to an annulene-like main macrocyclic conjugation pathway (MMCP). This bridged annulene model can be justified by examining the contribution of individual macrocyclic circuits to macrocyclic aromaticity. A Hückel-like rule of macrocyclic aromaticity was found for porphyrinoid species.

Graphical abstract: The origin of global and macrocyclic aromaticity in porphyrinoids

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Publication details

The article was received on 07 Dec 2011, accepted on 15 May 2012 and first published on 16 May 2012


Article type: Paper
DOI: 10.1039/C2OB25692D
Citation: Org. Biomol. Chem., 2012,10, 5219-5229
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    The origin of global and macrocyclic aromaticity in porphyrinoids

    Y. Nakagami, R. Sekine and J. Aihara, Org. Biomol. Chem., 2012, 10, 5219
    DOI: 10.1039/C2OB25692D

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