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How Aromatic Are Molecular Nanorings? The Case of a Six-Porphyrin Nanoring*.

ABSTRACT: Large conjugated rings with persistent currents are novel promising structures in molecular-scale electronics. A six-porphyrin nanoring structure that allegedly sustained an aromatic ring current involving 78π electrons was recently synthesized. We provide here compelling evidence that this molecule is not aromatic, contrary to what was inferred from the analysis of ¹ H-NMR data and computational calculations that suffer from large delocalization errors. The main reason behind the absence of an aromatic ring current in these nanorings is the low delocalization in the transition from the porphyrins to the bridging butadiyne linkers, which disrupts the overall conjugated circuit. These results highlight the importance of choosing a suitable computational method to study large conjugated molecules and the appropriate aromaticity descriptors to identify the part of the molecule responsible for the loss of aromaticity.

SUBMITTER: Casademont-Reig I

PROVIDER: S-EPMC8596448 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature

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How Aromatic Are Molecular Nanorings? The Case of a Six-Porphyrin Nanoring*.

Casademont-Reig Irene I Guerrero-Avilés Raúl R Ramos-Cordoba Eloy E Torrent-Sucarrat Miquel M Matito Eduard E

Angewandte Chemie (International ed. in English) 20210812 45

Large conjugated rings with persistent currents are novel promising structures in molecular-scale electronics. A six-porphyrin nanoring structure that allegedly sustained an aromatic ring current involving 78π electrons was recently synthesized. We provide here compelling evidence that this molecule is not aromatic, contrary to what was inferred from the analysis of <sup>1</sup> H-NMR data and computational calculations that suffer from large delocalization errors. The main reason behind the abs ...[more]

PMID: 34260804

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