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Global Aromaticity and Antiaromaticity in Porphyrin Nanoring Anions

preprint
submitted on 27.07.2019 and posted on 29.07.2019 by Martin D. Peeks, Michael Jirasek, Timothy D. W. Claridge, Harry L. Anderson
Doping, through oxidation or reduction, is often used to modify the properties of π-conjugated oligomers. In most cases, the resulting charge distribution is difficult to determine. If the oligomer is cyclic and doping establishes global aromaticity or antiaromaticity, then it is certain that the charge is fully delocalized over the entire perimeter of the ring. Here we show that reduction of a six-porphyrin nanoring using decamethylcobaltocene results in global aromaticity (in the 6– state; [90 π]) and antiaromaticity (in the 4– state; [88 π]), consistent with Hückel’s rules. Aromaticity is assigned by NMR spectroscopy and density-functional theory calculations.

Funding

Supramolecular Nanorings for Exploring Quantum Interference

Engineering and Physical Sciences Research Council

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Porphyrin Nanorings

Engineering and Physical Sciences Research Council

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Quantum Effects in Electronic Nanodevices (QuEEN)

Engineering and Physical Sciences Research Council

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Cooperative Phenomena in Supramolecular Nanostructures

European Research Council

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History

Email Address of Submitting Author

m.peeks@unsw.edu.au

Institution

University of New South Wales

Country

Australia

ORCID For Submitting Author

0000-0002-9057-9444

Declaration of Conflict of Interest

no conflict of interest

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in Angewandte Chemie International Edition

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