Quest for the Most Aromatic Pathway in Charged Expanded Porphyrins

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dc.contributor.authorCasademont-Reig, Irene
dc.contributor.authorWoller, Tatiana
dc.contributor.authorGarcía, Victor
dc.contributor.authorContreras-García, Julia
dc.contributor.authorTiznado, William
dc.contributor.authorTorrent-Sucarrat, Miquel
dc.contributor.authorMatito, Eduard
dc.contributor.authorAlonso, Mercedes
dc.date.accessioned2024-09-04T20:31:28Z
dc.date.available2024-09-04T20:31:28Z
dc.date.issued2023-01
dc.descriptionIndexación: Scopus
dc.description.abstractDespite the central role of aromaticity in the chemistry of expanded porphyrins, the evaluation of aromaticity remains difficult for these extended macrocycles. The presence of multiple conjugation pathways and different planar and nonplanar π-conjugation topologies makes the quantification of global and local aromaticity even more challenging. In neutral expanded porphyrins, the predominance of the aromatic conjugation pathway passing through the imine-type nitrogens and circumventing the amino NH groups is established. However, for charged macrocycles, the question about the main conjugation circuit remains open. Accordingly, different conjugation pathways in a set of neutral, anionic, and cationic expanded porphyrins were investigated by means of several aromaticity indices rooted in the structural, magnetic, and electronic criteria. Overall, our results reveal the predominance of the conjugation pathway that passes through all nitrogen atoms to describe the aromaticity of deprotonated expanded porphyrins, while the outer pathway through the perimeter carbon atoms becomes the most aromatic in protonated macrocycles. In nonplanar and charged macrocycles, a discrepancy between electronic and magnetic descriptors is observed. Nevertheless, our work demonstrates AVmin remains the best tool to determine the main conjugation pathway of expanded porphyrins. © 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
dc.description.urihttps://chemistry-europe-onlinelibrary-wiley-com.recursosbiblioteca.unab.cl/doi/10.1002/chem.202202264
dc.identifier.citationChemistry - A European Journal. Volume 29, Issue 6. 27 January 2023. Article number e202202264
dc.identifier.doi10.1002/chem.202202264
dc.identifier.issn0947-6539
dc.identifier.urihttps://repositorio.unab.cl/handle/ria/59806
dc.language.isoen
dc.publisherJohn Wiley and Sons Inc
dc.rights.licenseCC BY-NC-ND 4.0 Attribution-NonCommercial-NoDerivatives 4.0 International Deed
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/4.0/
dc.subjectAnnulene Model
dc.subjectAromaticity
dc.subjectCharged Macrocycles
dc.subjectPorphyrinoids
dc.subjectRing Currents
dc.titleQuest for the Most Aromatic Pathway in Charged Expanded Porphyrins
dc.typeArtículo
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