ArticleChemistry (Weinheim an der Bergstrasse, Germany)2023
Quest for the Most Aromatic Pathway in Charged Expanded Porphyrins.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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7 citing papers in PubMed, 21 citations in OpenAlex.
- Theoretical study on the geometry, aromaticity and electronic properties of porphyrin analogues.RSC advances · 2026Article
- Hydride Transfer Limits Hydrogen Evolution Efficiency With Zn Porphyrin Photocatalysts.Chemistry, an Asian journal · 2026Article
- Unlocking red-to-near-infrared luminescence via ion-pair assembly in carbodicarbene borenium ions.Nature chemistry · 2026Article
- From (Sub)Porphyrins to (Sub)Phthalocyanines: Aromaticity Signatures in the UV-Vis Absorption Spectra.Inorganic chemistry · 2024Article
- Application of Inverse Design Approaches to the Discovery of Nonlinear Optical Switches.Molecules (Basel, Switzerland) · 2023Article
- Assessment of the performance of six indices in predicating the aromaticity of planar porphyrinoids.Journal of molecular modeling · 2023Article
- Quest for the Most Aromatic Pathway in Charged Expanded Porphyrins.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
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Authors and funding
8 authors at 4 institutions in 5 countries.
Funding
Abstract
Despite 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 AV
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