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

  • Irene Casademont-Reig
  • , Raúl Guerrero-Avilés
  • , Eloy Ramos-Cordoba*
  • , Miquel Torrent-Sucarrat*
  • , Eduard Matito*
  • *Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

54 Citations (Scopus)

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 1H-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.

Original languageEnglish
Pages (from-to)24080-24088
Number of pages9
JournalAngewandte Chemie - International Edition
Volume60
Issue number45
DOIs
Publication statusPublished - 2 Nov 2021
Externally publishedYes

Keywords

  • aromaticity
  • delocalization error
  • nanoring

Fingerprint

Dive into the research topics of 'How Aromatic Are Molecular Nanorings? The Case of a Six-Porphyrin Nanoring**'. Together they form a unique fingerprint.

Cite this