How Aromatic Are Molecular Nanorings? The Case of a Six-Porphyrin Nanoring**
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 78 pi electrons was recently synthesized. We provide here compelling evidence that this molecu...
| Authors: | , , , , |
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| Format: | article |
| Publication Date: | 2021 |
| Country: | España |
| Institution: | Universidad del País Vasco |
| Repository: | Addi. Archivo Digital para la Docencia y la Investigación |
| OAI Identifier: | oai:addi.ehu.eus:10810/53660 |
| Online Access: | http://hdl.handle.net/10810/53660 |
| Access Level: | Open access |
| Keyword: | aromaticity delocalization error nanoring independent chemical-shifts electron delocalization ring conjugation indexes systems energy NICS |
| Summary: | 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 78 pi electrons was recently synthesized. We provide here compelling evidence that this molecule is not aromatic, contrary to what was inferred from the analysis of H-1-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. |
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