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How Aromatic Are Molecular Nanorings? The Case of a Six-Porphyrin Nanoring**
- Source :
- Addi. Archivo Digital para la Docencia y la Investigación, instname, Angewandte Chemie (International Ed. in English), Digital.CSIC. Repositorio Institucional del CSIC
- Publication Year :
- 2021
- Publisher :
- Wiley, 2021.
-
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.<br />This work has been supported by grants from the Spanish government MICINN (PGC2018-098212-B-C21, PID2019-104772GB-I00, EUR2019-103825, PID2019-105488GB-I00, and PCI2019-103657), Diputación Foral de Gipuzkoa (2019-CIEN-000092-01), and Gobierno Vasco (IT1346-19, IT1254-19, PRE_2016_1_0159, and PIBA19-0004). E.R.C. acknowledges funding from the Juan de la Cierva program IJCI-2017-34658.
- Subjects :
- Materials science
NICS
Aromaticity | Hot Paper
electron delocalization
Conjugated system
Quantum chemistry
Catalysis
chemistry.chemical_compound
Delocalized electron
Molecule
nanoring
Research Articles
Aromaticity
General Chemistry
aromaticity
Porphyrin
Aromatic ring current
indexes
chemistry
Chemical physics
independent chemical-shifts
systems
delocalization error
Nanoring
ring
Research Article
conjugation
energy
Subjects
Details
- Database :
- OpenAIRE
- Journal :
- Addi. Archivo Digital para la Docencia y la Investigación, instname, Angewandte Chemie (International Ed. in English), Digital.CSIC. Repositorio Institucional del CSIC
- Accession number :
- edsair.doi.dedup.....98c73ab75276ba536a1051f782d9f32c