期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 45, 页码 24080-24088出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202108997
关键词
aromaticity; delocalization error; nanoring
资金
- Spanish government MICINN [PGC2018-098212-B-C21, PID2019-104772GB-I00, EUR2019-103825, PID2019-105488GB-I00, PCI2019-103657]
- Diputacion Foral de Gipuzkoa [2019-CIEN-000092-01]
- Gobierno Vasco [IT1346-19, IT1254-19, PRE_2016_1_0159, PIBA19-0004]
- Juan de la Cierva program [IJCI-2017-34658]
This study reveals the relationship between electronic properties and aromaticity in ring structures, indicating the reasons for the lack of aromaticity in the six-porphyrin nanoring structure and further emphasizing the importance of choosing appropriate computational methods and descriptors.
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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