Circumcoronene, a hexagonal graphene fragment with six zigzag edges, has been the focus of theoretical studies for many years, but its synthesis in solution has remained a challenge. In this study, we present a facile method for synthesizing three derivatives of circumcoronene using Brønsted/Lewis acid-mediated cyclization of vinyl ether or alkyne. Their structures were confirmed through X-ray crystallographic analysis. Bond length analysis, NMR measurement, and theoretical calculations showed that circumcoronene mostly follows Clar's bonding model and exhibits dominant local aromaticity. Its absorption and emission spectra are similar to those of the smaller hexagonal coronene due to its six-fold symmetry.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/anie.202301041 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
A Crowning Achievement: The First Solution-Phase Synthesis of Circumcoronenes.
Angew Chem Int Ed Engl
July 2023
Department of Chemistry and Applied Biosciences, ETH Zürich, Vladimir-Prelog-Weg 2, 8093, Zürich, Switzerland.
Circumcoronene is a highly symmetric polybenzenoid hydrocarbon that has fascinated organic chemists and materials scientists for decades. However, until recently, it had only been studied theoretically, because its synthesis in solution remained challenging. In a recent report, Wu and co-workers described the first successful solution-phase synthesis and isolation of crystalline circumcoronene derivatives, validating the long-predicted Clar structure.
View Article and Find Full Text PDFCircumcoronenes.
Angew Chem Int Ed Engl
May 2023
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543, Singapore.
Circumcoronene, a hexagonal graphene fragment with six zigzag edges, has been the focus of theoretical studies for many years, but its synthesis in solution has remained a challenge. In this study, we present a facile method for synthesizing three derivatives of circumcoronene using Brønsted/Lewis acid-mediated cyclization of vinyl ether or alkyne. Their structures were confirmed through X-ray crystallographic analysis.
View Article and Find Full Text PDFUltrahigh-yield on-surface synthesis and assembly of circumcoronene into a chiral electronic Kagome-honeycomb lattice.
Sci Adv
January 2021
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore.
On-surface synthesis has revealed remarkable potential in the fabrication of atomically precise nanographenes. However, surface-assisted synthesis often involves multiple-step cascade reactions with competing pathways, leading to a limited yield of target nanographene products. Here, we devise a strategy for the ultrahigh-yield synthesis of circumcoronene molecules on Cu(111) via surface-assisted intramolecular dehydrogenation of the rationally designed precursor, followed by methyl radical-radical coupling and aromatization.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!