The sequential carbon-carbon bond cleaving reactions of the diketone derivative of C60 with o-phenylenediamine give a novel bowl-shaped fullerene bearing a 20-membered ring orifice. The product reversibly encapsulates a water molecule into the fullerene cage for the first time.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/ja038537a | DOI Listing |
Angew Chem Int Ed Engl
October 2024
Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi, 464-8603, Japan.
The synthesis of bowl-shaped antiaromatic molecules is challenging because the molecular distortion further destabilizes these already inherently reactive molecules. Here, we report the synthesis and properties of bowl-shaped fused anthrylnorcorroles that exhibit near-infrared (NIR) absorption reaching 1900 nm. The oxidation of meso-anthryldibromodipyrrin provides fused anthryldibromodipyrrin, which was converted to the fused mono- and bisanthrylnorcorroles through Ni(0)-mediated intramolecular coupling with a bis(dibromodipyrrin) Ni(II) complex.
View Article and Find Full Text PDFChemistry
January 2025
Research Center for Free Radical Chemistry, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Tianshui Southern Road 222, Lanzhou, 730000, Gansu Province, China.
Buckybowls, bowl-shaped polyaromatic hydrocarbons, have received intensive interest owing to their multifaceted potentials in supramolecular chemistry and materials science. Buckybowls possess unique chemical and physical properties associated with their concave and convex faces. In view of the shape complementarity, which is one of the key factors for host-guest assembly, buckybowls are ideal receptors for fullerenes.
View Article and Find Full Text PDFChem Sci
March 2024
Department of Materials Science, State Key Laboratory of Molecular Engineering of Polymers, Fudan University Shanghai 200433 China
π-Conjugated macrocycles have been highly attractive due to their challenging synthesis, fascinating aesthetic structure and unique physical and chemical properties. Although some progress has been made in synthesis, the study of π-macrocycles with different structural characteristics and supramolecular interactions still faces major challenges. In this paper, two new single-bond linked macrocycles (MS-4T/MS-6T) were reported, and the corresponding vinyl-bridged heterocycloarenes (MF-4T/MF-6T) were synthesized by the periphery fusion strategy.
View Article and Find Full Text PDFChem Commun (Camb)
February 2024
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116, China.
A bowl-shaped phosphangulene-protected cubic Cu nanocluster has been synthesized. The structure was determined by X-ray crystallography and further analyzed by multiple techniques. The phosphangulenes not only enable ligand substitutions with triphenylphosphines in a cluster-to-cluster transformation way, but also facilitate inter-cluster interactions with fullerenes.
View Article and Find Full Text PDFChemistry
December 2023
Department of Chemistry and Pharmacy, Friedrich-Alexander-Universität Erlangen-Nürnberg, Nikolaus-Fiebiger-Straße 10, 91058, Erlangen, Germany.
A novel buckybowl catcher with an extended π-surface has been synthesized via cross-coupling of two bowl shaped bromoindacenopicene moieties with a tolyl linker. The obtained catcher has been unambiguously characterized by 2D-NMR and mass spectrometry. DFT calculations indicate that the curved shape of the receptor moieties is favourable for binding fullerenes.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!