An Indacenopicene-based Buckybowl Catcher for Recognition of Fullerenes.

Autor: Scholz B; Department of Chemistry and Pharmacy, Friedrich-Alexander-Universität Erlangen-Nürnberg, Nikolaus-Fiebiger-Straße 10, 91058, Erlangen, Germany., Oshchepkov AS; Department of Physics, Max Planck Institute for the Science of Light, 91058, Erlangen, Germany., Papaianina O; Department of Chemistry and Pharmacy, Friedrich-Alexander-Universität Erlangen-Nürnberg, Nikolaus-Fiebiger-Straße 10, 91058, Erlangen, Germany., Ruppenstein C; Institute of Chemistry, Organic Chemistry, Martin-Luther-University Halle-Wittenberg, 06120, Halle (Saale), Germany., Akhmetov VA; Institute of Chemistry, Organic Chemistry, Martin-Luther-University Halle-Wittenberg, 06120, Halle (Saale), Germany., Sharapa DI; Institute of Catalysis Research and Technology, Karlsruhe Institute of Technology, Hermann-von-Helmholtz-Platz 1, 76344, Eggenstein-Leopoldshafen, Germany., Amsharov KY; Institute of Chemistry, Organic Chemistry, Martin-Luther-University Halle-Wittenberg, 06120, Halle (Saale), Germany., Pérez-Ojeda ME; Department of Chemistry and Pharmacy, Friedrich-Alexander-Universität Erlangen-Nürnberg, Nikolaus-Fiebiger-Straße 10, 91058, Erlangen, Germany.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2023 Dec 14; Vol. 29 (70), pp. e202302778. Date of Electronic Publication: 2023 Oct 24.
DOI: 10.1002/chem.202302778
Abstrakt: 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. Effective binding was confirmed for interactions with C 60 and C 70 utilizing NMR spectroscopy and isothermal titration calorimetry (ITC). The resulting binding values show a higher affinity of the catcher towards C 70 over C 60 . The designed catcher demonstrated the fundamental possibility of creating sensors for spherical aromaticity.
(© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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