An Indacenopicene‐based Buckybowl Catcher for Recognition of Fullerenes

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...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry : a European journal 2023-12, Vol.29 (70), p.e202302778-n/a
Main Authors: Scholz, Barbara, Oshchepkov, Alexander S., Papaianina, Olena, Ruppenstein, Cordula, Akhmetov, Vladimir A., Sharapa, Dmitry I., Amsharov, Konstantin Y., Pérez‐Ojeda, M. Eugenia
Format: Article
Language:English
Subjects:
Aromaticity
Binding
Buckminsterfullerene
buckycatcher
Calorimetry
Chemistry
Cross coupling
Fullerenes
host-guest systems
indacenopicene
Magnetic resonance spectroscopy
Mass spectrometry
Mass spectroscopy
NMR
NMR spectroscopy
Nuclear magnetic resonance
supramolecular chemistry
Titration
Titration calorimetry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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 C60 and C70 utilizing NMR spectroscopy and isothermal titration calorimetry (ITC). The resulting binding values show a higher affinity of the catcher towards C70 over C60. The designed catcher demonstrated the fundamental possibility of creating sensors for spherical aromaticity. A novel type of buckycatcher based on two bowl‐shaped bromoindacenopicene moieties was synthesized and characterized by NMR and mass spectrometry. DFT calculations show a shape fit of the catcher cavity for fullerene binding. Interactions were confirmed for C60 and C70 utilizing NMR spectroscopy and isothermal titration calorimetry (ITC).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202302778