An Indacenopicene-based Buckybowl Catcher for Recognition of Fullerenes

A novel buckybowl catcher with an extended pi-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).image

Automated summary

A novel buckybowl catcher with an extended pi-surface was synthesized and characterized. The effective binding of the catcher with C60 and C70 was confirmed, with higher affinity towards C70. This study demonstrates the potential of creating sensors for spherical aromaticity.