A Double Concave Hydrocarbon Buckycatcher

Abstract

Double Diels−Alder addition of isocorannulenofuran to dibenzocyclooctadiyne followed by deoxygenation produces a molecular tweezers C60H28 with two corannulene pincers and a tetrabenzocyclooctatetraene tether. X-ray crystal structure determination of its inclusion complex with buckminsterfullerene C60 provides experimental evidence for the importance of attractive concave−convex π−π interactions in the supramolecular chemistry of fullerenes with buckybowls. An association constant of 8600 ± 500 M-1 was estimated for the complex formation by NMR titration experiment in toluene-d8.