Bis-corannulenoanthracene: An Angularly Fused Pentacene as a Precursor for Barrelene-Tethered Receptors for Fullerenes

Bis-corannulenoanthracene (C50H22, 5) was prepared by the Diels–Alder
double cycloaddition
of iso­corannuleno­furan with “bis-benzyne”,
followed by deoxygenation of the adducts. Despite the presence of
a pentacene core, 5 is stable enough to be isolated and
stored. A cycloaddition reaction of 5 with maleic anhydride
produces 10 which exhibits strong affinity toward C60, as evidenced by 1H NMR titration experiment.
Synthesis of 10 demonstrates the synthetic utility of
hydrocarbon 5 in the preparation of the barrelene-based
molecular clips with two benzocorannulene pincers adorned with polar
substituents on their tethers, which will allow for immobilization
of the receptors on solid supports.