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 (1)H 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.
Department of Chemistry, Mississippi State University , Mississippi State, Mississippi 39762, United States.
K G Upul R
KG
Kumarasinghe
Department of Chemistry, Louisiana State University , Baton Rouge, Louisiana 70803, United States.
Frank R
FR
Fronczek
Department of Chemistry, Mississippi State University , Mississippi State, Mississippi 39762, United States.
Henry U
HU
Valle
Department of Chemistry, Mississippi State University , Mississippi State, Mississippi 39762, United States.
Andrzej
A
Sygula