Complexation of Fullerenes by Subphthalocyanine Dimers

Abstract

Tweezer-like molecules comprised of two boron subphthalocyanine (SubPc) units were prepared by Sonogashira couplings and investigated using NMR spectroscopy for their ability to bind fullerenes (C₆₀ and C₇₀). The preorganization of the tweezers provided association constants of ca. 10³ M^-1 in toluene- d₈, while a SubPc monomer did not show any association. Nevertheless, the SubPc monomer crystallized with the fullerenes as 2:1 complexes, supporting the favorable tweezer-like design for complexation, which was further corroborated by computations.