Subphthalocyanine fused dimers–C60 dyads: synthesis, characterization, and theoretical study

A donor–acceptor covalently linked dyad consisting of a subphthalocyanine fused dimer unit doubly-connected to a [60]fullerene has been prepared through double cycloaddition of the fused dimer, previously functionalized with aldehyde groups in the axial positions, to the fullerene (1,3-dipolar cycloaddition of azomethine ylides). The compound, isolated in several fractions, has been characterized and studied employing photophysical and electrochemical techniques. Molecular modeling of the distinct possible isomers was carried out using semiempirical methods.