Regio- and stereo-selective intermolecular [2+2] cycloaddition of allenol esters with C60 leading to alkylidenecyclobutane-annulated fullerenes

Abstract

The intermolecular [2+2] cycloaddition of allenol esters, which were in situ generated by Pt-catalyzed 1,3-acyloxy migration of propargylic esters, with C₆₀ proceeded regio- and stereo-selectively to give a novel class of alkylidenecyclobutane-annulated fullerenes. The cyclobutane-annulated fullerene derivatives have high-lying LUMO levels, which gave a high open-circuit voltage in organic solar cell applications. The observed high electron mobility provided a good fill factor compared with the PCBM-based devices.