Completely regioselective, highly stereoselective formation of bisfullerene60 adducts of 6,13-dialkynyl substituted pentacenes

摘要

The reactions between fullerene[60] and two 6,13-dialkynyl substituted pentacenes are reported. As with 6,13-diaryl substituted pentacenes, fullerene[60] cycloaddition across 6,13-dialkynyl substituted pentacenes is completely regioselective and highly stereoselective. In each case, a single bisfullerene[60] adduct is formed. Because NMR spectroscopy cannot distinguish the C_(2v) cis from the C_(2h) trans structures in these cases, definitive stereochemical assignments must await X-ray structure analyses. However, by analogy to known reactions with 6,13-diaryl substituted pentacenes, a cis stereochemistry is likely for the new bisfullerene[60] adducts.