Electrochemical ring-contraction synthesis of [60]fullerene-fused indanes from [60]fullerene-fused tetrahydroisoquinolines

Abstract

A method was developed for the synthesis of [60]fullerene-fused indanes via an electrochemically triggered, trace-oxygen-mediated ring contraction of [60]fullerene-fused tetrahydroisoquinolines, followed by direct functionalization at the nitrogen atom with trifluoroacetic acid or electrophiles. This method represents a new skeletal editing strategy for converting [60]fullerene-fused tetrahydroisoquinolines directly into indanes. The structures of the products were unambiguously determined by spectroscopic and single-crystal X-ray crystallographic analyses. In addition, a synthesized indane derivative was applied as a third component in organic solar cells, enhancing photovoltaic performance.