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

Abstract

The synthesis of [60]fullerene-fused indanes was developed 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. The present method is a new skeletal editing strategy to convert [60]fullerene-fused tetrahydroisoquinolines directly to indanes. The structures of the products were unambiguously determined by spectroscopic data and single-crystal X-ray crystallographic analysis. In addition, a synthesized indane derivative was applied as a third component in organic solar cells, enhancing photovoltaic performance.