Novel chlorin–diene building block by enyne metathesis: synthesis of chlorin–fullerene dyads

Abstract

The first example demonstrating the utility of enyne metathesis in preparing a chlorin–diene system as a novel and versatile building block is discussed; Diels–Alder reaction [4 + 2] of the diene with fullerene (C₆₀) produced the chlorin–fullerene dyad, a new artificial photosynthetic model; compared to the non-fullerene analogs, the corresponding free base and Zn^II chlorin–C₆₀ dyads showed a remarkable decrease in their fluorescence intensity, indicating a rapid quenching of the chlorin excited singlet state by the fullerene moiety.