A facile and high-yield formation of dipyrrin-boronic acid dyads and triads: a light-harvesting system in the visible region based on the efficient energy transfer

Abstract

Artificial light-harvesting systems, Ar,O-BODIPY dyads and triads conjugated with a light harvester, were synthesized in high yield by the reaction of an N₂O₂-type dipyrrin with boronic acids. Dyad 2 having a pyrene unit underwent quantitative Förster resonance energy transfer (FRET) from the antenna unit, pyrene, to the fluorophore unit, Ar,O-BODIPY. Triads 3·5 and 4·5 were quantitatively prepared by mixing pyridine-appended compounds 3 and 4 with saloph·Zn complex 5, respectively. Triad 4·5 underwent efficient FRET from the saloph·Zn complex unit to the fluorophore unit at the rate of 2.0 × 10¹¹ s⁻¹. Interestingly, the fluorescence quenching process in the excited state of the triad 3·5 took place following the energy transfer event. Thus, appropriate positioning of the energy donor and acceptor is necessary to construct a highly efficient FRET system.