Synthesis and Photophysical Properties of Hexabenzocoronene‐Tetrabenzoporphyrin Architectures

Abstract

Porphyrin‐based architectures have emerged as excellent candidates for artificial light‐harvesting antennae. Although tetrabenzoporphyrins (TBPs), the π ‐extended “bigger brothers” of porphyrins, benefit from increased absorptivity in the near‐infrared (NIR), their utilization in light‐harvesting systems is still in its infancy. Within this work, we prepared two donor‐acceptor hetero dyads consisting of hexa‐ peri ‐hexabenzocoronenes (HBCs) to harvest high energetic near‐UV light, and a TBP core, which serves as visible to NIR light antenna and as subsequent energy sink of the conjugate. The HBCs are either attached to the meso ‐position or via a maleimide‐bridge on the periphery of the macrocycle. Upon excitation of the HBC moieties, both dyads exhibit an efficient energy transfer to the TBP core. Furthermore, the TBP‐HBC dyads show superior light‐harvesting properties compared to the respective HBC‐porphyrin reference and the naturally occurring chlorophylls a/b.