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Synthesis and Photophysical Properties of Hexabenzocoronene‐Tetrabenzoporphyrin Architectures
Author(s) -
Ruppel Michael,
Gazetas LamprosPascal,
Lungerich Dominik,
Jux Norbert
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000860
Subject(s) - chemistry , porphyrin , photochemistry , maleimide , energy transfer , fluorescence , acceptor , conjugate , polymer chemistry , chemical physics , mathematical analysis , physics , mathematics , condensed matter physics , quantum mechanics
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.