Synthesis and Photophysical Properties of Hexabenzocoronene‐Tetrabenzoporphyrin Architectures

Michael Ruppel; Lampros‐Pascal Gazetas; Dominik Lungerich; Norbert Jux

doi:10.1002/ejoc.202000860

journal article Open Access Aug 20, 2020

Synthesis and Photophysical Properties of Hexabenzocoronene‐Tetrabenzoporphyrin Architectures

Michael Ruppel

Lampros‐Pascal Gazetas

Dominik Lungerich

Norbert Jux

European Journal of Organic Chemistry Vol. 2020 No. 40 pp. 6352-6360 · Wiley

View at Publisher Save 10.1002/ejoc.202000860

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.

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Details

Published: Aug 20, 2020
Vol/Issue: 2020(40)
Pages: 6352-6360
License: View

Authors

M

Michael Ruppel

Department of Chemistry and Pharmacy & Interdisciplinary Center for Molecular Materials (ICMM) Friedrich‐Alexander University Erlangen‐Nuremberg Nikolaus‐Fiebiger‐Str. 10 91058 Erlangen Germany

L

Lampros‐Pascal Gazetas

Department of Chemistry and Pharmacy & Interdisciplinary Center for Molecular Materials (ICMM) Friedrich‐Alexander University Erlangen‐Nuremberg Nikolaus‐Fiebiger‐Str. 10 91058 Erlangen Germany

D

Dominik Lungerich

Institute for Basic Science (IBS), 50 Yonsei‐ro, Seodaemun‐gu Center for Nanomedicine 03722 Seoul Republic of Korea; Graduate Program of Nano Biomedical Engineering (NanoBME) Advanced Science Institute Yonsei University 03722 Seoul Republic of Korea

N

Norbert Jux

Department of Chemistry and Pharmacy & Interdisciplinary Center for Molecular Materials (ICMM) Friedrich‐Alexander University Erlangen‐Nuremberg Nikolaus‐Fiebiger‐Str. 10 91058 Erlangen Germany

Funding

DFG Award: 182849149

Institute for Basic Science Award: IBS.R026-Y1

Cite This Article

Michael Ruppel, Lampros‐Pascal Gazetas, Dominik Lungerich, et al. (2020). Synthesis and Photophysical Properties of Hexabenzocoronene‐Tetrabenzoporphyrin Architectures. European Journal of Organic Chemistry, 2020(40), 6352-6360. https://doi.org/10.1002/ejoc.202000860

Synthesis and Photophysical Properties of Hexabenzocoronene‐Tetrabenzoporphyrin Architectures

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