Porphyrin as a versatile visible-light-activatable organic/metal hybrid photoremovable protecting group

Adiki Raja Sekhar, Youhei Chitose, Jiří Janoš, Sahar Israeli Dangoor, Andrea Ramundo, Ronit Satchi-Fainaro, Petr Slavíček, Petr Klán () and Roy Weinstain ()
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Adiki Raja Sekhar: Tel-Aviv University
Youhei Chitose: Masaryk University
Jiří Janoš: University of Chemistry and Technology, Prague
Sahar Israeli Dangoor: Tel Aviv University
Andrea Ramundo: Masaryk University
Ronit Satchi-Fainaro: Tel Aviv University
Petr Slavíček: University of Chemistry and Technology, Prague
Petr Klán: Masaryk University
Roy Weinstain: Tel-Aviv University

Nature Communications, 2022, vol. 13, issue 1, 1-11

Abstract: Abstract Photoremovable protecting groups (PPGs) represent one of the main contemporary implementations of photochemistry in diverse fields of research and practical applications. For the past half century, organic and metal-complex PPGs were considered mutually exclusive classes, each of which provided unique sets of physical and chemical properties thanks to their distinctive structures. Here, we introduce the meso-methylporphyrin group as a prototype hybrid-class PPG that unites traditionally exclusive elements of organic and metal-complex PPGs within a single structure. We show that the porphyrin scaffold allows extensive modularity by functional separation of the metal-binding chromophore and up to four sites of leaving group release. The insertion of metal ions can be used to tune their spectroscopic, photochemical, and biological properties. We provide a detailed description of the photoreaction mechanism studied by steady-state and transient absorption spectroscopies and quantum-chemical calculations. Our approach applied herein could facilitate access to a hitherto untapped chemical space of potential PPG scaffolds.

Date: 2022
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DOI: 10.1038/s41467-022-31288-2

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