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

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Authors

SEKHAR Adiki Raja CHITOSE Youhei JANOS Jiri DANGOOR Sahar Israeli RAMUNDO Andrea SATCHI-FAINARO Ronit SLAVÍČEK Petr KLÁN Petr WEINSTAIN Roy

Year of publication 2022
Type Article in Periodical
Magazine / Source Nature Communications
MU Faculty or unit

Faculty of Science

Citation
Web https://www.nature.com/articles/s41467-022-31288-2
Doi http://dx.doi.org/10.1038/s41467-022-31288-2
Keywords OXYGEN QUANTUM YIELDS; SINGLET OXYGEN; EXCITED-STATES; TRANSIENT ABSORPTION; MECHANISMS; DYNAMICS; SPECTRA; BODIPY; PHOTOSENSITIZERS; LUMINESCENCE
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Description Photoremovable protecting groups (PPGs) represent one of the main contemporary implementations of photochemistry. Here, the authors show that meso-methylporphyrin unites traditionally exclusive features of organic and metal-complex PPGs within a single entity. 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.
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