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- Title
Porphyrin as a versatile visible-light-activatable organic/metal hybrid photoremovable protecting group.
- Authors
Sekhar, Adiki Raja; Chitose, Youhei; Janoš, Jiří; Dangoor, Sahar Israeli; Ramundo, Andrea; Satchi-Fainaro, Ronit; Slavíček, Petr; Klán, Petr; Weinstain, Roy
- 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. 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.
- Subjects
PORPHYRINS; CHEMICAL properties; CHEMICAL potential; METAL ions; METALS
- Publication
Nature Communications, 2022, Vol 13, Issue 1, p1
- ISSN
2041-1723
- Publication type
Article
- DOI
10.1038/s41467-022-31288-2