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, Roy Weinstain

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Article number3614
JournalNature Communications
Volume13
Issue number1
DOIs
StatePublished - Dec 2022

Fingerprint

Dive into the research topics of 'Porphyrin as a versatile visible-light-activatable organic/metal hybrid photoremovable protecting group'. Together they form a unique fingerprint.

Cite this