Manipulating Charge-TransferStates in BODIPYs: A ModelStrategy to Rapidly Develop Photodynamic Theragnostic Agents
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2020
Authors
Jiménez González, Josué
Prieto Montero, Ruth
Ortíz García, María Josefa
Oliden Sánchez, Ainhoa
López Arbeloa, Íñigo María
Martínez Martínez, Virginia
Moya Cerero, Santiago de la
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Wiley
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Abstract
On the basis of a family of BINOL (1,1′-bi-2-naphthol)-based O-BODIPY (dioxyboron dipyrromethene) dyes, it is demonstrated that chemical manipulation of the chromophoric push–pull character, by playing with the electron-donating capability of the BINOL moiety (BINOL versus 3,3'-dibromoBINOL) and with the electron-acceptor ability of the BODIPY core (alkyl substitution degree), is a workable strategy to finely balance fluorescence (singlet-state emitting action) versus the capability to photogenerate cytotoxic reactive oxygen species (triplet-state photosensitizing action). It is also shown that the promotion of a suitable charge-transfer character in the involved chromophore upon excitation enhances the probability of an intersystem crossing phenomenon, which is required to populate the triple state enabling singlet oxygen production. The reported strategy opens up new perspectives for rapid development of smarter agents for photodynamic theragnosis, including heavy-atom-free agents, from a selected organic fluorophore precursor.