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Manipulating Charge-Transfer States in BODIPYs: A Model Strategy to Rapidly Develop Photodynamic Theragnostic Agents |
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| Authors: | Josué Jiménez Ruth Prieto-Montero Prof. Beatriz L. Maroto Prof. Florencio Moreno Prof. María J. Ortiz Ainhoa Oliden-Sánchez Prof. Iñigo López-Arbeloa Prof. Virginia Martínez-Martínez Prof. Santiago de la Moya |
| Affiliation: | 1. Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Ciudad Universitaria s/n, 28040 Madrid, Spain These authors contributed equally to this work.;2. Departamento de Química Física, Facultad de Ciencia y Tecnología, Universidad del País Vasco, 48080 Bilbao, Spain These authors contributed equally to this work.;3. Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Ciudad Universitaria s/n, 28040 Madrid, Spain;4. Departamento de Química Física, Facultad de Ciencia y Tecnología, Universidad del País Vasco, 48080 Bilbao, Spain |
| 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. |
| Keywords: | charge transfer photodynamic therapy singlet oxygen theragnosis triplet modulation |