Manipulating Charge-TransferStates in BODIPYs: A ModelStrategy to Rapidly Develop Photodynamic Theragnostic Agents

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Jiménez González, Josué and Prieto Montero, Ruth and Lora Maroto, Beatriz and Moreno Jiménez, Florencio and Ortíz García, María Josefa and Oliden Sánchez, Ainhoa and López Arbeloa, Íñigo María and Martínez Martínez, Virginia and Moya Cerero, Santiago de la (2020) Manipulating Charge-TransferStates in BODIPYs: A ModelStrategy to Rapidly Develop Photodynamic Theragnostic Agents. Chemistry: a european journal, 26 (3). pp. 601-605. ISSN 0947-6539; E-ISSN: 1521-3765

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Official URL: https://doi.org/10.1002/chem.201904257




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.


Item Type:Article
Subjects:Sciences > Chemistry > Chemistry, Organic
Medical sciences > Medicine > Biochemistry
Medical sciences > Optics > Imaging systems
ID Code:69717
Deposited On:01 Jul 2022 12:29
Last Modified:05 Jul 2022 08:01

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