Universidad Complutense de Madrid
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Rational Design of Advanced Photosensitizers Based on Orthogonal BODIPY Dimers to Finely Modulate Singlet Oxygen Generation

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Epelde Elezcano, Nerea y Palao Utiel, Eduardo y Manzano, Hegoi y Prieto Castañeda, Alejandro y Rodríguez Agarrabeitia, Antonia y Tabero Truchado, Andrea y Villanueva Oroquieta, Ángeles y Moya Cerero, Santiago de la y López Arbeloa, Íñigo María y Martínez Martínez, Virginia y Ortíz García, María Josefa (2017) Rational Design of Advanced Photosensitizers Based on Orthogonal BODIPY Dimers to Finely Modulate Singlet Oxygen Generation. Chemistry: a european journal, 23 (20). pp. 4837-4848. ISSN 0947-6539

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URL Oficial: https://doi.org/10.1002/chem.201605822




Resumen

The synthesis, photophysical characterization, and modeling of a new library of halogen-free photosensitizers (PS) based on orthogonal boron dipyrromethene (BODIPY) dimers are reported. Herein we establish key structural factors in order to enhance singlet oxygen generation by judiciously choosing the substitution patterns according to key electronic effects and synthetic accessibility factors. The photosensitization mechanism of orthogonal BODIPY dimers is demonstrated to be strongly related to their intrinsic intramolecular charge transfer (ICT) character through the spin-orbit charge-transfer intersystem crossing (SOCT-ISC) mechanism. Thus, singlet oxygen generation can be effectively modulated through the solvent polarity and the presence of electron-donating or withdrawing groups in one of the BODIPY units. The photodynamic therapy (PDT) activity is demonstrated by in vitro experiments, showing that selected photosensitizers are efficiently internalized into HeLa cells, exhibiting low dark toxicity and high phototoxicity, even at low PS concentration (0.05–5×10−6 m).


Tipo de documento:Artículo
Información Adicional:

Manuscript Received: 14 DEC 2016; Accepted manuscript online: 6 FEB 2017; Version of Record online: 21 MAR 2017; Issue online: 10 APR 2017

Palabras clave:Biological activity; Charge transfer; Singlet oxygen; Solvent effects; Substituent effects
Materias:Ciencias > Física > Partículas
Ciencias > Química > Optica
Ciencias > Química > Química orgánica
Código ID:45053
Depositado:10 Oct 2017 09:08
Última Modificación:11 Oct 2017 08:48

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