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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 and Palao Utiel, Eduardo and Manzano, Hegoi and Prieto Castañeda, Alejandro and Rodríguez Agarrabeitia, Antonia and Tabero Truchado, Andrea and Villanueva Oroquieta, Ángeles and Moya Cerero, Santiago de la and López Arbeloa, Íñigo María and Martínez Martínez, Virginia and 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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Official URL: https://doi.org/10.1002/chem.201605822




Abstract

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).


Item Type:Article
Additional Information:

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

Uncontrolled Keywords:Biological activity; Charge transfer; Singlet oxygen; Solvent effects; Substituent effects
Subjects:Sciences > Physics > Particles
Sciences > Chemistry > Optics
Sciences > Chemistry > Chemistry, Organic
ID Code:45053
Deposited On:10 Oct 2017 09:08
Last Modified:11 Oct 2017 08:48

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