RT Journal Article
T1 Rational Design of Advanced Photosensitizers Based on Orthogonal BODIPY Dimers to Finely Modulate Singlet Oxygen Generation
A1 Epelde Elezcano, Nerea
A1 Palao Utiel, Eduardo
A1 Manzano, Hegoi
A1 Prieto Castañeda, Alejandro
A1 Rodríguez Agarrabeitia, Antonia
A1 Tabero Truchado, Andrea
A1 Villanueva Oroquieta, Ángeles
A1 Moya Cerero, Santiago de la
A1 López Arbeloa, Íñigo María
A1 Martínez Martínez, Virginia
A1 Ortiz García, María Josefa
AB 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).
PB Wiley
SN 0947-6539
YR 2017
FD 2017-04-06
LK https://hdl.handle.net/20.500.14352/18157
UL https://hdl.handle.net/20.500.14352/18157
LA eng
NO Manuscript Received: 14 DEC 2016; Accepted manuscript online: 6 FEB 2017; Version of Record online: 21 MAR 2017; Issue online: 10 APR 2017
NO Ministerio de Ciencia e Innovación (MICINN)
NO Ministerio de Economía y Competitividad (MINECO)
NO Comunidad de Madrid
NO Gobierno Vasco
DS Docta Complutense
RD 20 dic 2025