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AcetylacetonateBODIPY-Biscyclometalated Iridium(III) Complexes: Effective Strategy towards Smarter Fluorescent Photosensitizer Agents

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Palao Utiel, Eduardo and Sola Llano, Rebeca and Tabero Truchado, Andrea and Manzano, Hegoi and Rodríguez Agarrabeitia, Antonia and Villanueva Oroquieta, Ángeles and López Arbeloa, Íñigo María and Martínez Martínez, Virginia and Ortíz García, María Josefa (2017) AcetylacetonateBODIPY-Biscyclometalated Iridium(III) Complexes: Effective Strategy towards Smarter Fluorescent Photosensitizer Agents. Chemistry: a european journal, 23 (42). pp. 10139-10147. ISSN 0947-6539

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Official URL: http://dx.doi.org/10.1002/chem.201701347




Abstract

Biscyclometalated IrIII complexes involving boron-dipyrromethene (BODIPY)-based ancillary ligands, where the BODIPY unit is grafted to different chelating cores (acetylacetonate for Ir-1 and Ir-2, and bipyridine for Ir-3) by the BODIPY meso position, have been synthesized and characterized. Complexes with the BODIPY moiety directly grafted to acetylacetonate (Ir-1 and Ir-2) exhibit higher absorption coefficients (ϵ≈4.46×104 m−1 cm−1 and 3.38×104 m−1 cm−1 at 517 nm and 594 nm, respectively), higher moderate fluorescence emission (φfl≈0.08 and 0.22 at 528 nm and 652 nm, respectively) and, in particular, more efficient singlet oxygen generation upon visible-light irradiation (φΔ≈0.86 and 0.59, respectively) than that exhibited by Ir-3 (φΔ≈0.51, but only under UV light). Phosphorescence emission, nanosecond time-resolved transient absorption, and DFT calculations suggest that BODIPY-localized long-lived 3IL states are populated for Ir-1 and Ir-2. In vitro photodynamic therapy (PDT) activity studied for Ir-1 and Ir-2 in HeLa cells shows that such complexes are efficiently internalized into the cells, exhibiting low dark- and high photocytoxicity, even at significantly low complex concentration, making them potentially suitable as theranostic agents. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim


Item Type:Article
Additional Information:

Manuscript Received: 24 MAR 2017; Accepted manuscript online: 19 MAY 2017; Version of Record online: 6 JUL 2017; Issue online: 26 JUL 2017

Uncontrolled Keywords:BODIPY; Fluorescent probes; Iridium (III) complexes; Photodynamic therapy; Singlet oxygen
Subjects:Sciences > Chemistry > Chemistry, Organic
ID Code:44994
Deposited On:06 Oct 2017 09:51
Last Modified:09 Oct 2017 07:48

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