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

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dc.contributor.authorPalao Utiel, Eduardo
dc.contributor.authorSola Llano, Rebeca
dc.contributor.authorTabero Truchado, Andrea
dc.contributor.authorManzano, Hegoi
dc.contributor.authorRodríguez Agarrabeitia, Antonia
dc.contributor.authorVillanueva Oroquieta, Ángeles
dc.contributor.authorLópez Arbeloa, Íñigo María
dc.contributor.authorMartínez Martínez, Virginia
dc.contributor.authorOrtíz García, María Josefa
dc.date.accessioned2023-06-17T22:09:31Z
dc.date.available2023-06-17T22:09:31Z
dc.date.issued2017-07-26
dc.descriptionManuscript Received: 24 MAR 2017; Accepted manuscript online: 19 MAY 2017; Version of Record online: 6 JUL 2017; Issue online: 26 JUL 2017
dc.description.abstractBiscyclometalated 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
dc.description.departmentSección Deptal. de Química Orgánica (Óptica y Optometría)
dc.description.facultyFac. de Óptica y Optometría
dc.description.refereedTRUE
dc.description.sponsorshipMinisterio de Economía y Competitividad (MINECO)
dc.description.sponsorshipMinisterio de Ciencia e Innovación (MICINN)
dc.description.sponsorshipComunidad de Madrid
dc.description.sponsorshipGobierno vasco (España)
dc.description.statuspub
dc.eprint.idhttps://eprints.ucm.es/id/eprint/44994
dc.identifier.doi10.1002/chem.201701347
dc.identifier.issn0947-6539
dc.identifier.officialurlhttp://dx.doi.org/10.1002/chem.201701347
dc.identifier.relatedurlhttp://onlinelibrary.wiley.com/wol1/doi/10.1002/chem.201701347/full
dc.identifier.relatedurlhttps://www.researchgate.net/publication/317190378_AcetylacetonateBODIPY-Biscyclometalated_IridiumIII_Complexes_Effective_Strategy_towards_Smarter_Fluorescent_Photosensitizer_Agents
dc.identifier.urihttps://hdl.handle.net/20.500.14352/18149
dc.issue.number42
dc.journal.titleChemistry: a european journal
dc.language.isoeng
dc.page.final10147
dc.page.initial10139
dc.publisherWiley
dc.relation.projectIDMAT2014-51937-C-2-P
dc.relation.projectIDMAT2014-51937-C-3-P
dc.relation.projectIDMAT2015-68837-REDT
dc.relation.projectIDCTQ2013-48767-C3-3-R
dc.relation.projectIDNANOFRONTMAG- CM (S2013/MIT-2850)
dc.relation.projectIDIT912-16
dc.relation.projectIDRYC-2011-09505
dc.rights.accessRightsrestricted access
dc.subject.cdu547.1
dc.subject.cdu543.426
dc.subject.keywordBODIPY
dc.subject.keywordFluorescent probes
dc.subject.keywordIridium (III) complexes
dc.subject.keywordPhotodynamic therapy
dc.subject.keywordSinglet oxygen
dc.subject.ucmQuímica orgánica (Química)
dc.subject.unesco2306 Química Orgánica
dc.titleAcetylacetonateBODIPY-Biscyclometalated Iridium(III) Complexes: Effective Strategy towards Smarter Fluorescent Photosensitizer Agents
dc.typejournal article
dc.volume.number23
dspace.entity.typePublication
relation.isAuthorOfPublication0486160c-3df6-4270-bf91-3e96cd33d85d
relation.isAuthorOfPublication.latestForDiscovery0486160c-3df6-4270-bf91-3e96cd33d85d
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