Formylation as a Chemical Tool to Modulate the Performance of Photosensitizers Based on Boron Dipyrromethene Dimers

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dc.contributor.authorDíaz Norambuena, Carolina
dc.contributor.authorAvellanal Zaballa, Edurne
dc.contributor.authorPrieto Castañeda, Alejandro
dc.contributor.authorBañuelos, Jorge
dc.contributor.authorde la Moya, Santiago
dc.contributor.authorRodríguez Agarrabeitia, Antonia
dc.contributor.authorMoya Cerero, Santiago De La
dc.contributor.authorOrtiz, María J.
dc.date.accessioned2024-01-11T10:56:18Z
dc.date.available2024-01-11T10:56:18Z
dc.date.issued2023-07-23
dc.description.abstractHeavy-atom-free photosensitizers are envisioned as the next generation of photoactive molecules for photo-theragnosis. In this approach, and after suitable irradiation, a single molecular scaffold is able to visualize and kill tumour cells by fluorescence signalling and photodynamic therapy (PDT), respectively, with minimal side effects. In this regard, BODIPY-based orthogonal dimers have irrupted as suitable candidates for this aim. Herein, we analyse the photophysical properties of a set of formyl-functionalized BODIPY dimers to ascertain their suitability as fluorescent photosensitizers. The conducted computationally aided spectroscopic study determined that the fluorescence/singlet oxygen generation dual performance of these valuable BODIPY dimers not only depends on the BODIPY-BODIPY linkage and the steric hindrance around it, but also can be modulated by proper formyl functionalization at specific chromophoric positions. Thus, we propose regioselective formylation as an effective tool to modulate such a delicate photonic balance in BODIPY-based dimeric photosensitizers. The taming of the excited-state dynamics, in particular intramolecular charge transfer as the key underlying process mediating fluorescence deactivation vs. intersystem crossing increasing, could serve to increase fluorescence for brighter bioimaging, enhance the generation of singlet oxygen for killing activity, or balance both for photo-theragnosis.en
dc.description.departmentSección Deptal. de Química Orgánica (Óptica y Optometría)
dc.description.facultyFac. de Óptica y Optometría
dc.description.refereedTRUE
dc.description.sponsorshipMinisterio de Ciencia, Innovación y Universidades (España)
dc.description.sponsorshipGobierno Vasco
dc.description.statuspub
dc.identifier.citationDíaz-Norambuena, C.; Avellanal-Zaballa, E.; Prieto-Castañeda, A.; Bañuelos, J.; de la Moya, S.; Agarrabeitia, A.R.; Ortiz, M.J. Formylation as a Chemical Tool to Modulate the Performance of Photosensitizers Based on Boron Dipyrromethene Dimers. Int. J. Mol. Sci. 2023, 24, 11837. h
dc.identifier.doi10.3390/ijms241411837
dc.identifier.issn1661-6596
dc.identifier.officialurlhttps://doi.org/10.3390/ijms241411837
dc.identifier.relatedurlhttps://www.mdpi.com/1422-0067/24/14/11837
dc.identifier.urihttps://hdl.handle.net/20.500.14352/92484
dc.issue.number14. Art..11837
dc.journal.titleInternational Journal of Molecular Sciences
dc.language.isoeng
dc.page.total13
dc.publisherMPDI
dc.relation.projectIDPID2020-114755GB-C32
dc.relation.projectIDPID2020-114755GB-C33
dc.relation.projectIDMCIN/AEI/10.13039/501100011033
dc.rightsAttribution 4.0 Internationalen
dc.rights.accessRightsopen access
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.subject.cdu547
dc.subject.keywordBODIPY dimers
dc.subject.keywordFluorescence
dc.subject.keywordPDT
dc.subject.keywordPhotosensitizers
dc.subject.keywordSinglet oxygen
dc.subject.knowledgeCiencias de la Salud
dc.subject.ucmQuímica orgánica (Química)
dc.subject.unesco2306 Química Orgánica
dc.titleFormylation as a Chemical Tool to Modulate the Performance of Photosensitizers Based on Boron Dipyrromethene Dimersen
dc.typejournal article
dc.type.hasVersionVoR
dc.volume.number24
dspace.entity.typePublication
relation.isAuthorOfPublication0486160c-3df6-4270-bf91-3e96cd33d85d
relation.isAuthorOfPublication7940c6e8-25c3-4083-b533-0c34e155dfa8
relation.isAuthorOfPublicationbee889c2-938d-48d9-8748-01e3c8bf5614
relation.isAuthorOfPublication.latestForDiscovery0486160c-3df6-4270-bf91-3e96cd33d85d
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