Carborane-stilbene dyads: the influence of substituents and cluster isomers on photoluminescence properties

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dc.contributor.authorCabrera González, Justo Enrique
dc.contributor.authorJuárez-Pérez, E. J.
dc.contributor.authorTeixidor, F.
dc.contributor.authorPérez-Inestrosa, E.
dc.contributor.authorMontenegro, J. M.
dc.contributor.authorSillanpää, R.
dc.contributor.authorHaukkad, M.
dc.contributor.authorNúñez, R.
dc.date.accessioned2024-01-30T09:24:49Z
dc.date.available2024-01-30T09:24:49Z
dc.date.issued2016-12-13
dc.description.abstractTwo novel styrene-containing meta-carborane derivatives substituted at the second carbon cluster atom (Cc) with either a methyl (Me) or a phenyl (Ph) group are introduced herein along with a new set of stilbene-containing ortho- (o-) and meta- (m-) carborane dyads. The latter set of compounds have been prepared from styrene-containing carborane derivatives via a Heck coupling reaction. High regioselectivity has been achieved for these compounds by using a combination of palladium complexes [Pd2(dba)3]/[Pd(t-Bu3P)2] as a catalytic system, yielding exclusively E isomers. All compounds have been fully characterised and the crystal structures of seven of them were analysed by X-ray diffraction. The absorption spectra of these compounds are similar to those of their respective fluorophore groups (styrene or stilbene), showing a very small influence of the substituent (Me or Ph) linked to the second Cc atom or the cluster isomer (o- or m-). On the other hand, fluorescence spectroscopy revealed high emission intensities for Me-o-carborane derivatives, whereas their Ph-o-carborane analogues evidenced an almost total lack of fluorescence, confirming the significant role of the substituent bound to the adjacent Cc in o-carboranes. In contrast, all the m-carborane derivatives display similar photoluminescence (PL) behavior regardless of the substituent attached to the second Cc, demonstrating its small influence on emission properties. Additionally, m-carborane derivatives are significantly more fluorescent than their o-counterparts, reaching quantum yield values as high as 30.2%. Regarding solid state emission, only stilbene-containing Ph-o-carborane derivatives, which showed very low fluorescence in solution, exhibited notable PL emission in films attributed to aggregation-induced emission. DFT calculations were performed to successfully complement the photoluminescence studies, supporting the experimentally observed photophysical behavior of the styrene and stilbene-containing carborane derivatives. In conclusion, in this work it is proved that it is possible to tailor the PL properties of carborane-stilbene dyads by changing the Cc substituent and the carborane isomer.
dc.description.departmentDepto. de Química en Ciencias Farmacéuticas
dc.description.facultyFac. de Farmacia
dc.description.refereedTRUE
dc.description.sponsorshipMinisterio de Economía y Competitividad (España)
dc.description.sponsorshipGeneralitat de Catalunya
dc.description.sponsorship“Severo Ochoa” Program for Centers of Excellence in R&D
dc.description.statuspub
dc.identifier.citationFerrer-Ugalde A, Cabrera-González J, Juárez-Pérez EJ, Teixidor F, Pérez-Inestrosa E, Montenegro JM, et al. Carborane–stilbene dyads: the influence of substituents and cluster isomers on photoluminescence properties. Dalton Trans 2017;46:2091–104. https://doi.org/10.1039/C6DT04003A.
dc.identifier.doi10.1039/C6DT04003A
dc.identifier.essn1477-9234
dc.identifier.issn1477-9226
dc.identifier.officialurlhttps://doi.org/10.1039/C6DT04003A
dc.identifier.urihttps://hdl.handle.net/20.500.14352/96355
dc.journal.titleDalton Transactions
dc.language.isoeng
dc.page.final2104
dc.page.initial2091
dc.publisherRoyal Society of Chemistry
dc.relation.projectIDinfo:eu-repo/grantAgreement/MINECO/CTQ2013-44670-R
dc.relation.projectIDinfo:eu-repo/grantAgreement/MINECO/CTQ2013-41339-P
dc.relation.projectIDinfo:eu-repo/grantAgreement/2014/SGR/149
dc.relation.projectIDinfo:eu-repo/grantAgreement/SEV-2015-0496
dc.rights.accessRightsrestricted access
dc.subject.ucmQuímica
dc.subject.unesco23 Química
dc.titleCarborane-stilbene dyads: the influence of substituents and cluster isomers on photoluminescence properties
dc.typejournal article
dc.volume.number46
dspace.entity.typePublication
relation.isAuthorOfPublication5fdca92d-6eb3-4245-bdfe-1bf73af9881b
relation.isAuthorOfPublication.latestForDiscovery5fdca92d-6eb3-4245-bdfe-1bf73af9881b
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