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dc.contributorUniversitat Ramon Llull. IQS
dc.contributor.authorNonell, Santi
dc.contributor.authorGandioso, Albert
dc.contributor.authorContreras, Sara
dc.contributor.authorMelnyk, Ivanna
dc.contributor.authorOliva, Javier
dc.contributor.authorVelasco Castrillo, Dolores
dc.contributor.authorGarcia Amorós, Jaume
dc.contributor.authorMarchán Sancho, Vicente
dc.date.accessioned2020-07-07T14:23:04Z
dc.date.accessioned2023-07-13T05:44:00Z
dc.date.available2020-07-07T14:23:04Z
dc.date.available2023-07-13T05:44:00Z
dc.date.issued2017-05
dc.identifier.urihttp://hdl.handle.net/20.500.14342/1011
dc.description.abstractWe report the design, synthesis, and spectroscopic characterization of a series of push–pull chromophores based on a novel coumarin scaffold in which the carbonyl of the lactone function of the original coumarin dyes has been replaced by the cyano(4-nitrophenyl)methylene moiety. The skeleton of the compounds was synthesized by condensation of a thiocoumarin precursor with the corresponding arylacetonitrile derivatives, and their photophysical properties were fine-tuned through the incorporation of electron-withdrawing groups (EWGs) like nitro and cyano at the phenyl ring, leading to absorption in the green to red region. Although fluorescence emission was weakened or even canceled upon introduction of two or three strong EWGs, the emission of the mononitro-containing coumarin derivatives in the red region upon excitation with green light is noticeable, as are their significantly large Stokes shifts. The new coumarin derivatives can be useful as photocleavable protecting groups, as demonstrated through the synthesis and characterization of a series of coumarin-based photocages of benzoic acid. Preliminary photolysis studies with green light have demonstrated that the structure of the coumarin chromophore influences the rate of the uncaging process, opening the way to exploiting these new coumarin scaffolds as caging groups that can be removed with visible light.eng
dc.format.extent29 p.
dc.language.isoeng
dc.publisherAmerican Chemical Society
dc.relation.ispartofJournal of Organic Chemistry. Vol.82, n.10 (2017), p.5398-5408
dc.rights© American Chemical Society. Tots els drets reservats
dc.sourceRECERCAT (Dipòsit de la Recerca de Catalunya)
dc.subject.otherÀcid benzoic
dc.subject.otherFotoquímica
dc.subject.otherCumarines
dc.subject.otherPhotochemistry
dc.subject.otherChromophores
dc.subject.otherLight
dc.subject.otherBenzoic acid
dc.subject.otherNuclear magnetic resonance spectroscopy
dc.titleDevelopment of green/red-absorbing chromophores based on a coumarin scaffold that are useful as caging groups
dc.typeinfo:eu-repo/semantics/article
dc.typeinfo:eu-repo/semantics/acceptedVersion
dc.rights.accessLevelinfo:eu-repo/semantics/openAccess
dc.embargo.termscap
dc.subject.udc547
dc.identifier.doihttps://doi.org/10.1021/acs.joc.7b00788


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