Chlorinated BODIPYs: Surprisingly Efficient and Highly Photostable Laser Dyes

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dc.contributor.authorDurán Sampedro, Gonzalo
dc.contributor.authorRodríguez Agarrabeitia, Antonia
dc.contributor.authorGarcía Moreno, Inmaculada
dc.contributor.authorCostela, Angel
dc.contributor.authorBañuelos, Jorge
dc.contributor.authorArbeloa, Teresa
dc.contributor.authorLópez Arbeloa, Iñigo
dc.contributor.authorChiara, Jose Luis
dc.contributor.authorOrtiz García, María Josefa
dc.date.accessioned2024-01-31T09:17:00Z
dc.date.available2024-01-31T09:17:00Z
dc.date.issued2012
dc.description.abstractA series of mono‐ to hexachlorinated BODIPY dyes have been prepared in good to excellent yields through the use of chlorosuccinimide as an inexpensive halogenating reagent. This library of chlorinated dyes allowed analysis in detail, from the experimental and theoretical points of view, of the dependency of the photophysical and optical properties of the dyes on the number and positions of the chlorine substituents on their BODIPY cores. Quantum mechanical calculations predict the regioselectivity of the halogenation reaction and explain why some positions are less prone to chlorination. The new chlorinated BODIPYs exhibit enhanced laser action with respect to their non‐halogenated analogues, both in liquid solution and in the solid phase. In addition, chlorination is a facile and essentially costless protocol for overcoming important shortcomings exhibited by commercially available BODIPYs, which should favor their practical applications in optical and sensing fields.</jats:p>en
dc.description.departmentDepto. de Química Orgánica
dc.description.facultyFac. de Ciencias Químicas
dc.description.refereedTRUE
dc.description.sponsorshipMinisterio de Economía, Comercio y Empresa (España)
dc.description.sponsorshipEuropean Commission
dc.description.sponsorshipEusko Jaurlaritza
dc.description.statuspub
dc.identifier.citationDurán Sampedro, G., Rodríguez Agarrabeitia, A., García Moreno, I. et al. «Chlorinated BODIPYs: Surprisingly Efficient and Highly Photostable Laser Dyes». European Journal of Organic Chemistry, vol. 2012, n.o 32, noviembre de 2012, pp. 6335-50. https://doi.org/10.1002/ejoc.201200946.
dc.identifier.doi10.1002/ejoc.201200946
dc.identifier.essn1099-0690
dc.identifier.issn1434-193X
dc.identifier.officialurlhttps://doi.org/10.1002/ejoc.201200946
dc.identifier.relatedurlhttps://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/ejoc.201200946
dc.identifier.urihttps://hdl.handle.net/20.500.14352/96916
dc.journal.titleEuropean Journal of Organic Chemistry
dc.language.isoeng
dc.page.final6350
dc.page.initial6335
dc.publisherWiley
dc.relation.projectIDinfo:eu-repo/grantAgreement/MICINN//MAT2010-20646-C04-01/ES/NUEVOS SISTEMAS FOTOSENSIBILIZADOS CONTENIENDO NANOESTRUCTURAS PARA APLICACIONES LASER Y BIOFOTONICAS/
dc.relation.projectIDinfo:eu-repo/grantAgreement/MICINN//MAT2010-20646-C04-02/ES/DISEÑO, SINTESIS Y CARACTERIZACION DE NUEVOS COLORANTES ORGANICOS CON EMISION EN LA REGION ESPECTRAL DEL AZUL, ROJO E IR CERCANO, PARA APLICACIONES AVANZADAS/
dc.relation.projectIDinfo:eu-repo/grantAgreement/MICINN//MAT2010-20646-C04-03/ES/SINTESIS Y CARACTERIZACION DE NANOPARTICULAS HIBRIDAS FOTOSENSIBILIZADAS. APLICACION EN BIORECONOCIMIENTO Y LASER/
dc.relation.projectIDinfo:eu-repo/grantAgreement/MICINN//MAT2010-20646-C04-04/ES/CARACTERIZACION FOTOFISICA Y MODELIZACION CUANTICA DE COLORANTES LASER EN MEDIO HOMOGENEOS, MATERIALES NANOMETRICOS Y ENCAPSULADOS EN NANOCANALES/
dc.relation.projectIDTRACE 2009-0144
dc.relation.projectIDinfo:eu-repo/grantAgreement/CAM//S2009%2FPPQ-1634/ES/Desarrollo de métodos catalíticos altamente eficientes/
dc.relation.projectIDIT339-10
dc.rights.accessRightsrestricted access
dc.subject.cdu547
dc.subject.keywordChlorinated BODIPY
dc.subject.keywordDye halogenation
dc.subject.keywordChlorination
dc.subject.keywordPhotophysics
dc.subject.keywordRegioselectivity
dc.subject.ucmQuímica orgánica (Química)
dc.subject.unesco23 Química
dc.titleChlorinated BODIPYs: Surprisingly Efficient and Highly Photostable Laser Dyesen
dc.typejournal article
dc.type.hasVersionVoR
dc.volume.number32
dspace.entity.typePublication
relation.isAuthorOfPublication24ec8912-4d0c-471c-9c44-49d62a79827a
relation.isAuthorOfPublication0486160c-3df6-4270-bf91-3e96cd33d85d
relation.isAuthorOfPublication07f337af-8a30-4929-81db-4e92176e5c87
relation.isAuthorOfPublication.latestForDiscovery07f337af-8a30-4929-81db-4e92176e5c87
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