2026-06-01T01:30:05Zhttps://docta.ucm.es/rest/oai/request

oai:docta.ucm.es:20.500.14352/969162024-08-10T00:01:46Zcom_20.500.14352_14col_20.500.14352_15

Chlorinated BODIPYs: Surprisingly Efficient and Highly Photostable Laser Dyes Durán Sampedro, Gonzalo Rodríguez Agarrabeitia, Antonia García Moreno, Inmaculada Costela, Angel Bañuelos, Jorge Arbeloa, Teresa López Arbeloa, Iñigo Chiara, Jose Luis Ortiz García, María Josefa 547 Chlorinated BODIPY Dye halogenation Chlorination Photophysics Regioselectivity Química orgánica (Química) 23 Química A 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> Ministerio de Economía, Comercio y Empresa (España) European Commission Eusko Jaurlaritza Depto. de Química Orgánica Fac. de Ciencias Químicas TRUE pub 2024-01-31T09:17:00Z 2024-01-31T09:17:00Z 2012 journal article VoR https://hdl.handle.net/20.500.14352/96916 1434-193X 10.1002/ejoc.201200946 1099-0690 eng info:eu-repo/grantAgreement/MICINN//MAT2010-20646-C04-01/ES/NUEVOS SISTEMAS FOTOSENSIBILIZADOS CONTENIENDO NANOESTRUCTURAS PARA APLICACIONES LASER Y BIOFOTONICAS/ info: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/ info:eu-repo/grantAgreement/MICINN//MAT2010-20646-C04-03/ES/SINTESIS Y CARACTERIZACION DE NANOPARTICULAS HIBRIDAS FOTOSENSIBILIZADAS. APLICACION EN BIORECONOCIMIENTO Y LASER/ info: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/ TRACE 2009-0144 info:eu-repo/grantAgreement/CAM//S2009%2FPPQ-1634/ES/Desarrollo de métodos catalíticos altamente eficientes/ IT339-10 Durán 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. restricted access application/pdf Wiley