Carborane-BODIPY Dyads: New Photoluminescent Materials through an Efficient Heck Coupling

A small library of carborane-BODIPY/aza-BODIPY dyads were efficiently synthesized by means of a novel convergent synthetic approach, the key step of which is a Pd-catalyzed Heck coupling reaction. The structural characterization and photoluminescence properties of the newly synthesized dyads were ev...

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Detalles Bibliográficos
Autores: Bellomo, Chiara, Chaari, Mahdi, Cabrera González, Justo, Blangetti, Marco, Lombardi, Chiara, Deagostino, Annamaria, Viñas, Clara, Gaztelumendi, Nerea, Nogués, Carme, Núñez Aguilera, Rosario, Prandi, Cristina
Tipo de recurso: artículo
Estado:Versión enviada para evaluación y publicación
Fecha de publicación:2018
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/344501
Acceso en línea:http://hdl.handle.net/10261/344501
https://api.elsevier.com/content/abstract/scopus_id/85053672193
Access Level:acceso abierto
Palabra clave:Boron
Carboranes
Cross-coupling
Imaging agents
Photoluminescent material
Descripción
Sumario:A small library of carborane-BODIPY/aza-BODIPY dyads were efficiently synthesized by means of a novel convergent synthetic approach, the key step of which is a Pd-catalyzed Heck coupling reaction. The structural characterization and photoluminescence properties of the newly synthesized dyads were evaluated. The presence of the carborane did not significantly alter the photophysical patterns of the BODIPY or aza-BODIPY in the final fluorophores, but it produced a decrease of the emission fluorescent quantum yields that was in the range from 1.4 % for aza-BODIPY to 48 % for BODIPY-dyads. The carborane-BODIPY dyads were successfully incorporated into cells, especially compounds 2, 4 and 13, demonstrating their cytoplasmic localization. The fluorescent and biocompatibility properties make these compounds good candidates for in vitro cell tracking.