Carborane‐BODIPY Dyads: New Photoluminescent Materials through an Efficient Heck Coupling. Issue 58 (19th September 2018)

• Record Type: Journal Article
• Authors: Bellomo, Chiara; Chaari, Mahdi; Cabrera‐González, Justo; Blangetti, Marco; Lombardi, Chiara; Deagostino, Annamaria; Viñas, Clara; Gaztelumendi, Nerea; Nogués, Carme; Nuñez, Rosario; Prandi, Cristina
• Is Part Of: Chemistry. Volume 24:Issue 58(2018)
• Page Start: 15622
• Page End: 15630
• Publication Date: 2018-09-19
• Subjects: imaging agents -- boron -- carboranes -- cross-coupling -- photoluminescent material; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201802901
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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 compounds2, 4 and13, demonstrating their cytoplasmic localization. The fluorescent and biocompatibility properties make these compounds good candidates for in vitro cell tracking. Abstract : The efficient Pd‐catalyzed Heck coupling reaction between BODIPY, aza‐DIPYs and styrenyl carboranes leads to a small library of carborane‐BODIPY/aza‐BODIPY dyads. Their fluorescence properties and internalization by HeLa cells make these compounds good candidates for in vitro cell tracking.