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

Chiara Bellomo, Mahdi Chaari, Justo Cabrera-González, Marco Blangetti, Chiara Lombardi, Annamaria Deagostino, Clara Viñas, Nerea Gaztelumendi, Carme Nogués, Rosario Nuñez, Cristina Prandi

Research output: Contribution to journalArticleResearch

9 Citations (Scopus)

Abstract

© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 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.
Original languageEnglish
Pages (from-to)15622-15630
JournalChemistry - A European Journal
Volume24
DOIs
Publication statusPublished - 17 Oct 2018

Keywords

  • boron
  • carboranes
  • cross-coupling
  • imaging agents
  • photoluminescent material

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