4.7 Article

FormylBODIPYs: Privileged Building Blocks for Multicomponent Reactions. The Case of the Passerini Reaction

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 7, Pages 2888-2898

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b02893

Keywords

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Funding

  1. MINECO [MAT2014-51937-C3-03]
  2. Gobierno Vasco of Spain [IT339-10, IT912-16]
  3. CONACyT [129572, 123732, CB2011-166860, PN2014-247109]
  4. Universidad de Guanajuato [DAIP-529/2015]

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Eleven formyl-containing BODIPY dyes were prepared by means of either the Liebeskind-Srogl cross-coupling reaction or the Vilsmeier reaction. These dyes were used as components in the Passerini reaction to give highly substituted BODIPY dyes. A joined spectroscopic and theoretical characterization of the synthesized compounds was conducted to unravel the impact of the structural rigidity/flexibility on the photophysical signatures. These dyes were tested as fluorescent trackers for phagocytosis. Additionally, they proved to be useful to stain different blood cells with an intense and stable signal at a very low exposure time.

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