Acid-Catalyzed Dehydrative Nucleophilic Substitutions of 2,6-Di(hydroxymethyl) BODIPYs: A Platform for BODIPY Functionalization
We report the synthesis of the novel 2,6-di(hydroxymethyl)-1,3,5,7-tetramethyl-8-phenyl BODIPY and its utility in efficient Lewis-acid-catalyzed dehydrative nucleophilic substitution reactions. This diol, readily prepared via a formylation/reduction sequence from the corresponding tetramethyl BODIPY, undergoes bisfunctionalization with a variety of nucleophiles to yield 2,6-substituted BODIPY fluorophores. Notably, the use of trimethylsilyl azide as a nucleophile provides a "clickable" BODIPY, suited for bioconjugation. Furthermore, employing BODIPY or BOPHY as a nucleophile successfully led to a BODIPY trimer and the first example of bis(BOPHY)-BODIPY, respectively, with the latter showcasing its potential as a novel light-harvesting fluorophore.
Authors
- Jorge Bañuelos (ORCID: https://orcid.org/0000-0002-8444-4383)
- Natalia Casado (ORCID: https://orcid.org/0000-0003-4705-2679)
- J. Cristobal López (ORCID: https://orcid.org/0000-0003-0370-4727)
- Clara Uriel (ORCID: https://orcid.org/0000-0003-4598-7438)
- Lourdes Infantes (ORCID: https://orcid.org/0000-0001-6932-4212)
- Eduardo Duque-Redondo (ORCID: https://orcid.org/0000-0002-1890-4687)
- Inmaculada García‐Moreno (ORCID: https://orcid.org/0000-0002-8682-3715)
- Ana M. Gómez (ORCID: https://orcid.org/0000-0002-8703-3360)
- Alberto Hernández
Institutions
- Consejo Superior de Investigaciones Científicas (ES)
- University of the Basque Country (ES)
- Instituto de Física Fundamental (ES)
- Instituto de Química Física Blas Cabrera (ES)
- Instituto de Química Orgánica General (ES)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-12-08
- DOI
- https://doi.org/10.1021/acs.orglett.5c04625
- Primary Topic
- Luminescence and Fluorescent Materials
- Type
- article
- Field-Weighted Citation Impact
- 0.00