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Acid-Catalyzed Dehydrative Nucleophilic Substitutions of 2,6-Di(hydroxymethyl) BODIPYs: A Platform for BODIPY
Clara Uriel1, Alberto Hernández1, Natalia Casado2
1Instituto de Química Orgánica General (IQOG), Consejo Superior de Investigaciones Científicas (CSIC), Juan de la Cierva 3, 28006 Madrid, Spain.
Abstract:
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.
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