ArticleOrganic letters2025
Acid-Catalyzed Dehydrative Nucleophilic Substitutions of 2,6-Di(hydroxymethyl) BODIPYs: A Platform for BODIPY Functionalization.
Article in Organic letters, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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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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