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Article Dans Une Revue Organic & Biomolecular Chemistry Année : 2019

Divergent synthesis of 5 `,7 `-difluorinated dihydroxanthene-hemicyanine fused near-infrared fluorophores

Résumé

We describe an expedient access to a 5', 6', 7'-trifluoro dihydroxanthene-hemicyanine fused scaffold in 2 steps and 54% overall yield from the corresponding salicylic aldehyde. A 6'-regioselective nucleophilic aromatic substitution (SNAr) reaction with a wide range of nitrogen, sulfur or selenium nucleophiles then gives access to 16 near-infrared (NIR) fluorophores emitting in the 710-750 nm range. We also report the experimental and theoretical photophysical investigations of these unique optical agents that include the first series of 6'-heavy atom substituted dihydroxanthenes, extending the pool of polyfluorinated markers for biomedical and material applications.

Domaines

Chimie
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Dates et versions

hal-02140853 , version 1 (30-12-2021)

Identifiants

Citer

Shasha Zheng, Gu Lingyue, Michelle Jui Hsien Ong, Denis Jacquemin, Anthony Romieu, et al.. Divergent synthesis of 5 `,7 `-difluorinated dihydroxanthene-hemicyanine fused near-infrared fluorophores. Organic & Biomolecular Chemistry, 2019, 17 (17), pp.4291-4300. ⟨10.1039/c9ob00568d⟩. ⟨hal-02140853⟩
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