An expedient synthesis of N,N-dialkylamino-dihydroxanthene-pyrylium conjugated near-infrared fluorescent dyes

Abstract : An expedient synthesis of amino-(nor)dihydroxanthene-based fluorophores is reported, proceeding in two steps from commercially available salicylic aldehydes. The synthesis relies on the one-pot construction of the (nor)dihydroxanthene scaffolds through an oxa-Michael/retro-Michael/vinylogous aldol/dehydration cascade sequence. Further extension of the π-conjugated systems through a condensation reaction with a 2,4,6-trisubstituted pyrylium salt led to a novel class of near-infrared (NIR) fluorescent dyes with absorption/emission maxima in polar media in the ranges of 705–778 and 785–828 nm, respectively.
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https://hal-univ-bourgogne.archives-ouvertes.fr/hal-01391818
Contributeur : Icmub - Université de Bourgogne <>
Soumis le : jeudi 3 novembre 2016 - 19:30:45
Dernière modification le : jeudi 4 avril 2019 - 10:18:05

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Anthony Romieu, Jean-Alexandre Richard. An expedient synthesis of N,N-dialkylamino-dihydroxanthene-pyrylium conjugated near-infrared fluorescent dyes. Tetrahedron Letters, Elsevier, 2016, 57 (3), pp.317 - 320. ⟨http://www.sciencedirect.com/science/article/pii/S0040403915304251⟩. ⟨10.1016/j.tetlet.2015.12.010⟩. ⟨hal-01391818⟩

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