An expedient synthesis of N,N-dialkylamino-dihydroxanthene-pyrylium conjugated near-infrared fluorescent dyes
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Titre | An expedient synthesis of N,N-dialkylamino-dihydroxanthene-pyrylium conjugated near-infrared fluorescent dyes |
Type de publication | Journal Article |
Year of Publication | 2016 |
Auteurs | Romieu A, Richard J-A |
Journal | TETRAHEDRON LETTERS |
Volume | 57 |
Pagination | 317-320 |
Date Published | JAN 20 |
Type of Article | Article |
ISSN | 0040-4039 |
Mots-clés | Cascade reactions, NIR dyes (Nor)dihydroxanthenes, Pyrylium dyes |
Résumé | 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 pi-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. (C) 2015 Elsevier Ltd. All rights reserved. |
DOI | 10.1016/j.tetlet.2015.12.010 |