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Two‐Photon Absorption and Cell Imaging of Fluorene‐Functionalized Epicocconone Analogues
Author(s) -
Oger Samuel,
Schapman Damien,
Mougeot Romain,
Leleu Stéphane,
Lascoux Noëlle,
Baldeck Patrice,
Bénard Magalie,
Gallavardin Thibault,
Galas Ludovic,
Franck Xavier
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201902731
Subject(s) - fluorophore , fluorescence , chromophore , absorption (acoustics) , fluorene , natural product , photochemistry , fluorescence microscope , chemistry , oxazines , two photon absorption , materials science , stereochemistry , organic chemistry , optics , physics , composite material , polymer , laser
Epicocconone 1 is a natural chromophore isolated from the fungus Epicoccum nigrum that has shown applications in proteomics and fluorescent microscopy thanks to its unique pro‐fluorescence properties. The modification of the skeleton of the natural product by replacing the triene side chain by a fluorenyl scaffold can noticeably increase the fluorophore's absorption coefficient. The synthesis of the analogues of the natural product has been made possible by the use of a palladium‐catalyzed carbonylation reaction, allowing the construction of the β‐keto‐dioxinone key intermediate. Two‐photon absorption cross‐section measurements of the fluorenyl epicocconone analogues show a structure dependency with values ranging from 60 to 280 GM and live cell imaging show intense staining of intracellular vesicle‐like structures around the nucleus.