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Novel Method for the Synthesis of Merocyanines: New Photophysical Possibilities for a Known Class of Fluorophores

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dc.abstract.enA new, transformative method for the preparation of rhodols and other merocyanines from readily available tetrafluorohydroxybenzaldehyde and aminophenols has been developed. It is now possible to prepare merocyanines bearing three fluorine atoms and additional conjugated rings, and the whole one-pot process occurs under neutral, mild conditions. Three heretofore unknown merocyanine-based architectures were prepared using this strategy from aminonaphthols and 4-hydroxycoumarins. The ability to change the structure of original rhodol chromophore into π-expanded merocyanines translates to a comprehensive method for the modulation of photophysical properties, such as shifting the absorption and emission bands across almost the entire visible spectrum, reaching a huge Stokes shift i. e. 4800 cm−1, brightness approximately 80.000 M−1 cm−1, two-photon absorption cross-section above 150 GM and switching-on/off solvatofluorochromism. A detailed investigation allowed to rationalize the different spectroscopic behavior of rhodols and new merocyanines, addressing solvatochromism and two-photon absorption.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorDobrzycki, Łukasz
dc.contributor.authorPainelli, Anna
dc.contributor.authorTerenziani, Francesca
dc.contributor.authorGryko, Daniel
dc.contributor.authorVAKULIUK, OLENA
dc.contributor.authorKOSZARNA, Beata
dc.contributor.authorVygranenko, Kateryna
dc.contributor.authorBardi, Brunella
dc.date.accessioned2024-01-25T13:52:25Z
dc.date.available2024-01-25T13:52:25Z
dc.date.copyright2023-05-19
dc.date.issued2023
dc.description.accesstimeAT_PUBLICATION
dc.description.financeNie dotyczy
dc.description.number45
dc.description.versionFINAL_PUBLISHED
dc.description.volume29
dc.identifier.doi10.1002/CHEM.202300979
dc.identifier.issn0947-6539
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/113958
dc.identifier.weblinkhttp://dx.doi.org/10.1002/chem.202300979
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofChemistry - A European Journal
dc.relation.pagese202300979
dc.rightsCC-BY-NC-ND
dc.sciencecloudnosend
dc.titleNovel Method for the Synthesis of Merocyanines: New Photophysical Possibilities for a Known Class of Fluorophores
dc.typeJournalArticle
dspace.entity.typePublication