Tuning Tetramethoxy-acridiniums for Fluorophores and Organic Photoredox Catalysis

Tetramethoxy substituted alkyl-acridiniums (TMAcr ) are readily available by facile nucleophilic aromatic substitution on tris(2,6-dimethoxyphenyl)carbenium, but are non-fluorescent, presumably due to intramolecular photoinduced electron transfer quenching. In this work we introduce electron withdra...

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Bibliographic Details
Published in:Chemistry : a European journal 2024-11, p.e202403451
Main Authors: Nowack, Marko H, Johansen, Magnus B, Sams, Søren, Hillers-Bendtsen, Andreas E, Mikkelsen, Kurt V, Laursen, Bo W
Format: Article
Language:English
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Summary:Tetramethoxy substituted alkyl-acridiniums (TMAcr ) are readily available by facile nucleophilic aromatic substitution on tris(2,6-dimethoxyphenyl)carbenium, but are non-fluorescent, presumably due to intramolecular photoinduced electron transfer quenching. In this work we introduce electron withdrawing groups by electrophilic aromatic substitution reactions, leading to fluorescence turn-on. The acridiniums are moderately fluorescent (φ =20 %) with long fluorescene lifetimes (τ =9 ns). The positive excited state reduction potentials (E* =+1.6 V) make the TMAcr excellent electron acceptors in the excited state, and efficient reductive photoredox catalysts able to oxidize a broad range of substrates.
ISSN:0947-6539
1521-3765
1521-3765
DOI:10.1002/chem.202403451