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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Veröffentlicht in: | Chemistry : a European journal 2024-11, p.e202403451 |
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Hauptverfasser: | , , , , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | 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. |
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ISSN: | 0947-6539 1521-3765 1521-3765 |
DOI: | 10.1002/chem.202403451 |