Tuning Tetramethoxy-acridiniums for Fluorophores and Organic Photoredox Catalysis

Marko H. Nowack, Magnus B. Johansen, Søren Sams, Andreas E. Hillers-Bendtsen, Kurt V. Mikkelsen, Bo W. Laursen*

*Corresponding author af dette arbejde

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Abstract

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 (φf=20 %) with long fluorescene lifetimes (τf=9 ns). The positive excited state reduction potentials (E*red=+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.

OriginalsprogEngelsk
TidsskriftChemistry - A European Journal
Vol/bind31
Udgave nummer4
ISSN0947-6539
DOI
StatusUdgivet - 2024

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