Year: 2024
Type: article
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.
Source: Chemistry - A European Journal
Institution: University of Copenhagen
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
OpenAlex ID: W4404072837