Year: 2026
Type: preprint
Abstract: The adoption of photocatalytic approaches for utilising small organic molecules in self‑catalysed reactions offers opportunities in green organic synthesis. We report that alkylated boron‑dipyrromethenes (BODIPYs) act as self‑photoredox catalysts for their own oxidation under mild visible‑light conditions. Using an imidazolinium salt (NHC-H) as a quencher, alkylated BODIPYs are oxidised cleanly to the corresponding hydroxymethyl derivatives in a one‑pot process. Luminescence studies, including Stern–Volmer analysis, support a reductive‑quenching pathway in which the NHC-H transfers an electron to photoexcited BODIPY to give a BODIPY radical anion. The method proceeds without external photocatalysts or stoichiometric oxidants and shows good functional‑group tolerance, highlighting the potential of these chromophores both as substrates and catalytic light absorbers. Moreover, the synthesized molecules were demonstrated to behave as effective passivating agents for layered Mn2+
Source: ChemRxiv
Institution: Khalifa University of Science and Technology
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W7221100837