Alkyl-BODIPYs as a Self-Photoredox Catalyst for their Oxidative Hydroxymethylation
- 1Department of Chemistry, Khalifa University, SAN Campus, Abu Dhabi, UAE
- 2Chemical Crystallography Laboratory
- 3Khalifa University of Science and Technology
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+
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BibTeX
@misc{sultan2026alkylbodipys,
title = {{Alkyl-BODIPYs as a Self-Photoredox Catalyst for their Oxidative Hydroxymethylation}},
author = {Shaista Sultan and Praveen B. Managutti and Ahmed Abdelhady and Ramon Rios},
howpublished = {ChemRxiv},
year = {2026},
month = oct,
doi = {10.26434/chemrxiv.15010141/v1},
url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010141/v1},
note = {CC BY},
}
RIS
TY - UNPB
TI - Alkyl-BODIPYs as a Self-Photoredox Catalyst for their Oxidative Hydroxymethylation
AU - Shaista Sultan
AU - Praveen B. Managutti
AU - Ahmed Abdelhady
AU - Ramon Rios
PY - 2026
DA - 2026/10/09
PB - ChemRxiv
DO - 10.26434/chemrxiv.15010141/v1
UR - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010141/v1
AB - 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+
ER -