DOI: 10.1002/asia.202300852 ISSN: 1861-4728

3‐halochromones through oxidative α‐halogenation of enaminones and photophysical investigation: another case of photo‐induced partially aromatized intramolecular charge transfer?

José Sebastião Santos Neto, Filipe Teodoro Coelho, Carlos Vinícius Doerner, Antonio Luiz Braga, Luciano Morais Liao, Felipe Lange Coelho
  • General Chemistry
  • Biochemistry
  • Organic Chemistry

A versatile synthesis strategy for fluorescent 3‐halo‐4H‐chromen‐4‐one derivatives is reported. The method involves the oxidative α‐halogenation of enaminones performed by an efficient and sustainable oxidation system. The use of Oxone in combination with KCl, KBr, or KI enables the preparation of 3‐chloro‐, 3‐bromo‐, or 3‐iodo‐4H‐chromen‐4‐one in good to excellent yields, with great functional group tolerance where the protocol is amenable to gram‐scale synthesis. The analysis of the photophysical properties of the presented 4H‐chromen‐4‐one showed absorption in the UV region and fluorescence emission in the violet‐to‐cyan region with a relatively large Stokes shift. In solution, all compounds present a dual fluorescence emission, regardless of the solvent, assigned to a partially aromatised intramolecular charge transfer mechanism, considering the presence of a pseudo‐aromatic ring in the chromone scaffold and the absence of the influence of substituent electronic features in optical behaviour.

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