3‐Halochromones Through Oxidative α‐Halogenation of Enaminones and its Photophysical Investigation: Another Case of Photo‐induced Partially Aromatised Intramolecular Charge Transfer?

Author:

Neto José S. S.1ORCID,Coelho Filipe T.1ORCID,Doerner Carlos V.2,Braga Antonio L.2ORCID,Lião Luciano M.1,Coelho Felipe L.1

Affiliation:

1. Universidade Federal de Goiás 74690-900 Goiânia GO Brazil

2. Departamento de Química Universidade Federal de Santa Catarina 88040-970 Florianópolis SC Brazil

Abstract

AbstractA 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.

Funder

Conselho Nacional de Desenvolvimento Científico e Tecnológico

Fundação de Amparo à Pesquisa do Estado de Goiás

Fundação de Apoio à Pesquisa, Universidade Federal de Goiás

Publisher

Wiley

Subject

General Chemistry,Biochemistry,Organic Chemistry

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