Light-Induced, Iron-Promoted Formation of Benzotetraphenones via Paternò–Büchi Photorearrangement/Electrocyclization: A Route to Polyaromatic Scaffolds
Abstract We report a light-induced, iron-promoted method for the synthesis of polyaromatic benzotetraphenone derivatives via a tandem [2+2] Paternò–Büchi photorearrangement/electrocyclization pathway. Irradiation of anthraquinone with diphenylacetylenes under 370 nm LED light in the presence of FeCl₃ afforded novel polyaromatic scaffolds in excellent yields. The structures of the products were confirmed by single-crystal X-ray diffraction, revealing planar, rigid frameworks with promising photophysical properties. This strategy offers a new platform for constructing highly conjugated, luminescent molecules from simple precursors under mild conditions.
Authors
- Luana A. Machado (ORCID: https://orcid.org/0000-0003-3542-915X)
- Maria H. Araújo (ORCID: https://orcid.org/0000-0002-2609-0281)
- Willian X. C. Oliveira (ORCID: https://orcid.org/0000-0003-0722-5352)
- Renata G. Almeida (ORCID: https://orcid.org/0000-0003-2896-0487)
- Guilherme A. M. Jardim (ORCID: https://orcid.org/0000-0002-9882-3085)
- Ícaro A. O. Bozzi (ORCID: https://orcid.org/0000-0002-0696-0833)
- Eufrânio N. da Silva Júnior (ORCID: https://orcid.org/0000-0003-1281-5453)
- Edmond Gravel (ORCID: https://orcid.org/0000-0001-6077-1016)
- Bruno Dival
- Dandara dos Santos Borges
Institutions
- Universidade Federal de Minas Gerais (BR)
- Commissariat à l'Énergie Atomique et aux Énergies Alternatives (FR)
- Institut des Sciences du Vivant Frédéric Joliot (FR)
Publication Details
- Journal
- Synlett
- Published
- 2025-09-19
- DOI
- https://doi.org/10.1055/a-2705-9158
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00