ArticleThe Journal of organic chemistry2026
Photostable π-Expanded Furans via Base-Mediated Quinone Oxygen-Annulation.
Article in The Journal of organic chemistry, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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4 authors.
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Abstract
A one-pot oxygen-annulation couples chloroquinones with aromatic alcohols to efficiently construct π-expanded furans in yields up to 91%. Subsequent TIPS-acetylene functionalization and reductive aromatization enhance solubility and furnish bench-stable chromophores that absorb in the blue and exhibit strong fluorescence. Time-dependent density functional theory (TD-DFT) reveals low-energy, charge-transfer excitations in the quinone intermediates, which shift to higher-energy, localized π-π* transitions upon aromatization. Remarkably, these π-expanded furans withstand UV irradiation over 10-fold longer than TIPS-pentacene, highlighting their exceptional photostability.
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