Photostable π-Expanded Furans via Base-Mediated Quinone Oxygen-Annulation
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.
Fields of Study & Subjects
Synthesis and Properties of Aromatic Compounds
Organic Electronics and Photovoltaics
Photochromic and Fluorescence Chemistry
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 7
- Pages
- 2837–2843
- Publication date
- 10 February 2026
- Language
- EN