Diarenofuran[]-fused BODIPYs: One-Pot SAr-Suzuki Synthesis and Properties.

We present a streamlined methodology that integrates regioselective tetrahalogen-BODIPY and -hydroxyphenylboronic acid in a one-pot process, leveraging SAr nucleophilic substitution in conjunction with Suzuki coupling to afford diarenofuran []-fused BODIPYs (-) with commendable yields (85-95%) and short reaction times (0.5-1.0 h). X-ray structure analyses of , elucidate that these diarenofuran[]-fused BODIPYs adopt a "butterfly" conformation, maintaining a highly rigid planarity. A comprehensive examination of the spectroscopic and electrochemical properties of these diarenofuran[]-fused BODIPY derivatives, incorporating various substituents, reveals intriguing characteristics, including pronounced absorption and emission in the near-infrared region (NIR), elevated fluorescence quantum yields (Φ = 75-89% in dichloromethane), and tunable HOMO-LUMO levels. Remarkably, compared to -, possesses a large extended π-conjugated system, resulting in significant red shifts in its absorption and emission maxima, reaching 623 and 635 nm, respectively, and a reduced HOMO-LUMO gap. Despite this substantial structural expansion, maintains a surprisingly high fluorescence quantum yield (Φ = 80%), underscoring its exceptional photophysical performance and strong potential for applications requiring efficient NIR emission and robust fluorescence retention.