Palladium Catalyzed, Annulative Multiple C‐H Bond Activations of BODIPYs to Access π‐Extended Polycyclic Heteroaromatic Molecules with Deep Red Emissions andSelf‐aggregation Behaviors

Abstract

AbstractAromatic ring fusion on BODIPY core can effectively tune its electronic property, and red‐shift its absorption and emission wavelength. In this work, we report that a one‐pot Pd(II) catalyzed multiple C−H activation to access acenaphtho[b]‐fused BODIPYs though the reaction ofα,β‐unsubstituted‐BODIPYs and 1,8‐dibromonaphthalenes. These newly synthesized acenaphtho[b]‐fused BODIPYs revealed intensified deep red absorptions (639–669 nm) and emissions (643–683 nm), with high fluorescence quantum yields (0.53–0.84) in dichloromethane. Notably, these acenaphtho[b]‐fused BODIPYs exhibited well‐defined self‐aggregation behavior in water/THF mixture, and for instance, the absorption of3 awas red‐shifted by 53 nm to 693 nm after forming aggregates.