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

• Published in: Chemistry : a European journal 2023-06, Vol.29 (35)
• Main Authors: Miao, Wei, Gan, Rui, Liu, Wanxiao, Guo, Xing, Wu, Qinghua, Wei, Ying, Yu, Changjiang, Hao, Erhong, Jiao, Lijuan
• Format: Article
• Language: English
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.202300449

Aromatic 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 of α , 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 of 3 a was red‐shifted by 53 nm to 693 nm after forming aggregates.