Benzene-fused bis(acenaphthoBODIPY)s, stable near-infrared-selective dyes

Uno, Hidemitsu; Honda, Takayuki; Kitatsuka, Manami; Hiraoka, Shogo; Mori, Shigeki; Takase, Masayoshi; Okujima, Tetsuo; Nakae, Takahiro

doi:10.1039/c8ra01694a

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Cited by 8 publications

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

Miao

Gan

Liu

et al. 2023

Chemistry A European J

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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.

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