3 years ago

N-Bridged Annulated BODIPYs: Synthesis of Highly Fluorescent Blueshifted Dyes

N-Bridged Annulated BODIPYs: Synthesis of Highly Fluorescent Blueshifted Dyes
Hua Lu, Zhifang Li, Yanping Wu, Xuqiong Xiao, Zhen Shen, John Mack
A series of novel BODIPY dyes has been prepared through the introduction of an N-bridged annulated meso-phenyl ring at one of the β-positions of the BODIPY core. An unusual blueshift of the main spectral bands is observed, since the fusion of a meso-substituent results in a marked relative destabilization of the LUMO. The greater rigidity of the ring-fused structure leads to very high fluorescence quantum yields. The position of the main spectral bands can be fine-tuned by introducing electron withdrawing and donating groups onto the meso-phenyl ring. Bright and blue: A series of novel meso, β-annulated N-bridged boron dipyrromethene (BODIPY) dyes were designed, which exhibit an unusual blueshift of the main spectral bands with very high fluorescence quantum yields.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/asia.201700584

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