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Synthesis of Near-Infrared Fluorescent Two-Photon-Absorbing Fluorenyl Benzothiadiazole and Benzoselenadiazole Derivatives

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journal contribution
posted on 07.12.2016, 13:22 by Sheng Yao, Bosung Kim, Xiling Yue, Maria Y. Colon Gomez, Mykhailo V. Bondar, Kevin D. Belfield
A series of dyes 25 based on 5-thienyl-2,1,3-benzothiadiazole and 5-thienyl-2,1,3-benzoselenadiazole cores were synthesized as near-infrared-emitting two-photon-absorbing fluorophores. Fluorescence maxima wavelengths as long as 714 nm and quantum yields as high as 0.67 were realized. The fluorescence quantum yields of dyes 24 were nearly constant, regardless of solvent polarity. These diazoles exhibited large Stokes shifts (>110 nm) and high two-photon figure of merit. Cells incubated on a 3D scaffold with probe 4 (encapsulated in Pluronic micelles) exhibited bright fluorescence, enabling 3D two-photon fluorescence imaging to a depth of 100 μm.