Synthesis of Near-Infrared Fluorescent Two-Photon-Absorbing Fluorenyl Benzothiadiazole and Benzoselenadiazole Derivatives
journal contributionposted 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 2–5 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 2–4 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.
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thienyltwo-photon figure3 D two-photon fluorescence imagingBenzoselenadiazole Derivativesquantum yieldsprobe 4100 μ mnear-infrared-emitting two-photon-absorbing fluorophoresdye3 D scaffoldPluronic micellesTwo-Photon-Absorbing Fluorenyl Benzothiadiazole5-fluorescence quantum yields714 nmFluorescence maxima wavelengths