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

ABSTRACT: 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 ?m.

SUBMITTER: Yao S

PROVIDER: S-EPMC6640770 | biostudies-literature | 2016 Dec

REPOSITORIES: biostudies-literature

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

Yao Sheng S Kim Bosung B Yue Xiling X Colon Gomez Maria Y MY Bondar Mykhailo V MV Belfield Kevin D KD

ACS omega 20161207 6

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 mer ...[more]

PMID: 31457186

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