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A General Strategy for Development of Near‐Infrared Fluorescent Probes for Bioimaging
Author(s) -
Chen Wei,
Xu Shi,
Day Jacob J.,
Wang Difei,
Xian Ming
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201710688
Subject(s) - fluorescence , fluorophore , near infrared spectroscopy , aqueous solution , chemistry , nanotechnology , stokes shift , photochemistry , materials science , organic chemistry , optics , physics
Near‐infrared (NIR) fluorescent dyes with favorable photophysical properties are highly useful for bioimaging, but such dyes are still rare. The development of a unique class of NIR dyes via modifying the rhodol scaffold with fused tetrahydroquinoxaline rings is described. These new dyes showed large Stokes shifts (>110 nm). Among them, WR3, WR4, WR5, and WR6 displayed high fluorescence quantum yields and excellent photostability in aqueous solutions. Moreover, their fluorescence properties were tunable by easy modifications on the phenolic hydroxy group. Based on WR6, two NIR fluorescent turn‐on probes, WSP‐NIR and SeSP‐NIR, were devised for the detection of H 2 S. The probe SeSP‐NIR was applied in visualizing intracellular H 2 S. These dyes are expected to be useful fluorophore scaffolds in the development of new NIR probes for bioimaging.