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Chemoselective Alteration of Fluorophore Scaffolds as a Strategy for the Development of Ratiometric Chemodosimeters
Author(s) -
Zhou Xinqi,
Lesiak Lauren,
Lai Rui,
Beck Jon R.,
Zhao Jia,
Elowsky Christian G.,
Li Hui,
Stains Cliff I.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201612628
Subject(s) - fluorophore , xanthene , fluorescence , chemistry , photochemistry , bodipy , near infrared spectroscopy , combinatorial chemistry , nanotechnology , materials science , optics , physics
Ratiometric sensors generally couple binding events or chemical reactions at a distal site to changes in the fluorescence of a core fluorophore scaffold. However, such approaches are often hindered by spectral overlap of the product and reactant species. We provide a strategy to design ratiometric sensors that display dramatic spectral shifts by leveraging the chemoselective reactivity of novel functional groups inserted within fluorophore scaffolds. As a proof‐of‐principle, fluorophores containing a borinate ( RF 620 ) or silanediol ( SiOH2R ) functionality at the bridging position of the xanthene ring system are developed as endogenous H 2 O 2 sensors. Both these fluorophores display far‐red to near‐infrared excitation and emission prior to reaction. Upon oxidation by H 2 O 2 both sensors are chemically converted to tetramethylrhodamine, producing significant (≥66 nm) blue‐shifts in excitation and emission maxima. This work provides a new concept for the development of ratiometric probes.