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Synthesis of a Far‐Red Photoactivatable Silicon‐Containing Rhodamine for Super‐Resolution Microscopy
Author(s) -
Grimm Jonathan B.,
Klein Teresa,
Kopek Benjamin G.,
Shtengel Gleb,
Hess Harald F.,
Sauer Markus,
Lavis Luke D.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201509649
Subject(s) - xanthene , fluorophore , rhodamine , fluorescence , chemistry , moiety , photochemistry , molecule , microscopy , rhodamine b , stereochemistry , organic chemistry , optics , physics , photocatalysis , catalysis
The rhodamine system is a flexible framework for building small‐molecule fluorescent probes. Changing N ‐substitution patterns and replacing the xanthene oxygen with a dimethylsilicon moiety can shift the absorption and fluorescence emission maxima of rhodamine dyes to longer wavelengths. Acylation of the rhodamine nitrogen atoms forces the molecule to adopt a nonfluorescent lactone form, providing a convenient method to make fluorogenic compounds. Herein, we take advantage of all of these structural manipulations and describe a novel photoactivatable fluorophore based on a Si‐containing analogue of Q‐rhodamine. This probe is the first example of a “caged” Si‐rhodamine, exhibits higher photon counts compared to established localization microscopy dyes, and is sufficiently red‐shifted to allow multicolor imaging. The dye is a useful label for super‐resolution imaging and constitutes a new scaffold for far‐red fluorogenic molecules.