Issue 20, 2022

Silicon functionalization expands the repertoire of Si-rhodamine fluorescent probes

Abstract

Fluorescent dyes such as rhodamines are widely used to assay the activity and image the location of otherwise invisible molecules. Si-rhodamines, in which the bridging oxygen of rhodamines is replaced with a dimethyl silyl group, are increasingly the dye scaffold of choice for biological applications, as fluorescence is shifted into the near-infrared while maintaining high brightness. Despite intense interest in Si-rhodamines, there has been no exploration of the scope of silicon functionalization in these dyes, a potential site of modification that does not exist in conventional rhodamines. Here we report a broad range of silyl modifications that enable brighter dyes, further red-shifting, new ways to modulate fluorescence, and the introduction of handles for dye attachment, including fluorogenic labeling agents for nuclear DNA, SNAP-tag and HaloTag labeling. Modifications to the bridging silicon are therefore of broad utility to improve and expand the applications of all Si-dyes.

Graphical abstract: Silicon functionalization expands the repertoire of Si-rhodamine fluorescent probes

Supplementary files

Article information

Article type
Edge Article
Submitted
29 mar 2022
Accepted
30 apr 2022
First published
02 may 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2022,13, 6081-6088

Silicon functionalization expands the repertoire of Si-rhodamine fluorescent probes

D. N. Rao, X. Ji and S. C. Miller, Chem. Sci., 2022, 13, 6081 DOI: 10.1039/D2SC01821G

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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