Design, synthesis, and time-gated cell imaging of carbon-bridged triangulenium dyes with long fluorescence lifetime and red emission

Chemical Science
M RosenbergBo W Laursen

Abstract

Time-resolved fluorescence offers many advantages over normal steady-state detection and becomes increasingly important in bioimaging. However, only very few fluorophores with emission in the visible range and fluorescence lifetimes above 5 ns are available. In this work, we prepare a series of new aza/oxa-triangulenium dyes where one of the usual oxa or aza bridges is replaced by an isopropyl bridge. This leads to a significant redshift of fluorescence with only moderate reductions of quantum yields and a unique long fluorescence lifetime. The fluorescence of the isopropyl bridged diazatriangulenium derivative CDATA+ is red-shifted by 50 nm (1400 cm-1) as compared to the oxygen-bridged DAOTA+ chromophore and has intense emission in the red region (600-700 nm) with a quantum yield of 61%, and a fluorescence lifetime of 15.8 ns in apolar solution. When the CDATA+ dye is used as cell stain, high photostability and efficient time-gated cell imaging is demonstrated.

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Citations

Apr 27, 2018·Chemistry : a European Journal·Irene Hernández DelgadoJérôme Lacour
May 21, 2019·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Mette L H SørensenThorsten Hansen
Oct 4, 2019·Beilstein Journal of Organic Chemistry·Marco SantellaBo W Laursen
Jun 10, 2020·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Shivesh SabbarwalManoj Kumar
Jan 12, 2021·Journal of the American Chemical Society·Laura KacenauskaiteBo W Laursen
Mar 23, 2021·Angewandte Chemie·Hajime GotohTakuji Hatakeyama
Sep 11, 2020·The Journal of Organic Chemistry·Maya MarinovaJérôme Lacour
Jan 30, 2019·The Journal of Organic Chemistry·Martin RosenbergBo W Laursen
Nov 19, 2021·The Journal of Organic Chemistry·Jesper Dahl JensenBo W Laursen

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Methods Mentioned

BETA
super-resolution microscopy
column chromatography
X-ray
confocal microscopy
Fluorescence
fluorescence microscopy
fluorescence imaging

Software Mentioned

DMQA
DAOTA

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