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Issue 12, 2018
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Design, synthesis, and time-gated cell imaging of carbon-bridged triangulenium dyes with long fluorescence lifetime and red emission

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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.

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

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Supplementary files

Article information


Submitted
08 Jan 2018
Accepted
15 Feb 2018
First published
23 Feb 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 3122-3130
Article type
Edge Article

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

M. Rosenberg, K. R. Rostgaard, Z. Liao, A. Ø. Madsen, K. L. Martinez, T. Vosch and B. W. Laursen, Chem. Sci., 2018, 9, 3122
DOI: 10.1039/C8SC00089A

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