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Issue 23, 2014
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Switchable fluorescence by click reaction of a novel azidocarbazole dye

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Abstract

Imaging is – even these days – still restricted to of a few classes of robust dyes. A demand for switchable tags led us to the design of a new class of pre-fluorophores. We achieved this by using a non-fluorescent N-(4-azidophenyl)-carbazole tag which turns fluorescent by click reaction with alkynes and cyclooctynes. The spectral properties of the labelled dyes were investigated. Our results suggest that a twisted internal charge transfer (TICT) transition is responsible for the emission. DFT calculations and single-crystal X-ray diffraction of selected examples support this explanation. The feasibility of the new dyes for biological application has also been tested via confocal microscopy.

Graphical abstract: Switchable fluorescence by click reaction of a novel azidocarbazole dye

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Publication details

The article was received on 25 Dec 2013, accepted on 31 Jan 2014 and first published on 06 Feb 2014


Article type: Paper
DOI: 10.1039/C3RA47964A
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RSC Adv., 2014,4, 11528-11534
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    Switchable fluorescence by click reaction of a novel azidocarbazole dye

    A. Hörner, D. Volz, T. Hagendorn, D. Fürniss, L. Greb, F. Rönicke, M. Nieger, U. Schepers and S. Bräse, RSC Adv., 2014, 4, 11528
    DOI: 10.1039/C3RA47964A

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