Switchable fluorescence by click reaction of a novel azidocarbazole dye

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.