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Switchable fluorescence by click reaction of a novel azidocarbazole dye

Hörner, Anna 1; Volz, Daniel 1; Hagendorn, Tobias 1; Furniss, Daniel 1; Greb, Lutz 1; Ronicke, Franziska 2; Nieger, Martin; Schepers, Ute 2; Bräse, Stefan 2
1 Karlsruher Institut für Technologie (KIT)
2 Institut für Toxikologie und Genetik (ITG), Karlsruher Institut für Technologie (KIT)


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.

Volltext §
DOI: 10.5445/IR/1000046411
DOI: 10.1039/C3RA47964A
Zitationen: 14
Zitationen: 15
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Toxikologie und Genetik (ITG)
Universität Karlsruhe (TH) – Interfakultative Einrichtungen (Interfakultative Einrichtungen)
Karlsruhe School of Optics & Photonics (KSOP)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2014
Sprache Englisch
Identifikator ISSN: 2046-2069
KITopen-ID: 1000046411
HGF-Programm 47.02.01 (POF II, LK 01) Synth. biomimetische Werkzeuge ITG
Erschienen in RSC Advances
Verlag Royal Society of Chemistry (RSC)
Band 4
Heft 23
Seiten 11528-11534
Bemerkung zur Veröffentlichung RSC geförderter Open Access-Artikel
Nachgewiesen in Scopus
Web of Science
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