Click 1,2,3-triazole derived fluorescent scaffold by mesoionic carbene-nitrene cyclization: an experimental and theoretical studyElectronic supplementary information (ESI) available: Supplementary spectra, crystallographic details, xyz coordinates, computational analysis of IR spectra, and 1H and 13C NMR spectra of the new compounds are provided. CCDC 1856372. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8nj04070b

• Main Authors: Bouchemella, Khadidja, Fauché, Kévin, Anak, Barkahem, Jouffret, Laurent, Bencharif, Mustapha, Cisnetti, Federico
• Format: Journal Article
• Language: English
• Published: 19.11.2018
• ISSN: 1144-0546; 1369-9261
• DOI: 10.1039/c8nj04070b

We describe a set of three fluorescent mesoionic benzo[4,5]imidazo-3-ide-[1,2- c ]-2-alkyl-1,2,3-triazol-2-ium compounds obtained through a simple, concise and efficient synthetic sequence featuring a copper-catalyzed carbene-nitrene cyclization. The compounds were characterized by fluorescence spectroscopy highlighting promising photophysical properties in terms of quantum yields and Stokes shifts. Experimental properties were rationalized by a computational DFT and TD-DFT approach with excellent agreement with structural and spectroscopic data. Easily accessible compact triazole-based fluorescent compounds were characterized spectroscopically and their properties modeled by computational methods.