In this paper, we describe the synthesis of two families of compounds type 2-aminonicotinonitrile and 2-aminoisoph- thalonitrile bearing a (benz)imidazole moiety. These compounds were prepared via microwave-promoted three-component reaction of 1-(1-methyl-1H-(benz)imidazole-2-yl)ethylidenedicarbonitrile, enolisable ketone, and propanedinitrile under solvent-free conditions. These two classes of compounds were found to be ﬂuorescently active in solution at room temperature showing an intense blue ﬂuorescence with high ﬂuorescent quantum yield, independently of the excitation wavelength. To explore the origin of absorption band in the title compounds, the TD-DFT/B3LYP/TZ2P approach was used to compute electronic excitation energies, and the corresponding oscillator strengths for two compounds. X-ray crystal structures are reported for two compounds. Graphical abstract 2-Aminonicotinonitrile 2-Aminoisophthalonitrile Keywords (Benz)imidazole Multi-component reaction Fluorescence X-ray diffraction Density functional calculation Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00706-018-2141-y) contains supplementary material, which is available to authorized users. & Ali Belfaitah Institut UTINAM-UMR CNRS 6213, Universite´ de Franche- email@example.com Comte´, 16 Route de Gray, 25030 Besanc¸on, France De´partement de Chimie, Faculte´ des Sciences Exactes, Laboratoire des Produits Naturels d’Origine Ve´ge´tale et de Universite´ des Fre`res Mentouri-Constantine, Synthe`se Organique, De´partement de Chimie, Faculte´ des 25000 Constantine, Algeria Sciences Exactes, Campus de Chaabat Ersas, Universite´ des
Monatshefte für Chemie - Chemical Monthly – Springer Journals
Published: Jan 19, 2018
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