New highly fluorescent hybrids (benz)imidazol-2-aminonicotinonitrile and -2-aminoisophthalonitrile: synthesis, characterization, fluorescence study, and theoretical calculations

New highly fluorescent hybrids (benz)imidazol-2-aminonicotinonitrile and... 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- abelbelfaitah@yahoo.fr 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 http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Monatshefte für Chemie - Chemical Monthly Springer Journals

New highly fluorescent hybrids (benz)imidazol-2-aminonicotinonitrile and -2-aminoisophthalonitrile: synthesis, characterization, fluorescence study, and theoretical calculations

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Publisher
Springer Vienna
Copyright
Copyright © 2018 by Springer-Verlag GmbH Austria, part of Springer Nature
Subject
Chemistry; Chemistry/Food Science, general; Organic Chemistry; Inorganic Chemistry; Analytical Chemistry; Physical Chemistry; Theoretical and Computational Chemistry
ISSN
0026-9247
eISSN
1434-4475
D.O.I.
10.1007/s00706-018-2141-y
Publisher site
See Article on Publisher Site

Abstract

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- abelbelfaitah@yahoo.fr 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

Journal

Monatshefte für Chemie - Chemical MonthlySpringer Journals

Published: Jan 19, 2018

References

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