Synthesis and structural properties of 2-((10-alkyl-10H-phenothiazin-3-yl)methylene)malononitrile derivatives; a combined experimental and theoretical insight

Abstract

BackgroundDonor acceptor moieties connected through π-conjugated bridges i.e. D-π-A, in order to facilitate the electron/charge transfer phenomenon, have wide range of applications. Many classes of organic compounds, such as cyanine, coumarin carbazole, indoline, perylene, phenothiazine, triphenylamine, tetrahydroquinoline and pyrrole can act as charge transfer materials. Phenothiazines have been extensively studied as electron donor candidates due to their potential applications as electrochemical, photovoltaic, photo-physical and DSSC materials.ResultsTwo phenothiazine derivatives, 2-((10-hexyl-10H-phenothiazin-3-yl)methylene)malononitrile (3a) and 2-((10-octyl-10H-phenothiazin-3-yl)methylene)malononitrile (3b) have been synthesized in good yields and characterized by various spectroscopic techniques like FT-IR, UV–vis, 1H-NMR, 13C-NMR, and finally confirmed by single crystal X-ray diffraction studies. Density functional theory (DFT) calculations have been performed to compare the theoretical results with the experimental and to probe structural properties. In order to investigate the excited state stabilities the absorption studies have been carried out experimentally as well as theoretically.ConclusionsCompound 3a crystallises as monoclinic, P2 (1)/a and 3b as P-1. The X-ray crystal structures reveal that asymmetric unit contains one independent molecule in 3a, whereas 3b exhibits a very interesting behavior in having a higher Z value of 8 and four independent molecules in its asymmetric unit. The molecular electrostatic potential (MEP) mapped over the entire stabilized geometries of the molecules indicates the potential sites for chemical reactivities. Furthermore, high first hyperpolarizability values entitle these compounds as potential candidates in photonic applications.Graphical abstractPhenothiazines; a comparison of experimental and theoretical analysisElectronic supplementary materialThe online version of this article (doi:10.1186/s13065-016-0158-z) contains supplementary material, which is available to authorized users.

A new phenothiazine-based selective visual and fluorescent sensor for cyanide

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Synthesis, optical properties and DFT-TDDFT computational study of phenothiazine dye: donor-acceptor molecules

“…The solvents and chemicals used in the current investigation, including potassium hydroxide, 10-pohenothiazine, 1-bromohexane and potassium iodide, were provided by Sigma-Aldrich. Using the previously reported method, 10-hexyl-10H-phenothiazine and 10-hexyl-10H-phenothiazine-3-carbaldehyde, were synthesized in my previous article (El-Shishtawy et al , 2016).…”

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Design, synthesis, structure elucidation, antimicrobial, molecular docking, and SAR studies of novel urea derivatives bearing tricyclic aromatic hydrocarbon rings

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