Synthesis of new dyes from imidazo[1, 2-a]pyridine: tautomerism, spectroscopic characterisation, DFT/TD-DFT calculations, atoms in molecules analyses and antibacterial activities. (1st March 2017)

• Record Type: Journal Article
• Authors: Mohammadi, Samaneh; Pordel, Mehdi; Allameh, Sadegh; Chegini, Hamed
• Is Part Of: Journal of chemical research. Volume 41:Number 3(2017)
• Page Start: 143
• Page End: 148
• Publication Date: 2017-03-01
• Subjects: Chemistry -- Research -- Periodicals; Chemistry -- Periodicals; 540.5
• DOI: 10.3184/174751917X14873588907684
• Languages: English
• ISSNs: 1747-5198

Abstract

The synthesis, optical properties, theoretical calculations and antibacterial activity of a series of new heterocyclic dyes from imidazo[1, 2-a] pyridine are described. The key intermediate 2-[3-(hydroxyimino)imidazo[1, 2-a]pyridin-2(3H)-ylidene]malononitrile was obtained via the nucleophilic substitution of hydrogen in 3-nitroimidazo[1, 2-a]pyridine with malononitrile in basic methanol solution. Tautomerism, oxidation and alkylation studies on the dye led to the synthesis of new heterocyclic indigo-coloured, purple, and orange dyes in good yields. The structures of all newly synthesised compounds were confirmed by spectral and analytical data. The optical properties of the dyes were spectrally characterised and shown to exhibit interesting photophysical properties including high extinction coefficients. Density functional theory calculations of the dyes were performed to provide the optimised geometries and relevant frontier orbitals. Calculated electronic absorption spectra were also obtained by the time-dependent density functional theory method. In addition, electrostatic potential maps and electron density maps of the dyes were evaluated by AIM (atoms in molecules) analysis. Moreover, the new dyes exhibited potent antibacterial activity and their antibacterial activities (MIC) against Gram-positive and Gram-negative bacterial species were determined.