title: Synthesis, Spectral Studies and Quantum-Chemical Investigations on the Powerful Fluorophores: Imidazo[4,5-a]acridines.
abstract: The new 3H-imidazo[4,5-a]acridine-11-carbonitriles were prepared from the reaction of 1-alkyl-5-nitro-1H-benzoimidazoles with 2-(4-methoxyphenyl)acetonitrile and benzyl cyanide by nucleophilic substitution of hydrogen in high yields. Physical spectral and analytical data have confirmed the structures of the synthesized dyes. The optical and solvatochromic properties of these compounds were investigated and the results showed that they show very interesting photophysical properties. Density functional theory (DFT) calculations of fluorescent dyes were performed to provide the optimized geometries and relevant frontier orbitals. Furthermore, intra- and intermolecular interactions in fluorescent imidazo[4,5-a]acridines were evaluated by AIM (Atoms in Molecules) analysis.
authors.affiliation: Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran.
authors.forename: Victoria
authors.initials: V
authors.lastname: Maroofi
authors.affiliation: Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran. mehdipordel58@yahoo.com.
authors.forename: Mehdi
authors.initials: M
authors.lastname: Pordel
authors.affiliation: Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran.
authors.forename: Hamed
authors.initials: H
authors.lastname: Chegini
authors.affiliation: Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran.
authors.forename: Shirin
authors.initials: S
authors.lastname: Ramezani
mesh_terms: D000166:Acridines / Q000138:chemical synthesis* / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D011789:Quantum Theory; D013057:Spectrum Analysis
chemical_list: D000166:Acridines; D005456:Fluorescent Dyes; D007093:Imidazoles; C029899:imidazole
keywords: 5-Nitro-1H-benzimidazole; AIM analysis; Density functional theory; Emission and absorption spectra; Fluorescence; Imidazo[4,5-a]acridine