title: Fluorescent substituted amidines of benzanthrone: synthesis, spectroscopy and quantum chemical calculations.
abstract: Several new substituted amidine derivatives of benzanthrone were synthesized by a condensation reaction from 3-aminobenzo[de]anthracen-7-one and appropriate aromatic and aliphatic amides. The obtained derivatives have a bright yellow or orange fluorescence in organic solvents and in solid state. The novel benzanthrone derivatives were characterized by TLC analysis, (1)H NMR, IR, MS, UV/vis, and fluorescence spectroscopy. The solvent effect on photophysical behaviors of these dyes was investigated, and the results showed that the Stoke's shift increased, whereas quantum yield decreased with the growth of the solvent polarity. The structure of some dyes was confirmed by the X-ray single crystal structure analysis. AM1, ZINDO/S and ab initio calculations using Gaussian software were carried out to estimate the electron system of structures. The calculations show planar configurations for the aromatic core of these compounds and two possible orientations of amidine substituents. The calculation results correlate well with red-shifted absorption and emission spectra of compounds.
authors.affiliation: Laboratory of Microbial Storage Product Research, Institute of Microbiology and Biotechnology, University of Latvia, Kronvalda blvd. 4, Riga LV-1586, Latvia. svetago7@gmail.com
authors.forename: Svetlana
authors.initials: S
authors.lastname: Gonta
authors.forename: Maris
authors.initials: M
authors.lastname: Utinans
authors.forename: Georgii
authors.initials: G
authors.lastname: Kirilov
authors.forename: Sergey
authors.initials: S
authors.lastname: Belyakov
authors.forename: Irena
authors.initials: I
authors.lastname: Ivanova
authors.forename: Mendel
authors.initials: M
authors.lastname: Fleisher
authors.forename: Valerij
authors.initials: V
authors.lastname: Savenkov
authors.forename: Elena
authors.initials: E
authors.lastname: Kirilova
mesh_terms: D000578:Amidines / Q000138:chemical synthesis / Q000737:chemistry*; D001551:Benz(a)Anthracenes / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D000578:Amidines; D001551:Benz(a)Anthracenes; D005456:Fluorescent Dyes; C012768:benzanthrone