Novel amidine derivatives of benzanthrone: Effect of bromine atom on the spectral parameters

Novel amidine derivatives of benzanthrone: Effect of bromine atom on the spectral parameters

Several new substituted amidine derivatives of benzanthrone were synthesized by condensation reaction from 2-bromo-3-aminobenzo[de]anthracen-7-one and appropriate aromatic or aliphatic amides. The novel benzanthrone derivatives were characterized by TLC analysis, NMR, IR, MS, UV/Vis, and fluorescenc...

Full description

Saved in:
Bibliographic Details
Published in:Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Vol. 202; pp. 41 - 49
Main Authors: Kirilova, E.M., Puckins, A.I., Romanovska, E., Fleisher, M., Belyakov, S.V.
Format: Journal Article
Language:English
Published: Elsevier B.V 05-09-2018
Subjects:
Benzanthrone dyes
Crystal structure
Dipole moment
Fluorescence
Solvatofluochromism
Fluorescence
Solvatofluochromism
Dipole moment
Benzanthrone dyes
Crystal structure
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Several new substituted amidine derivatives of benzanthrone were synthesized by condensation reaction from 2-bromo-3-aminobenzo[de]anthracen-7-one and appropriate aromatic or aliphatic amides. The novel benzanthrone derivatives were characterized by TLC analysis, NMR, IR, MS, UV/Vis, and fluorescence spectroscopy. The obtained derivatives have yellow or orange fluorescence in organic solvents. The solvent effect on photophysical behaviors of these dyes was investigated, and the results showed that the introduction of a bromine atom causes a blue-shift of the absorption and emission bands and decrease in the fluorescent quantum yield in comparison with unbromated analogues. The difference in the excited state and the ground state dipole moments was estimated by using the variation of Stokes shift and by semiempirical molecular calculations. The crystal structure and packing of four novel dyes has been revealed by the X-ray single crystal structure analysis. [Display omitted] •Novel solvatofluochromic benzanthrone dyes with amidino group and bromine atom were synthesized.•Introduction of a bromine atom causes a blue-shift of the absorption and emission bands and quenches the luminescence.•π-π interactions in crystals are weaker than those in unbromated compounds.
ISSN:1386-1425
DOI:10.1016/j.saa.2018.05.029