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 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy Elsevier

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

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Publisher
Elsevier
Copyright
Copyright © 2018 Elsevier B.V.
ISSN
1386-1425
D.O.I.
10.1016/j.saa.2018.05.029
Publisher site
See Article on Publisher Site

Abstract

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.

Journal

Spectrochimica Acta Part A: Molecular and Biomolecular SpectroscopyElsevier

Published: Sep 5, 2018

References

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