Abstract
We report a synthesis of 3-bromo-9-N′-(N,N-dimethylformamidino)benzanthrone in good yield by a condensation reaction of 3-bromo-9-aminobenzanthrone with dimethylformamide in the presence of phosphorous oxychloride. The structure of the synthesized amidine was characterized by FTIR-ATR, NMR experiments, and elemental analysis. The title compound was analyzed by UV-Vis and fluorescence spectroscopy in various organic solvents.
Highlights
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The literature describes only a few 3,9-disubstituted derivatives [11]. These heterocyclic derivatives were synthetized by nucleophilic substitution of bromine atoms in 3,9-dibromobenzanthrone and exhibit thermally activated delayed deep-red fluorescence [11]
The dye has relatively large Stokes shifts. These characteristics of the prepared amidine demonstrate its potential as a biomedical probe for proteins, lipids, and cells
Summary
The most common substituted benzanthrone derivatives contain an amino group at various positions in the aromatic system. The possibility of replacing hydrogen atoms in the amino group makes it possible to obtain various N-containing derivatives, which are already or may find practical use in the future. The literature describes only a few 3,9-disubstituted derivatives [11] These heterocyclic derivatives were synthetized by nucleophilic substitution of bromine atoms in 3,9-dibromobenzanthrone and exhibit thermally activated delayed deep-red fluorescence [11]. Another possible method for the preparation of 3,9-disubstituted derivatives could be the use of 3-bromo-9aminobenzantrone. We decided to use 3-bromo-9-aminobenzantrone for synthesis of the first amidino derivative and to study its photophysical properties
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