Photoluminescence Dependance of 2-Bromo-3-aminobenzo[de]anthracene-7-one on Solvent Polarity for Potential...

The novel benzanthrone derivative, 2-bromo-3-aminobenzo[de]anthracene-7-one (2-Br-3-NH₂BA), was synthesized and extensively characterized to investigate its photophysical behavior in various solvents. It was prepared through selective bromination of 3-aminobenzanthrone using N-bromosuccinimide in dimethylformamide at -20 °C. Featuring a donor-π-acceptor (D-π-A) structure, 2-Br-3-NH₂BA exhibits pronounced solvatochromism due to the intramolecular charge transfer (ICT) between the amino donor and the carbonyl acceptor groups. Optical measurements conducted in eight solvents of varying polarity revealed a significant bathochromic shift in both absorption and fluorescence emission, with emission maxima red-shifting by over 110 nm from non-polar to polar environments. Corresponding reductions in the optical band gap energies, as calculated from Tauc plots, further support solvent-induced electronic state modulation. Additionally, quantum yield analysis showed higher fluorescence efficiency in non-polar solvents, while polar solvents induced twisted intramolecular charge transfer (TICT), leading to emission quenching. These findings demonstrate the sensitivity of 2-Br-3-NH₂BA to environmental polarity, making it a promising candidate for color-tunable luminescent applications in optoelectronics and sensing. However, further studies in the solid state are required to validate its applicability in device architectures such as OLEDs.