Photoluminescence Dependance of 2-Bromo-3-aminobenzo[<i>de</i>]anthracene-7-one on Solvent Polarity for Potential Applications in Color-Tunable Optoelectronics
The novel benzanthrone derivative, 2-bromo-3-aminobenzo[<i>de</i>]anthracene-7-one (2-Br-3-NH<sub>2</sub>BA), was synthesized and extensively characterized to investigate its photophysical behavior in various solvents. It was prepared through selective bromination of 3-aminob...
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| Main Authors: | , , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2025-06-01
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| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/30/13/2677 |
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| Summary: | The novel benzanthrone derivative, 2-bromo-3-aminobenzo[<i>de</i>]anthracene-7-one (2-Br-3-NH<sub>2</sub>BA), 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-NH<sub>2</sub>BA 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-NH<sub>2</sub>BA 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. |
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| ISSN: | 1420-3049 |