Single crystal X-ray structure and optical properties of anthraquinone-based dyes

• Published in: Chemical papers 2010, Vol.64 (5), p.645-651
• Main Authors: Kurtoglu, Nurcan, Aslantaş, Mehmet, Zengin, Huseyin, Şahin, Ertan, Kurtoglu, Mukerrem
• Format: Article
• Language: English
• Subjects: anthraquinone; antimicrobial dye; Biochemistry; Biotechnology; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; hydrogen bonding; Industrial Chemistry/Chemical Engineering; Materials Science; Medicinal Chemistry; Original Paper; photoluminescence; X-ray crystal structure
• ISSN: 0366-6352; 1336-9075; 1336-9075
• DOI: 10.2478/s11696-010-0037-3

This study focuses on the preparation, single crystal X-ray diffraction, characterization, and optical properties of some anthraquinone-based dyes. The anthraquinone-based antimicrobial dye N -{2-[(9,10-dioxo-9,10-dihydroanthracen-1-yl)amino]-2-oxoethyl}- N,N -dimethylbutan-1-aminium chloride monohydrate ( III ) was obtained from 1-aminoanthraquinone ( I ) via 2-chloro- N -(9,10-dioxo-9,10-dihydroanthracen-1-yl)acetamide ( II ) using known preparation and characterization methods. Single crystal X-ray diffraction analysis of III revealed a monoclinic system, space group P 2 1 /n, Z = 4. Photoluminescence properties of anthraquinone dyes I–III were also investigated. These dyes gave an intense emission (λ max = 341 nm) upon the irradiation by UV light and showed photoluminescence quantum yields of 73 %, 66 %, and 61 % with long excited-state lifetimes of 6.87 ns, 6.14 ns, and 5.69 ns, respectively. These anthraquinone dyes are of interest as an organic light emitting material for electroluminescent devices.