ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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

Nurcan Kurtoglu, Mehmet Aslantaş, Huseyin Zengin, Ertan Şahin, and Mukerrem Kurtoglu

Department of Textile Engineering, Faculty of Engineering and Architecture, Kahramanmaras Sutcu Imam University, Kahramanmaras, 46050 Turkey

E-mail: nkurtoglu@ksu.edu.tr

Abstract: 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 P2₁/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.

Keywords: anthraquinone - antimicrobial dye - X-ray crystal structure - hydrogen bonding - photoluminescence

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-010-0037-3

Chemical Papers 64 (5) 645–651 (2010)