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

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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 (λmax = 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.

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Authors and Affiliations

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

    Nurcan Kurtoglu

  2. Department of Physics, Faculty of Science and Arts, Kahramanmaras Sutcu Imam University, Kahramanmaras, 46050, Turkey

    Mehmet Aslantaş

  3. Department of Chemistry, Faculty of Science and Arts, Kahramanmaras Sutcu Imam University, Kahramanmaras, 46050, Turkey

    Huseyin Zengin & Mukerrem Kurtoglu

  4. Department of Chemistry, Faculty of Science and Arts, Atatürk University, Erzurum, 25240, Turkey

    Ertan Şahin

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  1. Nurcan Kurtoglu
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  2. Mehmet Aslantaş
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  5. Mukerrem Kurtoglu
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Correspondence to Nurcan Kurtoglu.

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Kurtoglu, N., Aslantaş, M., Zengin, H. et al. Single crystal X-ray structure and optical properties of anthraquinone-based dyes. Chem. Pap. 64, 645–651 (2010). https://doi.org/10.2478/s11696-010-0037-3

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