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

  • Nurcan Kurtoglu EMAIL logo , Mehmet Aslantaş , Huseyin Zengin , Ertan Şahin and Mukerrem Kurtoglu
Published/Copyright: August 14, 2010
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Chemical Papers
From the journal Chemical Papers Volume 64 Issue 5

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.

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

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Published Online: 2010-8-14
Published in Print: 2010-10-1

© 2010 Institute of Chemistry, Slovak Academy of Sciences

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  8. Polyamidoamine dendrimer and dextran conjugates: preparation, characterization, and in vitro and in vivo evaluation
  9. Morphological characteristics of modified freeze-dried poly(N-isopropylacrylamide) microspheres studied by optical microscopy, SEM, and DLS
  10. Photophysical properties of novel ferrocenyl quinoline derivatives with red emission in solutions and polymeric matrices
  11. Preparation and characterization of hydrogels based on acryloyl end-capped four-arm star-shaped poly(ethylene glycol)-branched-oligo(l-lactide) via Michael-type addition reaction
  12. ArF laser photolytic deposition and thermal modification of an ultrafine chlorohydrocarbon
  13. Asymmetric synthesis of machilin C and its analogue
  14. Synthesis and study of some new N-substituted imide derivatives as potential antibacterial agents
  15. Single crystal X-ray structure and optical properties of anthraquinone-based dyes
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  17. Factors influencing aggregation behavior of poly(γ-benzyl l-glutamate)-graft-poly(ethylene glycol) copolymer in mixed solvents
  18. Chemical evaluation of Fallopia species leaves and antioxidant properties of their non-cellulosic polysaccharides
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https://doi.org/10.2478/s11696-010-0037-3
Keywords for this article
anthraquinone; antimicrobial dye; X-ray crystal structure; hydrogen bonding; photoluminescence

Articles in the same Issue

  1. A deuterium-palladium electrode as a new sensor in non-aqueous solutions: potentiometric titration of weak acids in acetonitrile and benzonitrile
  2. Chemical variability of Artemisia herba-alba Asso essential oils from East Morocco
  3. Ag and Cu loaded on TiO2/graphite as a catalyst for Escherichia coli-contaminated water disinfection
  4. Direct electrochemistry and electrocatalysis of horseradish peroxidase immobilized in hyaluronic acid and single walled carbon nanotubes composite film
  5. Biological buffered saline solution as solvent in agar-carbomer hydrogel synthesis
  6. GC/MS analysis of gaseous degradation products formed during extrusion blow molding process of PE films
  7. Preparation, spectral, thermal, and biological properties of zinc(II) 4-chloro- and 5-chlorosalicylate complexes with methyl 3-pyridylcarbamate and phenazone
  8. Polyamidoamine dendrimer and dextran conjugates: preparation, characterization, and in vitro and in vivo evaluation
  9. Morphological characteristics of modified freeze-dried poly(N-isopropylacrylamide) microspheres studied by optical microscopy, SEM, and DLS
  10. Photophysical properties of novel ferrocenyl quinoline derivatives with red emission in solutions and polymeric matrices
  11. Preparation and characterization of hydrogels based on acryloyl end-capped four-arm star-shaped poly(ethylene glycol)-branched-oligo(l-lactide) via Michael-type addition reaction
  12. ArF laser photolytic deposition and thermal modification of an ultrafine chlorohydrocarbon
  13. Asymmetric synthesis of machilin C and its analogue
  14. Synthesis and study of some new N-substituted imide derivatives as potential antibacterial agents
  15. Single crystal X-ray structure and optical properties of anthraquinone-based dyes
  16. Low-density polyethylene in mixtures of hexane and benzene derivates
  17. Factors influencing aggregation behavior of poly(γ-benzyl l-glutamate)-graft-poly(ethylene glycol) copolymer in mixed solvents
  18. Chemical evaluation of Fallopia species leaves and antioxidant properties of their non-cellulosic polysaccharides
  19. Rapid synthesis and bioactivities of 3-(nitromethylene)indolin-2-one analogues
  20. ZnO nanorods catalyzed N-alkylation of piperidin-4-one, 4(3H)-pyrimidone, and ethyl 6-chloro-1,2-dihydro-2-oxo-4-phenylquinoline-3-carboxylate
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