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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 und Mukerrem Kurtoglu
Veröffentlicht/Copyright: 14. August 2010
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Chemical Papers
Aus der Zeitschrift Chemical Papers Band 64 Heft 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

[1] Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G., & Taylor, R. (1987). Tables of bond lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compounds. Journal of Chemistry Society, Perkin Transaction 2, 1987, 1–19. DOI: 10.1039/P298700000S1. http://dx.doi.org/10.1039/p298700000s110.1039/p298700000s1Suche in Google Scholar

[2] Aslantas, M., Kurtoglu, N., Sahin, E., & Kurtoglu, M. (2007). 4-[(E)-Phenyldiazenyl]-2-[(E)-phenyliminomethyl]phenol. Acta Crystallographica Section E, E63, o3637. DOI: 10.1107/S1600536807036197. http://dx.doi.org/10.1107/S160053680703619710.1107/S1600536807036197Suche in Google Scholar

[3] Balabanova, M., Popova, L., & Tchipeva, R. (2003). Dyes in dermatology. Clinics in Dermatology, 21, 2–6. DOI:10.1016/S0738-081X(02)00330-9. http://dx.doi.org/10.1016/S0738-081X(02)00330-910.1016/S0738-081X(02)00330-9Suche in Google Scholar

[4] Berghot, M. A., & Moawad, E. B. (1995). Synthesis of novel substituted anthra[1,9-bc]pyridin-6-ones. Bollettino Chimico Farmaceutico, 134, 564–568. Suche in Google Scholar

[5] Birbiçer, N., Kurtoğlu, M., & Serin, S. (1999). Synthesis of two new azo ligands containing polyoxyethylene glycol and their complexes with Ni(II), Cu(II) and Co(II). Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 29, 1353–1364. DOI: 10.1080/00945719909351704. 10.1080/00945719909351704Suche in Google Scholar

[6] Boonnak, N., Chantrapromma, S., Fun, H. K., Anjum, S., Ali, S., Atta-ur-Rahman, & Karalai, C. (2005). 3-(3,7-Dimethylocta-2,6-dienyloxy)-1,8-dihydroxy-6-methyl-9,10-anthraquinone. Acta Crystallographica Section E, E61, o410–o412. DOI: 10.1107/S1600536805001674. http://dx.doi.org/10.1107/S160053680500167410.1107/S1600536805001674Suche in Google Scholar

[7] Chen, T. R., Chen, J. D., Keng, T. C., & Wang, J. C. (2001). A new pyridylamine for blue light electroluminescent devices. Tetrahedron Letter, 42, 7915–7917. DOI: 10.1016/S0040-4039(01)01693-8. http://dx.doi.org/10.1016/S0040-4039(01)01693-810.1016/S0040-4039(01)01693-8Suche in Google Scholar

[8] Dahiya, P., Choudhury, S. D., Maity, D. K., Mukherjee, T., & Pal, H. (2008). Solvent polarity induced structural changes in 2,6-diamino-9,10-anthraquinone dye. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 69, 134–141. DOI: 10.1016/j.saa.2007.03.018. http://dx.doi.org/10.1016/j.saa.2007.03.01810.1016/j.saa.2007.03.018Suche in Google Scholar PubMed

[9] Farrugia, L. J. (1997). ORTEP-3 for Windows — a version of ORTEP-III with a graphical user interface (GUI). Journal of Applied Crystallography, 30, 565. DOI: 10.1107/S0021889897003117. http://dx.doi.org/10.1107/S002188989700311710.1107/S0021889897003117Suche in Google Scholar

[10] Gilbert, A., & Baggott, J. (1991). Essentials of molecular photochemistry. Boca Raton, FL, USA: CRC Press. Suche in Google Scholar

[11] Gordon, P. F., & Gregory, P. (1983). Organic chemistry in colour (p. 162). Berlin, Germany: Springer. 10.1515/9783112541746Suche in Google Scholar

[12] Gregory, P. (1991). High-technology applications of organic colorants. New York, NY, USA: Plenum Press. 10.1007/978-1-4615-3822-6Suche in Google Scholar

[13] Guilbault, G. G. (Ed.) (1990). Practical fluorescence (2nd ed.). New York, NY, USA: Marcel Dekker. Suche in Google Scholar

[14] Kirk, R. E., & Othmer, D. F. (1993). Dyes, anthraquinones. In J. I. Kroschwitz, & M. Howe-Grant (Eds.), Kirk-Othmer encyclopedia of chemical technology (4th ed., Vol. 4, pp. 653–666). New York, NY, USA: Wiley. Suche in Google Scholar

[15] Kocaokutgen, H., Gür, M., Soylu, M. S., & Lönnecke, P. (2005). Spectroscopic, thermal and crystal structure properties of novel (E)-2,6-dimethyl-4-(4-tert-butylphenyldiazenyl)phenyl acrylate dye. Dyes and Pigments, 67, 99–103. DOI: 10.1016/j.dyepig.2004.09.021. http://dx.doi.org/10.1016/j.dyepig.2004.09.02110.1016/j.dyepig.2004.09.021Suche in Google Scholar

[16] Kulkarni, A. P., Zhu, Y., & Jenekhe, S. A. (2005). Quinoxalinecontaining polyfluorenes: Synthesis, photophysics, and stable blue electroluminescence. Macromolecules, 38, 1553–1363. DOI: 10.1021/ma048118d. http://dx.doi.org/10.1021/ma048118d10.1021/ma048118dSuche in Google Scholar

[17] Kurtoğlu, M., & Baydemir, S. A. (2007). Studies on mononuclear transition metal chelates derived from a novel (E, E)-dioxime: synthesis, characterization and biological activity. Journal of Coordination Chemistry, 60, 655–665. DOI:10.1080/00958970600896076. http://dx.doi.org/10.1080/0095897060089607610.1080/00958970600896076Suche in Google Scholar

[18] Kurtoğlu, M., Birbiçer, N., Kimyonen, Ü., & Serin, S. (1999a). Determination of pKa values of some azo dyes in acetonitrile with perchloric acid. Dyes and Pigments, 41, 143–147. DOI: 10.1016/S0143-7208(98)00077-1. http://dx.doi.org/10.1016/S0143-7208(98)00077-110.1016/S0143-7208(98)00077-1Suche in Google Scholar

[19] Kurtoğlu, M., İspir, E., Kurtoğlu, N., & Serin, S. (2008). Novel vic-dioximes: Synthesis, complexation with transition metal ions, spectral studies and biological activity. Dyes and Pigments, 77, 75–80. DOI: 10.1016/j.dyepig.2007.03.010. http://dx.doi.org/10.1016/j.dyepig.2007.03.01010.1016/j.dyepig.2007.03.010Suche in Google Scholar

[20] Kurtoğlu, N., Kurtoğlu, M., & Serin, S. (1999b). Synthesis and characterisation of some novel Schiff base metal complexes with polyoxyethylene glycols as substituents. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 29, 1779–1791. DOI: 10.1080/00945719909351735. 10.1080/00945719909351735Suche in Google Scholar

[21] Leadbetter, P. W., & Leaver, A. T. (1989). Disperse dyes — the challenge of the 1990s. Review of Progress in Coloration, 19, 33–39. http://dx.doi.org/10.1111/j.1478-4408.1989.tb03758.x10.1111/j.1478-4408.1989.tb03758.xSuche in Google Scholar

[22] Liu, J., & Sun, G. (2008). The synthesis of novel cationic anthraquinone dyes with high potent antimicrobial activity. Dyes and Pigments, 77, 380–386. DOI: 10.1016/j.dyepig.2007.06.009. http://dx.doi.org/10.1016/j.dyepig.2007.06.00910.1016/j.dyepig.2007.06.009Suche in Google Scholar

[23] Ma, M., Sun, Y., & Sun, G. (2003). Antimicrobial cationic dyes: part 1: synthesis and characterization. Dyes and Pigments, 58, 27–35. DOI: 10.1016/S0143-7208(03)00025-1. http://dx.doi.org/10.1016/S0143-7208(03)00025-110.1016/S0143-7208(03)00025-1Suche in Google Scholar

[24] Malone, J. F., Andrews, S. J., Bullock, J. F., & Docherty, R. (1996). The solid state structure of CI Disperse Orange 44. Dyes and Pigments, 30, 183–200. DOI: 10.1016/0143-7208(95)00076-3. http://dx.doi.org/10.1016/0143-7208(95)00076-310.1016/0143-7208(95)00076-3Suche in Google Scholar

[25] Martelli, S., Dzieduszycka, M., Stefanska, B., Gracz, M. B., & Borowski, E. (1988). Synthesis and antineoplastic evaluations of 1,4-bis(aminoalkanamido)-9,10-anthracenediones. Journal of Medicinal Chemistry, 31, 1956–1959. DOI: 10.1021/jm00118a015. http://dx.doi.org/10.1021/jm00118a01510.1021/jm00118a015Suche in Google Scholar PubMed

[26] Nardelli, M. (1995). PARST95 — an update to PARST: a system of Fortran routines for calculating molecular structure parameters from the results of crystal structure analyses. Journal of Applied Crystallography, 28, 659. DOI: 10.1107/S0021889895007138. http://dx.doi.org/10.1107/S002188989500713810.1107/S0021889895007138Suche in Google Scholar

[27] Øllgaard, H., Frost, L., Galster, J., & Hansen, O. C. (1999). Survey of azo-colorants in Denmark: Consumption, use, health and environmental aspects. Copenhagen: Ministry of Environment and Energy, Danish Environmental Protection Agency. (Miljøprojekt No. 509, No. XX 1998, pp. 147–290). Suche in Google Scholar

[28] Osaheni, J. A., & Jenekhe, S. A. (1994). Enhancement of luminescence in polymer nanocomposites. Chemistry Materials, 6, 1906–1909. DOI: 10.1021/cm00047a002. http://dx.doi.org/10.1021/cm00047a00210.1021/cm00047a002Suche in Google Scholar

[29] Patrauchan, M. A., & Oriel, P. J. (2003). Degradation of benzyldimethylalkylammonium chloride by Aeromonas hydrophila sp. K. Journal of Applied Microbiology, 94, 266–272. DOI: 10.1046/j.1365-2672.2003.01829.x. http://dx.doi.org/10.1046/j.1365-2672.2003.01829.x10.1046/j.1365-2672.2003.01829.xSuche in Google Scholar PubMed

[30] Peters, A. T., & Freeman, H. S. (Eds.) (1991). Colour chemistry: The design and synthesis of organic dyes and pigments (pp. 193–195). Barking, UK: Elsevier. Suche in Google Scholar

[31] Pu, Y. J., Kurata, T., Soma, M., Kido, J., & Nishide, H. (2004). Triphenylamine- and oxadiazole-substituted poly(1,4-phenylenevinylene) s: synthesis, photo-, and electroluminescent properties. Synthetic Metals, 143, 207–214. DOI: 10.1016/j.synthmet.2003.12.003. http://dx.doi.org/10.1016/j.synthmet.2003.12.00310.1016/j.synthmet.2003.12.003Suche in Google Scholar

[32] Rembold, M. W., & Kramer, H. E. A. (1980). The role of anthraquinonoid dyes in the catalytic fading’of dye mixtures — substituent-dependent triplet yield of diaminoanthraquinones. Journal of the Society Dyers and Colourists, 96, 122–126. DOI: 10.1111/j.1478-4408.1980.tb03518.x. http://dx.doi.org/10.1111/j.1478-4408.1980.tb03518.x10.1111/j.1478-4408.1980.tb03518.xSuche in Google Scholar

[33] Rigaku/MSC. (2005). CrystalClear [computer software]. Rigaku/MSC Inc.: The Woodlands, TX, USA. Suche in Google Scholar

[34] Sadeghi-Aliabadi, H., Tabarzadi, M., & Zarghi, A. (2004). Synthesis and cytotoxic evaluation of two novel anthraquinone derivatives. Il Farmaco, 59, 645–649. DOI: 10.1016/j.farmac.2004.03.006. http://dx.doi.org/10.1016/j.farmac.2004.03.00610.1016/j.farmac.2004.03.006Suche in Google Scholar PubMed

[35] Serin, S., & Kurtoğlu, M. (1994). Potentiometric titrations of some azo dyes containing a hydroxy group with tetrabutylammonium hydroxide in acetonitrile. Analyst, 119, 2213–2215. DOI: 10.1039/AN9941902213. http://dx.doi.org/10.1039/an994190221310.1039/AN9941902213Suche in Google Scholar

[36] Sheldrick, G. M. (1997a). SHELXS-97. Program for crystal structure solution. Göttingen, Germany: University of Göttingen. Suche in Google Scholar

[37] Sheldrick, G. M. (1997b). SHELXL-97. Program for refinement of crystal structures. Göttingen, Germany: University of Göttingen. Suche in Google Scholar

[38] Shinar, J. (Ed.) (2004). Organic light-emitting devices: A survey. New York, NY, USA: Springer. 10.1007/978-0-387-21720-8Suche in Google Scholar

[39] Singh, K., Mahajan, A., & Robinson, W. T. (2007). Single crystal X-ray structure analysis of some heterocyclic monoazo disperse dyes. Dyes and Pigments, 74, 95–102. DOI:10.1016/j.dyepig.2006.01.018. http://dx.doi.org/10.1016/j.dyepig.2006.01.01810.1016/j.dyepig.2006.01.018Suche in Google Scholar

[40] Spek, A. L. (2003). PLATON, a multipurpose crystallographic tool. Utrecht, The Netherlands: University of Utrecht. Suche in Google Scholar

[41] Sun, G., & Ma, M. (2005). U.S. Patent Application No. US 2005/0011012 A1. Arlington, VA, USA: United States Patent and Trademark Office. Suche in Google Scholar

[42] Temel, A., Özbey, S., & Ertan, N. (1996). Crystal structure of hydrazone form of 1-butyl-3-cyano-6-hydroxy-4-methyl-5-(2-thiazolylazo)-2-(1H)-pyridone. Dyes and Pigments, 32, 237–244. DOI: 10.1016/S0143-7208(96)00028-9. http://dx.doi.org/10.1016/S0143-7208(96)00028-910.1016/S0143-7208(96)00028-9Suche in Google Scholar

[43] Wilson, A. J. C. (Ed.) (1995). International tables for crystallography: Mathematical, physical and chemical tables (2nd ed., Vol. C). Dordrecht, The Netherlands: Kluwer. Suche in Google Scholar

[44] Yang, W., You, X. L., Zhong, Y., & Zhang, D. C. (2007). The crystal structure of 4-[(2-methoxy-4-nitro-phenylazo)-phenyl]-dimethyl-amine. Dyes and Pigments, 73, 317–321. DOI: 10.1016/j.dyepig.2005.11.013. http://dx.doi.org/10.1016/j.dyepig.2005.11.01310.1016/j.dyepig.2005.11.013Suche in Google Scholar

[45] Zhao, D. X., Li, W. L., Hong, Z. R., Liu, X., Liang, C., & Zhao, D. (1999). White light emitting organic electroluminescent devices using lanthanide dinuclear complexes. Journal of Luminescence, 82, 105–109. DOI: 10.1016/S0022-2313(99)00038-1. http://dx.doi.org/10.1016/S0022-2313(99)00038-110.1016/S0022-2313(99)00038-1Suche in Google Scholar

[46] Zhu, J. C., Liang, Y., Wang, H. S., Pan, Y. M., & Zhang, Y. (2007). 1,3,8-Trihydroxy-6-methylanthraquinone monohydrate. Acta Crystallographica Section E, E63, 233–235. DOI: 10.1107/S1600536806049178. 10.1107/S1600536806049178Suche in Google Scholar

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

© 2010 Institute of Chemistry, Slovak Academy of Sciences

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  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
Schlagwörter für diesen Artikel
anthraquinone; antimicrobial dye; X-ray crystal structure; hydrogen bonding; photoluminescence

Artikel in diesem Heft

  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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