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Structure and properties of a series of 2-cinnamoyl-1,3-indandiones and their metal complexes

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Abstract

A series of seven 2-cinnamoyl-1,3-indandiones and their metal(II) complexes were synthesized and characterized by means of spectroscopic (IR, NMR, electron absorption and emission spectroscopy) and/or single-crystal X-ray diffraction methods. The optical spectra of the organic compounds show very strong absorption in the visible region and weak fluorescence with moderate to strong Stokes shift. The effect of concentration, water addition and metal ion complexation on the optical properties was also studied. In search of potential practical application, the complexation of 2-cinnamoyl-1,3-indandiones with metal(II) ions was investigated. A series of non-charged complexes with Cu(II), Cd(II), Zn(II), Co(II) and Ni(II) was isolated and analyzed by elemental analyses and IR. Most of the complexes show presence of water molecules, most probably coordinated to the metal ion, thus forming octahedral geometry. For the paramagnetic Cu(II) complexes a distorted, flattened tetrahedral structure is proposed, basing on the EPR data. The optical properties of the metal complexes, however, do not differ appreciably from those of the free ligands.

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Acknowledgments

Financial support by the Ministry of Science and Technology of the Republic of Croatia (Grant No. 098-1191344-2943) and Plovdiv University (Grant No. NI-2011-HF-007) are gratefully acknowledged.

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Authors and Affiliations

  1. Faculty of Chemistry, University of Sofia, 1, J. Bourchier av., 1164, Sofia, Bulgaria

    Anife Ahmedova & Mariana Mitewa

  2. Faculty of Chemistry, University of Plovdiv, 24, Tzar Assen str., 4000, Plovdiv, Bulgaria

    Petja Marinova

  3. Laboratory of General Chemistry, Department of Applied Chemistry, Faculty of Textile Technology, University of Zagreb, Prilaz baruna Filipovića 28a, HR-10000, Zagreb, Croatia

    Gordana Pavlović

  4. Institute of Organic Chemistry and with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev str. bl.9, Sofia, 1113, Bulgaria

    Maya Guncheva

  5. Rousse University, Technological Branch, Razgrad, 3, Aprilsko vastanie str., 7200, Razgrad, Bulgaria

    Neyko Stoyanov

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  1. Anife Ahmedova
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  2. Petja Marinova
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  3. Gordana Pavlović
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  4. Maya Guncheva
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  5. Neyko Stoyanov
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  6. Mariana Mitewa
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Correspondence to Anife Ahmedova.

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Ahmedova, A., Marinova, P., Pavlović, G. et al. Structure and properties of a series of 2-cinnamoyl-1,3-indandiones and their metal complexes. J IRAN CHEM SOC 9, 297–306 (2012). https://doi.org/10.1007/s13738-011-0024-9

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  • DOI: https://doi.org/10.1007/s13738-011-0024-9

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