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Synthesis, Characterization and Photophysical Properties of Naphtho[2,3-b]Indolizine-6,11-Dione Derivatives

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Abstract

This communication concerns the synthesis, structural characterization and fluorescent properties of novel naphtho[2,3-b]indolizine-6,11-dione derivatives. The target compound synthesized by one-pot multicomponent reaction between naphthoquinone, indandione and pyridine derivatives. The structures of synthesized compounds were characterized by IR, 1H NMR and 13C NMR analysis. The structure of two compounds was confirmed by single crystal X-ray diffraction. The photophysical properties of synthesized compounds were measured in a variety of organic solvents. The effects of substituents and solvents on UV-vis spectra and fluorescence emission were analyzed. All compounds were showed negative solvatochromism. The fluorescence emission of these derivatives was sensitive to solvent basicity and the large Stokes shifts (up to 129 nm, 4599 cm−1) were observed. The similar multicomponent reaction between naphthoquinone, bindone and pyridine derivatives provide the formation of stable non-fluorescent compound possessing zwitter-ionic structure.

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Notes

  1. For further details, see crystallographic data for 4a deposited at the Cambridge Crystallographic Data Centre as Supplementary Publications with number CCDC 1029264.

  2. For further details, see crystallographic data deposited at the Cambridge Crystallographic Data Centre as Supplementary Publications with number CCDC 1035590

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Acknowledgments

Support for this work was provided by the Riga Technical University through the Scientific Research Project Competition for Young Researchers No 2013/10.

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Authors and Affiliations

  1. Faculty of Materials Science and Applied Chemistry, Riga Technical University, 3/7 P. Valdena St., Riga, LV-1048, Latvia

    Nelli Batenko, Ilze Neibolte, Sergey Belyakov & Raimonds Valters

  2. Latvian Institute of Organic Chemistry, 21 Aizkraukles St., Riga, LV-1006, Latvia

    Sergey Belyakov

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  1. Nelli Batenko
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  2. Ilze Neibolte
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  3. Sergey Belyakov
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  4. Raimonds Valters
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Correspondence to Nelli Batenko.

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Batenko, N., Neibolte, I., Belyakov, S. et al. Synthesis, Characterization and Photophysical Properties of Naphtho[2,3-b]Indolizine-6,11-Dione Derivatives. J Fluoresc 26, 23–29 (2016). https://doi.org/10.1007/s10895-015-1687-x

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