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Novel β-ketoenamines versus azomethines for organic electronics: characterization of optical and electrochemical properties supported by theoretical studies

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Abstract

A simple and rapid synthesis of six new, stable β-ketoenamines by coupling 3-amino-1,8-naphthalimide derivatives with 2-(4-pyrimidinyl)-malondialdehyde in the presence of trifluoroacetic acid was developed. Two of the synthesized 3-amino-1,8-naphthalimide derivatives were condensed with 9H-fluorene-2-carboxaldehyde, resulting in azomethine products. The structure of obtained compounds was confirmed by 1H and 13C NMR, COSY, HMQC, FTIR spectroscopy and elemental analysis. The photophysical, electrochemical and thermal properties of the compounds were investigated. Additionally, calculations using density functional theory were performed to obtain the optimized ground-state geometry and distribution of the HOMO and LUMO levels as well as UV–Vis and photoluminescence spectra of the synthesized compounds. DSC measurements revealed that the compounds form amorphous material with glass transition temperature in the range of 41–146 °C and are thermally stable up to 300 °C. β-Ketoenamines have higher glass transition temperature, smaller energy gap (2.11–2.47 eV), higher PL quantum efficiency in solution (5.25–12.97%) and ability to aggregation-induced emission than the azomethines.

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Acknowledgements

Calculations have been carried out using resources provided by Wroclaw Centre for Networking and Supercomputing (http://wcss.pl), Grant No. 18.

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Authors and Affiliations

  1. Institute of Chemistry, University of Silesia, 9 Szkolna St., 40-006, Katowice, Poland

    Mateusz Korzec, Sonia Kotowicz, Roksana Rzycka-Korzec, Ewa Schab-Balcerzak & Jan Grzegorz Małecki

  2. Silesian Centre for Education and Interdisciplinary Research, University of Silesia, 75 Pułku Piechoty St. 1A, 41-500, Chorzow, Poland

    Roksana Rzycka-Korzec

  3. Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 34 M. Curie-Sklodowska Street, 41-819, Zabrze, Poland

    Ewa Schab-Balcerzak & Mieczysław Łapkowski

  4. Faculty of Chemistry, Silesian University of Technology, 9 M. Strzody St., 44-100, Gliwice, Poland

    Małgorzata Czichy & Mieczysław Łapkowski

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  1. Mateusz Korzec
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  2. Sonia Kotowicz
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Contributions

MK conceived and designed the experiments. MK, SK, RRK and MC performed the experiments. MK, ESB, JGM and MC analyzed the data. MK, ESB, JGM and MŁ wrote the paper.

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Correspondence to Mateusz Korzec.

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Korzec, M., Kotowicz, S., Rzycka-Korzec, R. et al. Novel β-ketoenamines versus azomethines for organic electronics: characterization of optical and electrochemical properties supported by theoretical studies. J Mater Sci 55, 3812–3832 (2020). https://doi.org/10.1007/s10853-019-04210-3

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