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Synthesis, photophysical and antioxidant properties of pyrrolo[3,2-c]carbazole and dipyrrolo[3,2-c:2′,3′-g]carbazole compounds

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Abstract

The synthesis of (6-ethyl-1,6-dihydropyrrolo[3,2-c]carbazol-2-yl)methanol 5 and (6-ethyl-6,11-dihydro-1H-dipyrrolo[3,2-c:2′,3′-g]carbazole-2,10-diyl)dimethanol 6 were achieved via the reduction of methyl pyrrolo carbazole carboxylate 3 and methyl dipyrrolo carbazole carboxylate 4, respectively. The structures of hydroxymethyl-pyrrolocarbazoles 5 and 6 were supported by FT-IR, matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, 1H and 13C NMR spectroscopy. The photophysical properties of the targeted compounds 3–6 were investigated by employing absorption and fluorescence spectroscopy in different common organic solvents. Also, the fluorescence lifetime (τF) of the compounds was measured utilizing a time-correlated single-photon counting technique in tetrahydrofuran. Antioxidant activities of compounds 3–6 were determined by employing three different assays, namely DPPH radical scavenging, ABTS cation radical decolarization and cupric reducing antioxidant capacity. The results revealed that the ABTS cationic scavenging activity assay was found to be the most sensitive method for the determination of inhibition values.

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Acknowledgements

We thank the Research Fund of the Scientific and Technological Research Council of Turkey (TUBITAK Project Number: 113Z159) for the financial support given to the research project.

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Dicle University, 21280, Diyarbakır, Turkey

    Murat Bingul

  2. Department of Chemistry, Faculty of Science, Gebze Technical University, Gebze, Kocaeli, Turkey

    Elif Şenkuytu & Ibrahim F. Sengul

  3. Department of Pharmaceutical Technology, Faculty of Pharmacy, Dicle University, 21280, Diyarbakır, Turkey

    Mehmet Boğa

  4. Department of Chemistry, Faculty of Art and Science, Namık Kemal University, Tekirdag, Turkey

    Tugce Nur Uslu & Hakan Kandemir

Authors
  1. Murat Bingul
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  2. Elif Şenkuytu
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  4. Tugce Nur Uslu
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  5. Hakan Kandemir
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  6. Ibrahim F. Sengul
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Correspondence to Ibrahim F. Sengul.

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Bingul, M., Şenkuytu, E., Boğa, M. et al. Synthesis, photophysical and antioxidant properties of pyrrolo[3,2-c]carbazole and dipyrrolo[3,2-c:2′,3′-g]carbazole compounds. Res Chem Intermed 45, 997–1008 (2019). https://doi.org/10.1007/s11164-018-3661-0

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