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

• Published in: Research on chemical intermediates 2019-03, Vol.45 (3), p.997-1008
• Main Authors: Bingul, Murat, Şenkuytu, Elif, Boğa, Mehmet, Uslu, Tugce Nur, Kandemir, Hakan, Sengul, Ibrahim F.
• Format: Article
• Language: English
• Subjects: Antioxidants; Carbazoles; Catalysis; Cations; Chemistry; Chemistry and Materials Science; Correlation analysis; Fluorescence; Inorganic Chemistry; Ionization; Ions; Mass spectrometry; NMR spectroscopy; Physical Chemistry; Scavenging; Synthesis; Tetrahydrofuran; Time correlation functions
• ISSN: 0922-6168; 1568-5675
• DOI: 10.1007/s11164-018-3661-0

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, 1 H and 13 C 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 ( τ F ) 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.