Phthalocyanines including 2-mercaptobenzimidazole analogs: Synthesis, spectroscopic characteristics, quantum-chemical studies on the relationship between electronic and antioxidant properties

Yakan, Hasan; ÇAVUŞ, MUHAMMET; Guzel, Emre; Arslan, Baris; Bakir, Temelkan; MUĞLU, HALİT

doi:10.1016/j.molstruc.2019.127259

Phthalocyanines including 2-mercaptobenzimidazole analogs: Synthesis, spectroscopic characteristics, quantum-chemical studies on the relationship between electronic and antioxidant properties

Yakan H., ÇAVUŞ M. S., Guzel E., Arslan B. S., Bakir T., MUĞLU H.

JOURNAL OF MOLECULAR STRUCTURE, cilt.1202, 2020 (SCI-Expanded, Scopus)

Yayın Türü: Makale / Tam Makale
Cilt numarası: 1202
Basım Tarihi: 2020
Doi Numarası: 10.1016/j.molstruc.2019.127259
Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chimica, Compendex, INSPEC
Anahtar Kelimeler: Phthalocyanine, DFT, QTAIM, Spectroscopic methods, Antioxidant activity, SINGLET OXYGEN GENERATION, AGGREGATION BEHAVIORS, IRON PHTHALOCYANINE, SENSING PROPERTIES, ZINC, ELECTROCHEMISTRY, ANTIBACTERIAL, SUBSTITUENTS, DERIVATIVES, COMPLEXES
Ondokuz Mayıs Üniversitesi Adresli: Evet

Özet

In this study, peripherally tetra 2-mercaptobenzimidazole group substituted cobalt and indium phthalocyanine complexes (2 and 3) were prepared from 4-(benzo[d]imidazole-2-ylthio)phthalonitrile (1) for the first time. Antioxidant behaviors and theoretical calculations of benzimidazole-substituted metallophthalocyanines are presented. The structures of these compounds were determined by the spectroscopic methods (IR, H-1 NMR, UV-Vis and mass spectroscopies) and elemental analysis. Antioxidant activities of the compounds (1-3) were measured using 1,1-diphenyl-2-picrylhydrazyl (DPPH) method. Antioxidant activity was followed by 1 > 3 > 2 > Trolox. In addition, density functional theory (DFT) calculations were carried out to determine the stable electronic structure, charge density distributions, FMO energy eigenvalues, and electronegativity of the ligand (1) and complexes (2 and 3). NBO and QTAIM analysis were performed to investigate the relationship between the electronic properties and antioxidant activity of the compounds. (C) 2019 Elsevier B.V. All rights reserved.