Synthesis, Characterization, DFT Study and Antifungal Activities of Some Novel 2-(Phenyldiazenyl)phenol Based Azo Dyes
Maria Marinescu,
Claudia Valentina Popa,
Maria Antonia Tănase,
Andreia Cristina Soare,
Cristina Tablet,
Daniela Bala,
Ludmila Otilia Cinteza,
Lia Mara Diţu,
Ioana Catalina Gifu,
Cristian Petcu
Affiliations
Maria Marinescu
Department of Organic Chemistry, Biochemistry and Catalysis, Faculty of Chemistry, University of Bucharest, 90 Soseaua Panduri, 050663 Bucharest, Romania
Claudia Valentina Popa
Department of Organic Chemistry, Biochemistry and Catalysis, Faculty of Chemistry, University of Bucharest, 90 Soseaua Panduri, 050663 Bucharest, Romania
Maria Antonia Tănase
Physical Chemistry Department, Faculty of Chemistry, University of Bucharest, 4-12 Blv. Regina Elisabeta, 030018 Bucharest, Romania
Andreia Cristina Soare
Physical Chemistry Department, Faculty of Chemistry, University of Bucharest, 4-12 Blv. Regina Elisabeta, 030018 Bucharest, Romania
Cristina Tablet
Physical Chemistry Department, Faculty of Chemistry, University of Bucharest, 4-12 Blv. Regina Elisabeta, 030018 Bucharest, Romania
Daniela Bala
Physical Chemistry Department, Faculty of Chemistry, University of Bucharest, 4-12 Blv. Regina Elisabeta, 030018 Bucharest, Romania
Ludmila Otilia Cinteza
Physical Chemistry Department, Faculty of Chemistry, University of Bucharest, 4-12 Blv. Regina Elisabeta, 030018 Bucharest, Romania
Lia Mara Diţu
Microbiology Department, Faculty of Biology, University of Bucharest, 3 Intrarea Portocalelor, 60101 Bucharest, Romania
Ioana Catalina Gifu
Polymer Department, National Institute for Research and Development in Chemistry and Petrochemistry-ICECHIM, 202 Spl. Independentei, 060021 Bucharest, Romania
Cristian Petcu
Polymer Department, National Institute for Research and Development in Chemistry and Petrochemistry-ICECHIM, 202 Spl. Independentei, 060021 Bucharest, Romania
In recent decades, there has been an increased interest in azo compounds with special optical and biological properties. In this work, we report the preparation of novel azo-compounds with two and three –N=N- double bonds, using the classical method of synthesis, diazotization and coupling. The compounds were characterized by 1H-NMR, 13C-NMR, FTIR, UV-VIS and fluorescence spectra. DFT calculations were employed for determining the optical parameters, polarizability α, the total static dipole moment μtot, the quadrupole moment Q and the mean first polarizability βtot. All azo derivatives show strong fluorescence emission in solutions. The antioxidant and antifungal activities were determined and the influence of the number of azo bonds was discussed. The synthesized compounds exhibit remarkable efficiency in the growth reduction of standard and clinical isolated Candida strains, suggesting future applications as novel antifungal.
