New 1,2,4-triazole-based azo-azomethine dyes. Part II: synthesis, characterization, electrochemical properties and computational studies.
A new series of monoiminated 1,2,4-triazole-based azo-azomethine dyes have been synthesized via condensation reaction of 4-amino-3-methyl-5-mercapto-1,2,4-triazole with various substituted azo-coupled salicylaldehyde. The dyes have been characterized by using FT-IR, UV-Vis and (1)H NMR spectroscopic methods as well as elemental analysis. The electrochemical behavior of the dyes has been investigated by cyclic voltammetry in DMSO at five different scan rates. Solvatochromic behavior of the dyes has been also investigated in four organic solvents with different polarities. Furthermore, the (1)H chemical shielding of the dyes were studied by the gauge independent atomic orbital (GIAO) method at the level of density functional theory (DFT).
Faculty of Science, Department of Chemistry, Arak University, Arak 38156-8-8349, Iran. h-khanmohammadi@araku.ac.ir
Hamid
H
Khanmohammadi
Malihe
M
Erfantalab
Atena
A
Bayat
Ali
A
Babaei
Masoud
M
Sohrabi
D000042:Absorption; D001391:Azo Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D002725:Chloroform / Q000737:chemistry; D004396:Coloring Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D055664:Electrochemical Techniques; D004583:Electrons; D006859:Hydrogen / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D013882:Thiosemicarbazones / Q000138:chemical synthesis* / Q000737:chemistry*; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
D001391:Azo Compounds; D004396:Coloring Agents; D012997:Solvents; D013882:Thiosemicarbazones; D014230:Triazoles; C512188:azomethine; C045575:1,2,4-triazole; D002725:Chloroform; D006859:Hydrogen; D004121:Dimethyl Sulfoxide