title: The triazine-based azo-azomethine dyes; synthesis, characterization, spectroscopy, solvatochromism and biological properties of 2,2'-(((6-methoxy-1,3,5-triazine-2,4-diyl)bis(sulfanediyl)bis(2,1-phenylene))bis(azanylylidene)bis(methanylylidene))bis(4-(phenyldiazenyl)phenol).
abstract: The macrocyclic azo-azomethine dyes 2,2'-(((6-methoxy-1,3,5-triazine-2,4-diyl)bis(sulfanediyl)bis(2,1-phenylene))bis(azanylylidene)bis(methanylylidene))bis(4-(phenyldiazenyl)phenol) and its derivatives were synthesized and characterized by elemental analysis, mass, FT-IR, UV-vis and NMR spectroscopy. The solvatochromism as well as effects of substitutions on the electronic absorption of these compounds have been studied in the DMSO, DMF, THF, CH3CN, CH3OH and CH3COOH as solvents. Also they positive solvatochromism behaviors are explained on the basis of intramolecular hydrogen bonding, enol-keto tautomeric and dipole moment changes. Compounds having electron donating substituent on the phenyl ring showed good antioxidant activity. However, none of them has a considerable antibacterial activity.
authors.affiliation: Department of Chemistry, Faculty of Science, Lorestan University, Khorramabad, Iran.
authors.forename: Motaleb
authors.initials: M
authors.lastname: Ghasemian
authors.affiliation: Department of Chemistry, Faculty of Science, Lorestan University, Khorramabad, Iran. Electronic address: kakanejadi.a@lu.ac.ir.
authors.forename: Ali
authors.initials: A
authors.lastname: Kakanejadifard
authors.affiliation: Department of Biology, Faculty of Science, Lorestan University, Khorramabad, Iran.
authors.forename: Farideh
authors.initials: F
authors.lastname: Azarbani
authors.affiliation: Department of Chemistry, Faculty of Science, Lorestan University, Khorramabad, Iran.
authors.forename: Abedin
authors.initials: A
authors.lastname: Zabardasti
authors.affiliation: Department of Chemistry, Faculty of Science, Lorestan University, Khorramabad, Iran.
authors.forename: Somayeh
authors.initials: S
authors.lastname: Shirali
authors.affiliation: Department of Chemistry, Faculty of Science, Lorestan University, Khorramabad, Iran.
authors.forename: Zeinab
authors.initials: Z
authors.lastname: Saki
authors.affiliation: Department of Biology, Faculty of Science, Lorestan University, Khorramabad, Iran.
authors.forename: Sahar
authors.initials: S
authors.lastname: Kakanejadifard
mesh_terms: D000975:Antioxidants / Q000494:pharmacology; D001391:Azo Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D004396:Coloring Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D004583:Electrons; D066244:Proton Magnetic Resonance Spectroscopy; D012997:Solvents / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013696:Temperature; D013882:Thiosemicarbazones / Q000138:chemical synthesis* / Q000737:chemistry*; D014227:Triazines / Q000737:chemistry*
chemical_list: D000975:Antioxidants; D001391:Azo Compounds; D004396:Coloring Agents; D012997:Solvents; D013882:Thiosemicarbazones; D014227:Triazines; C512188:azomethine
keywords: Antibacterial activity; Antioxidant activity; Azo-azomethine schiff bases; Enol–keto tautomeric; Triazine